We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes in Chincoteague Island

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $251 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travellers to Chincoteague Island are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    All 109 Rentals in Chincoteague Island
    Sort by:
    Default
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    DeColores In The Pines1 / 9
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    The Bonnie Blue1 / 8
    (1)Terrible
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Grill
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***7065 Wayne Road*** Spacious rancher is pet friendly with large deck, fenced yard and internet.*** Bed Sizes: 1 Queen, 1 Double, 1 Twin, 1 Double Sleep Sofa*** Prime Season Rates: $800 weekly/$160 nightly. Off Season Rates: $650 weekly/$130 nightly. Additional amenities include: cabl...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Air Conditioning
    • Housekeeping Included
    • DVD Player
    • Washer
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SEA HARBOR: 1 mile from Assateague Island and 5 miles from beach front fun. Check-In 4pm Check-Out 12pm. This home offers large open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. It is furnished with many necessities so you can rest,...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***4379 Ridge Road*** Lovely 2 bedroom home conveniently located on Ridge Road, not far from Maddox Blvd, with many great island attractions. Perfect house for a family of 4! This house offers extra space in the large sunroom. Bright and airy, the sunroom works for both cool and warm weather. The...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Beautiful Chincoteague Island retreat1 / 15
    (18)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Porch
    • DVD Player
    • Parking
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 October 2018
    Cute little neighborhood off Main Street. It's an easy walk to the shops and restaurants downtown. Of course, the main attraction for us is always the beach at Assateague. We...
    Reviewed 5 September 2018
    Nice location walking distance to town and to the pier for fishing. Located on a quiet street. House was cozy and decorated nicely.
    See all reviews
    About this property
    Come stay and relax at this quiet retreat. This listing is a newly remodeled home which is tastefully decorated. There are three color themed bedroom's; which have two queens and two twin sized beds. There is serenity all around you, come sit on the screened in porch and relax while listening to...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Sea Treasure1 / 12
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2017
    Our first reaction walking in was relief! I booked in very late spring when there were next to no properties available so the whole way here we were holding our breath, hoping...
    See all reviews
    About this property
    ***3400 Ridge Road*** Lovely 2 Bedrooms, 1.5 Baths duplex with water views. This duplex overlooks Assateague Island with great views for the Pony Swim. This is the Best way to watch the Pony Swim and not move from your porch! Sit and enjoy the views from 2 porches. The screened porch is off of the...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Vacation House1 / 12
    (20)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Porch
    • Balcony
    • Grill
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 September 2018
    We had a great time. beautiful and comfortable house. Stunning beaches and great local food. Would definitely return!
    Reviewed 4 August 2018
    We all were very pleased with the house nice location from the beachWe took our grandson and our children for the first time it was a awesome time the house is beautiful...
    See all reviews
    About this property
    5203 Wild Pony Court. Oyster Bay II community. 2 story house located on secluded cul-de-sac. 3 bedrooms, 2 1/2 bathrooms, kitchen, laundry, living, and dining rooms, screened porch, wrap around porch, handicapped ramp, master bedroom on main floor. Private back yard and parking. Located on the...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Green Heron1 / 10
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Balcony
    • Terrace
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 July 2016
    Was very nice house Had some nice upgrades in kitchen. Bedrooms and baths met our needs. Close to beach and town attractions.. Only drawback we found was no wifi or even...
    See all reviews
    About this property
    ***4560 Shelley Cove Lane - Smugglers Cove*** Private, secluded neighborhood. Very natural wooded setting with water access available. Next door to Pine Cove Place and Serenity Now. Water access is for kayaks and canoes. 2 bedrooms and 1 bath downstairs/2 bedrooms and 1 bath upstairs.*** This...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Save time - get the best Chincoteague Island rentals sent straight to your email!
    Get the List
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Terrace
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***4446 Main Street**** Pet Friendly. Proud traditional with a water view of the Chincoteague Bay. Large appointed rooms, back deck and front screened porch.*** Bed Sizes: 2 Queen, 2 Twin, 1 Double*** Prime Season Rates: $875 weekly/$175 nightly. Off Season Rates: $650 weekly/$130 nightly....
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***3402 Ridge Road*** Lovely 2 Bedrooms, 1.5 Baths duplex with water views. This duplex overlooks Assateague Island with great views for the Pony Swim. This is the Best way to watch the Pony Swim and not move from your porch! Sit and enjoy the views from 2 porches. The screened porch is off of the...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6242 Church Street*** Proud 3 story Traditional home located at the edge of town is rich in detail and history of the island. Beautiful renovations make this home just right for the whole gang. Just a few steps and walk to shopping and waterfront downtown plaza. Spacious rooms and large...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6204 Poplar Street*** Island Cottage has a great in town location! Easy walk to historic downtown's shops and retaurants. Perfect for a budget frienldy vacation. Has Wi-Fi.*** This Property accepts Dogs 35lbs and Under Only.*** Bed Sizes: 1 Queen, 1 Double, 1 Twin.*** 2019 Prime Season...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Grill
    • Balcony
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***5505 Warren Street*** Lovely spacious3 BR canal home at Northern end of island is top notch for a delightful vacation experience. Wildlife and birdwatching throughout the day with panaramic views throughtout. Open floor plan with large dining area and back screened in waterfront porch....
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Sunset Bay Villas - Another Day in Paradise1 / 33
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We very much enjoyed our time here. We are long time visitors in Chincoteague but this was our first rental as opposed to booking separate hotel rooms for the family. We were...
    Reviewed 30 August 2018
    The location of this condo is amazing. You have gorgeous views of the bay from the living room - dinning room area and the master bedroom. The sunsets were amazing. We liked...
    See all reviews
    About this property
    ANOTHER DAY IN PARADISE CHINCOTEAGUE BEAUTIFUL BAY FRONT CONDO WITH AMAZING WATER VIEWS Owner operated by: Annie Switzer Call 240/498/0074 *** Booking Fall 2018 & Beyond *** PLEASE CONTACT ME BEFORE BOOKING SUMMER 2019 Unit 103 - 'Another Day in Paradise' Unit 213 - 'Sunset in Paradise' 2nd...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Key West Cottages1 / 4
    (14)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Balcony
    • Hot Tub
    • Air Conditioning
    • Parking
    • Shared Indoor Pool
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 December 2018
    I loved staying at the cottage. The cottage was super clean and the perfect size for two people. It’s very peaceful and the views from the peach cottage not great but nice...
    Reviewed 8 November 2018
    My husband and I had a great weekend on Chincoteague Island and absolutely LOVED the lavender cottage we stayed in. The view was breathtaking and the cottage was welcoming and...
    See all reviews
    About this property
    Beautiful cottages located in the heart of Downtown Chincoteague with views of the Chincoteague Channel and Bay. The Key West Cottages are equipped with full kitchens, cozy living rooms, Queen bedrooms and large tiled showers. Amenities such as an indoor pool, hot tub and outdoor pool next door...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Quaint Canalside Chincoteague Island Home w/ Pier!1 / 26
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Balcony
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 November 2017
    What a wonderful house to spend the week. A great place to relax after watching rockets, exploring light houses, and combing the beach. Lots of crabs to come home to. Superb.
    See all reviews
    About this property
    Leave all of your worries behind when you stay at this marvelous 3-bedroom, 2-bathroom Chincoteague Island vacation rental house! Boasting a year-round Florida room, space to sleep 8 guests, water views and a secluded canalside location with private pier, this quaint trailer-style property will...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6263 Clark Street*** Walk to everything including shopping, restaurants and entertainment from this convenient in town location! This house has been completely renovated and is a great house for your vacation, with large fenced in back yard*** Bed Sizes: 2 Queen, 2 Twin, 1 Double Sleep...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Terrace
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6248 Ocean Boulevard*** Walk to restaurants, shopping, etc. from this in town home. Nearby is Atlantic Delight and A Sea Change. WiFi Available. Upstairs offers a master suite with a private bathroom and 2 bedrooms and a full bath. 1/2 bath downstairs.*** Bed Sizes: 1 Queen, 4 Twin*** Prime...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Sea Heart & Soul, Waterfront Views, Pier and Playground at this Park Rental!!!1 / 24
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Waterfront
    • Ocean Views
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2018
    The grandkids and I really liked the condo we stayed in. We were only able to stay there one day as I had an emergency with my husband and had to leave on the second day. The...
    Reviewed 28 July 2018
    Our expectations were exceeded on so many levels. After staying at a previous location for over 20 years, that is not easy task. Sea, Heart, and Soul is conveniently located...
    See all reviews
    About this property
    Sea Heart and Soul next to Sea Adventure and Soul are 2 miles from Assateague Island and 5 miles from beach front fun. AT $229.00 per night this Rental offers open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. Located just minutes from...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Grill
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***5082 Twilley Drive*** Contemporary 4 bedroom 3 bath Waterfront home. Pet friendly, located in a private area off North Main Street. Offers 2 master suites with waterfront balconies. This home does not disappoint with its vaulted ceilings and gas fireplace. Offers a well-equipped kitchen with...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Grill
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***7518 Doe Bay Lane*** Beautiful waterview 3 bedroom, 2.5 Bath Duplex with waterside balcony, fully equipped kitchen, comfortably furnished.*** Bed Sizes: 2 Queen, 2 Twin, 1 Queen Sleep Sofa *** Prime Season Rates: $1195 weekly/$239 nightly. Off Season Rates: $775 weekly/$155 nightly. Pony...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***5169 Winder Lane*** This waterfront 4 bedroom, pet friendly home is tucked away off North Main Street. Watch the sunset from the large screened porch. Offers fenced yard, well stocked kitchen, dinign room and a spacious living room. Upstairs has master suite with private bath, 2 bedrooms and...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Shear Water1 / 12
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6347 Jester Street*** Unique Pet Friendly Chincoteague home located in town within walking distance to shops and restaurants. Has large fenced in back yard and a private outside rinse area.*** ***New HVAC-Central heating and Air for 2018*** Bed Sizes: 1 King, 2 Twins, 1 Daybed with Trundle***...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    A Summer Place1 / 18
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Grill
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 October 2014
    The pics of the home make it appear very secluded. That is not the case. It is surrounded by 4 other homes with no direct access to the water. That being said - We had nice...
    See all reviews
    About this property
    ***5094 Blake Point Road**** Timeless Traditional home dates back to the turn of the century. Renovations have upgraded this fine 4 bedroom home that is also pet friendly and sleeps 10. Grand views of the Chincoteague Bay with large front screened porch and decks off both levels. Very quiet and...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6201 Ocean Blvd*** Bring your four legged friend to this well-appointed home within walking distance to restaurants, shops, and more! This is a great pet friendly house right in the heart of downtown. It offers DSL Wi-Fi and a fax machine in the separate sitting room off of the living room. The...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
    Make Enquiry
    Big Pines1 / 9
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 November 2015
    Well maintained home within walking and biking distance of many shops and restaurants. Lovely screened in porch and the fire pit was an added bonus.
    Reviewed 26 September 2014
    I have went to chincoteague yearly since i was born and by far this is the first place i am going to stay for now on. Walking into this home i fell in love and instantly wanted...
    See all reviews
    About this property
    ***3545 Willow Street*** Very nice, comfortable 2 BR home will delight you with it's updated kitchen and new appliances. The large screened-in back porch with gas grill. Deck will accommodate outdoor entertaining. Centrally located, it is a short walk to town/shopping and the carnival grounds. 3...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6582 Church Street*** Lovely spacious home with 2 enclosed sunporches. Large kitchen for those looking to cook. Nice back deck and 1st level bedrooms. 3rd bedroom is loft area. Close to town & shopping but very quiet and private setting. 2 bedrooms and 2 baths downstairs (includes master bed...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    East Wing1 / 11
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 June 2018
    Absolutely amazing loved this place, cute comfortable family home. Minutes from everything. Would stay here again. Also recommend to anybody. You will be very pleased
    See all reviews
    About this property
    ***5159 Deep Hole Road*** This charming island cottage built in 1920 features wood plank floors, open-beam ceilings, a screened-in porch and a large yard. Llovingly restored, East Wing is within walking distance of Little Oyster Bay, a boat launch, playground, restaurants and the best ice cream...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Egret's Walk1 / 9
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 2016
    This was a much needed vacation that our family of five looked forward to and will remember for years to come. The price was appropriate for the clean and quaint home. Staying...
    See all reviews
    About this property
    ***5368 Main Street*** Very enjoyable and immaculate traditional home will delight you stepping inside. Pet Friendly! Newly added Fenced in Back Yard and Wi-Fi. 1 bedroom and 1 bath downstairs/1 bedroom upstairs.*** This Property accepts Dogs 35lbs and Under Only.*** Bed Sizes: 1 Queen, 3...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Goose Bay1 / 12
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 2018
    We enjoyed an idyllic week at Goose Bay with our family, enjoying meals on the porch watching the sunset!
    See all reviews
    About this property
    ***5104 Blake Point Road*** Goose Bay tucked away off the northern end of Main Street offers a year round nature reatreat. The raised home with skylight and huge picture windows capture light and outstanding water views and sunsets over the Chincoteague Bay and its wild grassy marsh and ponds....
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Kate's Cottage1 / 11
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 September 2018
    We stayed at Kate's Cottage the last week in August with our daughter, her two boys and our 24 pound Sheltie. The place was absolutely perfect for us! There were two bedrooms...
    See all reviews
    About this property
    ***5348 Oak Drive-Piney Island*** Tucked away in Piney Island Just minutes from Assateague's nature trails and beach. Wireless internet and water access for canoe and kayak. Pet Friendly! New bedroom and bathroom added in 2013. All bedrooms on same level.*** Bed Sizes: 1 Queen, 1 Double, 2...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Mystical Sand1 / 10
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 January 2018
    We love staying at this lovely little home Very clean! the painting really made you feel like you where at the beach at all times. and close to a couple of the stores so easy...
    Reviewed 11 July 2017
    We (my wife, son, mother-in-law, wife's aunt, and myself) stayed here last summer. My son was only a year old so it was really only 4 full grown people. We loved the location...
    See all reviews
    About this property
    ***6096 Taylor Street*** Perfect retreat for the traveler on a budget! Tastefully decorated cottage with 36 inch television and within walking distance of shops and restaurants. All bedrooms on same level.*** Bed Sizes: 1 Queen, 2 Twin, 1 Queen Futon*** Prime Season Rates: $650 weekly/$130...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***4264 Pine Street*** Tucked away home close to town with large screened porch. 1 bedroom and sleeping porch area downstaris and 1 bedroom and sleep landing upstairs.*** Bed Sizes: 1 Queen, 1 Double, 4 Twin*** Prime Season Rates: $750 weekly/$150 per night. Off Season Rates: $495 weekly/$99 per...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Make Enquiry
    Pony Swim1 / 12
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2018
    We rented Pony Swim for the last week of August 2018. The house was amazing! Great location, very clean with plenty of room! It is located right on the water with a large...
    See all reviews
    About this property
    ***7460 Pony Swim Lane*** Waterfront duplex with deep water dock and great views of Assateague Island and Lighthouse. Newly remodeled kitchen, living room, and dining room. Now offers wireless interenet. 2 bedrooms and 1 bath upstairs, 1 bath downstairs.*** Bed Sizes: 1 Queen, 4 Twin*** Prime...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Refuge1 / 12
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2017
    The Refuge was a beautiful, serene place. The house was in a wonderful setting that allowed for many quiet mornings...days....and nights sitting on the deck. ❤️
    Reviewed 17 August 2015
    The Refuge has a beautiful and secluded setting on the water, with many windows to admire the views from, and 2 decks. The living room was spacious and comfortably furnished...
    See all reviews
    About this property
    ***5187 Oak Spring Lane*** Refuge is no exaggeration with this luxury top of the line four bedroom waterfront home. Two luxury master bedrooms lead out to waterfront decks. Grand views of the Chincoteague Bay and access for kayaks and canoes, jacuzzi tub in master bedroom, 2 gas fireplaces and over...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Terrace
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***3620 Main Street*** Extraordinary custom built Water front home. Enjoy the sunsets from the two level covered porches or from your private dock! With 4 bedrooms and 4 baths, beautiful interior with chef’s kitchen, large dining and living areas. Plenty of parking, large back yard. Great...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***3757 Willow Street*** Completely renovated traditional home in town with bright cheerful rooms and offers all amenities. Pet friendly! Two bedrooms on second level of home and two walk thru third story bedrooms. Third story loft with 4 twin beds has a typical Traditional home steep staircase....
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***4265 Pension Street*** Charming, traditional island home near town. Walking distance to shops, restaurants, and waterfront. Perfect for gathering family/friends!! Near Cattail Cottage, Miss Niccies, Time Out, and Rhinos Retreat. 4 bedrooms upstairs/2 baths downstairs. Bed Sizes: 1 Queen, 2...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6301 Circle Drive*** Charming pet friendly cottage in serene island setting with easy access to the Beach and to the Old Town. Spacious yard and screened porch. 2 full bathrooms. Bedrooms include 1 large master BR with king-size; plus 1 BR with 2 twins; and a cozy den with sofa/sleeper. Pet...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***3241 Lekites Drive*** Lovely, spacious home tucked away off Main Street with large deck and 15 by 30 ft pool. 3 bedrooms and 2 baths upstairs (includes master bed and bath), 1/2 bath downstairs. Has WiFi*** Bed Sizes: 2 Queen, 1 Bunk*** 2019 Prime Season Rates: $1425 weekly/$285 nightly. Off...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Tuck Inn1 / 4
    (2)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 August 2018
    Tuck Inn was great. It was our first time there. We have spent many summer weeks in Chincoteague and this place was the most "Chincoteaguey" of them all! Rustic and full...
    Reviewed 17 June 2016
    The house was nice but was older. It had the old beach house charm which we all loved. We had 3 kids with us (ages 3, 5, and 7). They all slept upstairs which was a little...
    See all reviews
    About this property
    ***6559 Church Street*** Island home with large back yard and deck and Internet. Pet Friendly! Nearby is Chincoteague Crossing. 2 bedrooms and 2 baths downstairs/2 bedrooms upstairs.*** Bed Sizes: 1 Queen, 1 Double, 4 Twin*** Prime Season Rates: $795 weekly/$159 per night. Off Season Rates:...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6402 Teal Lane*** The unobstructed view of Eel Creek and Little Oyster Bay will get your attention at sunrise and sunset! Put your kayak in the water at the shared dock at high tide. Now has WiFi and 42' TV*** This Property accepts Weekly Rentals Only.*** Bed Sizes: 2 Queen, 1 Bunk Bed...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Winder Station1 / 17
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2018
    Spent 2 weeks and the house was great. Suggest the owners provide a better description of the layout and photos because it is better than it looks in the current photos. The...
    Reviewed 3 June 2018
    This house has healthy but quirky old bones, and that´s just why we loved it. The location is convenient without any disturbing bustle or noise. There were some items in need of...
    See all reviews
    About this property
    ***5165 Winder Lane*** Enjoy the sunsets from this new waterfront home, tucked away off North Main Street. Private setting and pet friendly(2 pet maximum).Water access for kayaks and canoes. 2 bedrooms and 1 bath downstairs/1 bedroom and 1 bath upstairs.*** Bed Sizes: 1 Queen, 2 Double, 1 Queen...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6314 Cropper Street*** Lovely renovated 3 story Victorian combines classic charm with affordable luxury located in the heart of downtown Chincoteague.*** Bed Sizes: 2 Queen, 2 Twin*** Prime Season Rates: $1000 weekly/$200 nightly. Off Season Rates: $800 weekly/$160 nightly. Additional...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Sweet Retreat:  Delightful Chincoteague Cottage-Pets Considered1 / 30
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • Private Garden
    • Wi-Fi
    • DVD Player
    • Grill
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2018
    The quiet, the comfort, the warmth...they all helped my wife relax enough to finish up her second book. And I had a blast in the well-stocked kitchen. Pretty much anything I...
    See all reviews
    About this property
    Sweet Retreat is part of of the owner managed properties of O'Connor Properties. We have hosted over 150 guests in Sweet Retreat over the last 3 years and have graciously received many five star reviews. * Perfect for a romantic getaway * 3 bedrooms, 2 bath, marsh-view home, located in...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shoes Off is an adorable 2 bedroom, 1 1/2 bath, central air conditioned town home located on a cul-de-sac, adjacent to Maddox Blvd., that sleeps up to 5 people with 1 Queen, 2 Twin, and a Childs Chair Bed. This fully stocked, nicely furnished town home is an end unit with a large back yard, perfect...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***5421 Deep Hole Road -downstairs apt*** Secluded, quiet location with lots of yard for a pet. Pet Friendly!*** Bed Sizes: 1 Queen, 1 Double, 1 Sleep Sofa*** Prime Season Rates: $550 weekly/$110 nightly. Off Season Rates: $400 weekly/$80 nightly. Additional amenities include: dvd vcr/dvd,...
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***7175 Bunting Road*** Totally upgraded townhome with large back enclosed sun porch. Nice wetland view! 2 Bedrooms and 2 baths upstairs. Has Wi-Fi.*** Bed Sizes: 1 King, 1 Queen, 1 Queen Sleep Sofa, 1 Twin Rollaway, 1 Twin Sleep Sofa.*** Prime Season Rates Only: $740 weekly/$148 nightly....
    View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    1
    Island holiday rentals - seaside villas, waterfront homes and condos

    Browse through our holiday home rentals, and you’ll discover some very tempting choices for your family holiday. An historic Main Street home is surrounded by a private landscape with a screened porch, bikes and beach toys. A luxurious custom home overlooks beautiful Oyster Bay, and family-friendly condos feature waterside decks, swimming pool and marina.

    Abundant outdoor recreation and attractions

    Naturally, the seashore is the dominant focus for outdoor fun on Chincoteague Island. Fish from the dock or walk the beach. Take a bird-watching hike or bicycle ride through wildlife preserves and quaint island lanes. Enjoy dolphin watching, island tours and spectacular sunset views from your own guided cruise through remote bays and waterways. Either Assateague or Chincoteague beaches are ideal for family picnics and water sports.

    Believe it or not, the wild Chincoteague Ponies are an unusual attraction on adjacent Assateague Island. The kids will love a trip to the Chincoteague Pony Center to enjoy pony rides, a show and riding competition. Book a small, charter deep-sea fishing trip that offers the opportunity to land big game fish from mahi-mahi and tuna to marlin and sharks.

    Leisurely shopping and dining

    As a contrast to all of that outdoor adventure, explore the village feel of the historic downtown and Maddox Boulevard areas. You’ll find exceptional hand-crafted duck decoys and original wildlife and landscape paintings and charming gift shops. To keep you entertained on a lazy sun-filled afternoon, stop in at Sundial Books to browse for book favorites and enjoy a cup of coffee or tea.

    Fresh ocean fare dominates local restaurant menus that are loaded with clams, oysters, and all-you-can-eat seafood platters. Of course, you can’t take the kids on holiday without finding the perfect pizza place, and that would be Famous Pizza Family Restaurant. They’ve been serving home-fresh pizza, cheese steaks and more for over 30 years. And you positively have to stop in at The Sea Shell Café for a gourmet salad and authentic Smith Island Cakes. They even cater to your holiday home, if you want to skip the kitchen duties and enjoy their excellent dinner selections.

    Villa and home rentals – the perfect seashore holiday choice

    There is no better way to enjoy a lazy, leisurely island holiday than from your carefully-chosen home rental. You’ll have plenty of room to relax, waterside views to enjoy and some wonderful home-grilled meals or bountiful breakfasts that will long be memorable for your entire family.

    List your property
    Owner log in