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.

Pet Friendly Holiday Rentals in Chatham

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
    $517 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travellers to Chatham are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    99 Matching Rentals in ChathamView all 459 rentals
    Sort by:
    Default
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Cape Escape Chatham Walk to Beach! Private-Newly Renovated-Hear Waves at Night1 / 53
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    #602: Make memories in this Chatham beach home within steps to Nantucket Sound!1 / 32
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Beach Chic Cape Escape! Chatham 5 Star Private-Newly Renovated 5m walk to beach1 / 54
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Grill
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 September 2016
    What a unique & wonderful house in Chatham!  John & Ruby are really superb hosts, very accommodating, making sure we were all set… to our delight, John even texted to let...
    Reviewed 3 May 2016
    Plusses:* Kitchen is fully equiped and the stove is big and of excellent quality.* Showers have a lot of power.* Good size house (big living room, separate dining room, big...
    See all reviews
    About this property
    Newly renovated kitchen with quartz “Sea Glass” countertops, backsplash and Nantucket farm sink. Truly a well equipped cooks kitchen. This year round low allergen, open concept home has 3 bedrooms, 2 newly updated baths, a large two level outdoor deck with electric retractable awning, creating a...
    View all property information
    Location Information
    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Breathtaking riverfront dog-friendly home w/ a lovely deck, close to the beach!1 / 29
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Parking
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 September 2017
    Very nice Chatham, Cape Cod home with great views, and not too far from town. A comfortable home that I would rent again, and the managment company was good about staying in...
    See all reviews
    About this property
    Experience a glimpse of Cape Cod waterfront living at this three-bedroom Chatham home, a dog-friendly property with a wrap-around deck, panoramic views of the ocean and Oyster River, and nearby access to Harding's Beach. This quaint two-level home is scenically situated between Nantucket Sound and...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pretty, shabby chic, sunny cottage and barn on private two acres of land down quiet country road. Brand new six person hot tub on deck, in time for fall or winter rental. The grounds are naturally landscaped, not manicured, no chemicals used. Enjoy the serenity of the undisturbed woods, open floor...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come Stay at: The Crow's Nest! Dog Friendly! Spend Lazy summer days at this Cape Cod Vacation rental in Chatham. With the shade from the pines, the spray of sea salt from the Nantucket Sound and the warm summer sun, you are sure to have a relaxing escape to the Cape. From kayaking (2 included!) to...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Private Garden
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Friday to Friday Rental This cottage is converted out of an a barn built in 1792. The upstairs bedroom has a full bed and the downstairs bedroom has a day bed (2 twin beds). This cottage is not for everyone. The entrance to the upstairs bedroom is steep and 18' wide. You can see it next to the...
    View all property information
    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Save time - get the best Chatham rentals sent straight to your email!
    Get the List
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Cranberry View! Pet Friendly (dogs only please).  Relax in this 3 bedroom, 2 bath Cape Cod Vacation home in Chatham that is convenient to downtown Chatham and beaches. Privacy abounds just off Main Street and the home even overlooks a working Cranberry Bog! Window AC units in Bedrooms...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    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
    • Parking
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    241 Training Field Road PET FRIENDLY Charming and updated 3 bedroom air conditioned ranch style home, just 1 mile from beautiful Pleasant Bay at Jacknife Point Beach. $1900 per week in season * $160 Cleaning Fee * $100 Handling Fee * $55 Damage Insurance OR $500 Security Deposit Please contact...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    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
    • Grill
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Tide After Tide. Pet Friendly! Private, Family Ranch-Style Riverbay home in Chatham for your Cape Cod Vacation! Located on a peaceful, residential, dead-end road. As you enter the through the front door you will find comfortable seating in the living room with a flat screen TV and...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 5 bedroom, 3 bath Chatham rental home has incredible water views of Taylor's Pond. The home is surrounded by oak trees creating a very private setting. There is a spacious deck with dining table for dining alfresco. A path offers direct access to Taylor's Pond for kayaking, canoeing or...
    View all property information
    Location Information
    Chatham, Cape Cod 02659
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    3 Bedrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Air Conditioning
    • Washer
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rate (Cleaning Fee Included): In-Season: $1550 per week ~ No Off-Season Click for More Photos, Map, and Availability Calendar Enjoy your Chatham summer vacation in this light and bright vacation home. Located on a quiet side street, on the way to Ridgevale Beach, one of Chatham's most...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Classic Chatham Charm -- Walk to Beach & Town! (Linens included) Peak Summer Weekly Rates: $5,310 - $6,750 (Pets Considered)  Rents Saturday to Saturday during peak season SELECT WEEKS JUST REDUCED 10%! (click the rates tab for the new rates) Located in a premier Chatham Village location, this...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Grill
    • Parking
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW Located just steps from family-friendly Ridgevale Beach, this charming 2BR/1.5BA cottage offers a quintessential Chatham vacation. The walk to the coast is short and the shops and restaurants of downtown are just a quick drive away! Spend your days at the picturesque beach...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This traditional two bedroom, one bathroom Cape Cod cottage is just .4 miles from popular Ridgevale Beach. This one floor cottage has open dining and living rooms (new couch and chair coming for 2018) with flat screen TV, small kitchen with new stove for 2018, bathroom with shower stall, and two...
    View all property information
    Location Information
    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Washer
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great Vacation Spot Right up the Road from Pleasant Street Beach in South Chatham! Well appointed and comfortable, this home is convenient to all the area has to offer. Enjoy grilling on the deck in the private backyard after a day enjoying summer on Cape Cod! Four bedrooms and 2 1/2 bathrooms...
    View all property information
    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    6 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    209 Champlain Rd Chatham MA DOG FRIENDLY Great, rambling home with an old-Cape Cod feel located on the 'loop' just around the bend from Stage Harbor. Wonderful area to enjoy while here on the Cape! A tennis court is available to tenants during daytime hours from 10 am to 5 pm. The huge, grassy...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 11
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Grill
    • Parking
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this lovely Chatham vacation rental located in desirable North Chatham near, gorgeous beaches, restaurants & Chatham Village. Here you can enjoy everything Chatham has to offer, from Chatham baseball games, the village area with restaurants & shops, Lighthouse beach & more! Gorgeous...
    View all property information
    Location Information
    Chatham, Cape Cod 02650
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Waterfront
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $8450 per week Off-Season: $5950 per week Click for More Photos, Map, and Availability Calendar Stunning home located in Chatham's prestigious Stage Island neighborhood. Gaze out at Stage Harbor from almost every room in the house! It features a...
    View all property information
    Location Information
    Chatham, Cape Cod 2633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
    Make Enquiry
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Chatham Village Classic, Behind Lighthouse (Pets Considered)  Peak Summer Rates: $5,300 - $5,500 Just REDUCED! Rates for select open weeks lowered by 10% (see new rates in the rates tab) Rents Saturday to Saturday during peak season This grand Chatham Village family home is located in Chatham,...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Outdoor Dining Area
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pet Friendly! Classic Cape Cod Vacation Home Rental in Chatham near Schoolhouse Pond for freshwater swimming.   Located in a residential area and convenient to the Cape Cod Bike trail, and the Chatham Airport and restaurant (Hanger B eatery). It has 3 ac units in the main floor bedrooms and free...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    3 Bedrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Washer
    • Patio
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rate (Cleaning Fee Included): In-Season: $1575 per week ~ FRIDAY TO FRIDAY Click for More Photos, Map, and Availability Calendar Bright, cheerful home with a peek of Pleasant Bay from the back deck. Swimming and Kayaking in Pleasant Bay is right down the road at Jackknife Beach! This...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Washer
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $2375 per week No Off-Season Click for More Photos, Map, and Availability Calendar Centrally located, this lovely updated three bedroom home is a wonderful spot for your Chatham vacation! Only one mile from everything downtown Chatham has to...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 7
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pet friendly home with central air Comfortable 4 bedroom cape on a quiet street in Riverbay Estates. Convenient to Schoolhouse Pond and Jackknife Cove beach on Pleasant Bay. This home has central air conditioning, an enclosed outside shower, and is PET FRIENDLY. $1650 per week * $100 Handling...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 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
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of Chatham Village with its many delightful shops, galleries, and restaurants this 2 bedroom home is close to everything Chatham has to offer. Enjoy a short stroll to Lighthouse Beach, the Chatham Fish Pier, tranquil Mill Pond or the Orpheum Theatre. The first floor offers a...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    3 Bedrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $1,975 per week Off-Season: $1,425 per week Click for More Photos, Map, and Availability Calendar Enjoy the simple life in this classic, Chatham cottage. Located in the popular Hardings Hills neighborhood, a quick walk down to Hardings Beach!...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Parking
    • DVD Player
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Cape Escape! Pet Friendly! Walk to Harding's Beach from this Chatham Vacation Rental Home. 4 Bedrooms, sleeps 8. Access to association dock and picnic area in Harding's Hills Association. AC units in 3 bedrooms and the main living area, there is cable and free WiFi too. Calling all...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Washer
    • Parking
    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming cape-style pet friendly home close to all that the village has to offer. PET FRIENDLY charming cape-style home close to all that the village has to offer. Close to town, Oyster Pond, Chatham Anglers games, golf, and tennis courts. Enclosed outdoor shower and patio with outdoor dining- 4...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    4 Bedrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $2225 per week Off-Season: $1525 per week Click for More Photos, Map, and Availability Calendar Weekly rentals from mid-JUNE to mid-SEPT Charming home located in terrific central area of North Chatham. Walk to Ryder's Cove boatyard. Beautifully...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 12
    Make Enquiry
    14 Hallett Lane Chatham Cape Cod - Sand Simeon1 / 48
    (6)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Private Outdoor Pool (Heated)
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 May 2017
    Wow! We were impressed from the moment we walked through the door. The home is quite large, very well appointed and was very clean. We met people there and the home was great...
    Reviewed 12 May 2017
    This home was perfect for our group! Great space to have the group all together but at the same time when rooms are spread out so the home doesn't feel crowded with large groups...
    See all reviews
    About this property
    Come stay at: Sand Simeon. Pet Friendly! Relax and enjoy this Chatham, Cape Cod Vacation Rental Home offering 6 bedroom 6.5 bathrooms.  Bonus: Linens (bed sheets and bath towels) are complimentary with this home for the Peak Summer Season. This luxury home is pet friendly with a private pool,...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
    Make Enquiry
    201 Main Street Chatham Cape Cod - Sandpiper1 / 42
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the Sandpiper! Pet Friendly! 4 bedroom, 4.5 bath Vacation Rental located in the heart of Chatham's historic village!! BONUS: LINENS INCLUDED IN SEASON. Whether you are soaking in the hot tub on the private patio or enjoying an outdoor shower after you've come home from Lighthouse or...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    ENCHANTING COTTAGE FOR 4 CLOSE TO FOREST BEACH IN CHATHAM! PET FRIENDLY!1 / 16
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2017
    Pet friendly, clean, and the beach is a walk away! All amenities available at the house: grill, beach toys, games, etc. We loved our stay!
    See all reviews
    About this property
    AFFORDABLE DREAM BEACH HOUSE IN CHATHAM WITH LARGE FRONT AND BACK DECKS, ROOM FOR 6, AND ONLY STEPS TO FOREST BEACH! PET FRIENDLY! There is a dreamlike quality to this 3 bedroom/1 bath cottage just down the road from Forest Beach in Chatham. Maybe it's the storybook shutters flanking every bedroom...
    View all property information
    Location Information
    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Grill
    • Wi-Fi
    • DVD Player
    • Patio
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to: Sandy Paws! Pet Friendly. Newly renovated with Central air (Slim line units). Come have some fun in the sun at this Cape Cod Vacation home in Chatham! You will enjoy deeded access to the 'Little Beach flats'. Just moments away from the top attractions near our Chatham vacation rentals,...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This quaint 3 bedroom, 2 bath house is a quick ride to Jacknife Beach, fresh water Schoolhouse Pond or downtown Chatham. Amenities include central a/c, washer, dryer, dishwasher, Wi-Fi, cable TV (includes sports and weather) and a DVD player. The yard is nicely manicured with a spacious lawn,...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • Patio
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $3,175 per week No Off-Season Click for More Photos, Map, and Availability Calendar Recently renovated three bedroom home with beautiful views of Red River Marsh and Nantucket Sound! Filled with new furnishings and appliances, this spacious home...
    View all property information
    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, Sleeps 7
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in a prime in-town location.   This Cape Cod Vacation Rental Cottage complex is just steps to the Mill Pond (a saltwater inlet of Nantucket Sound) in Chatham's Old Village and a few blocks to beautiful Lighthouse Beach. This desirable and newly renovated family compound built by a famous...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    151 Sky Way Chatham Cape Cod1 / 47
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 July 2017
    Conveniently located on the outskirts of Chatham, 151 Sky Way is the perfect location for a relaxing vacation. The house is immaculate, it is extremely well equiped and very...
    See all reviews
    About this property
    Waterfront & Dog friendly! Sleeps 8! This newer Cape Cod Vacation Rental home in Chatham offers panoramic views and backyard access to beautiful Blue Pond and deeded access to White Pond, perfect for swimming, kayaking, canoeing and fishing. Comfort and convenience inside and out define this home,...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Chatham Family Compound Sleeps 16   SAVE UP TO $1,000+/WEEK!  RATES SHOWN INCLUDE ADJUSTMENTS FOR OPEN WEEKS ONLY.  Walk to Beach – Linens Included Peak Summer Weekly Rates: $13,500 - $13,900  Rents Saturday - Saturday during peak season   Please click on the 'Virtual Tour' to see a 3D tour of...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
    Make Enquiry
    44 Cranberry Way Chatham Cape Cod - Venture Inn1 / 34
    (2)Very good
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 April 2017
    With family and friends out for our daughter's wedding in Boston last September we wanted a place immediately afterward for an extended reunion. It was all made possible on a...
    Reviewed 15 April 2017
    My boyfriend and I rented this home with two other couples for a relaxing getaway in our favorite spot on Cape Cod - Chatham!The house was so beautiful and newly renovated...
    See all reviews
    About this property
    Central Air and Dog Friendly! Totally Updated 5 Bedroom Cape Cod Vacation Rental Family Home in Chatham on the way to Cockle Cove Beach. Large family? No problem! Can't leave home without Fido? Bring your doggie along! Everything is here to for you and your group to have a great vacation at...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    10 Cove Hill Chatham Cape Cod - The Salty Dog1 / 51
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Waterfront
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 April 2017
    We were looking for a pet friendly place to get away for a long overdue vacation and the Salty Dog fit the bill quite nicely. The pictures cannot capture the beauty of the...
    Reviewed 4 April 2017
    This beautifully furnished, casually comfortable rental feels like home! In an idyllic setting on the water, close to beaches and town, we are in love with the property! Plenty...
    See all reviews
    About this property
    Experience 'The Salty Dog'. Luxury at its finest. This 4,000 square foot, pet friendly, waterfront 4 bedroom/4 bath home sleeps 10. You will find Central Air, WiFi, and all amenities at this Chatham Vacation Rental Home, everything for a great Cape Cod Vacation! BONUS: LINENS INCLUDED IN SEASON....
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy Family Tides, this pet friendly, updated, 4 bedroom home sleeps 10. Walk to Harding's Beach with deck and outdoor shower. AC units. Free WiFi too.  Walk to Harding's Beach from this Cape Style home! Enter into the open dining room with seating for 6-8 + 2 at the breakfast bar. One step down...
    View all property information
    Location Information
    West Chatham, Chatham 02669
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    4 Bedrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Washer
    • Air Conditioning
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $3225 per week Off-Season: $2325 per week Click for More Photos, Map, and Availability Calendar Private, traditional style Cape house in the peaceful Sears Point area of Chatham. It has a lovely sun porch, a spacious living room and a lovely...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Light & Bright Chatham Home, Walking Distance to Beach Linens Included, Pets Considered Peak Weeks - $2,000 Rents Saturday - Saturday during peak season Please note:  This property is part of a larger estate, and is only available to rent individually in the months outside of July and August...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    4 Bedrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • DVD Player
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $2825 per week Off-Season: $2025 per week Click for More Photos, Map, and Availability Calendar Charming, antique home located in North Chatham with a pretty, private yard and distant views of the ocean from large deck. Short walk to Cow Yard...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, Sleeps 10
    Make Enquiry
    1
    List your property
    Owner log in