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.

Chestertown House Rentals

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
    $563 Average
    |||
    |||
    $0$2,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Chestertown area holiday rental. You're so close to securing your perfect getaway. Book today.
    13 Matching Rentals in the Chestertown AreaView all 33 rentals
    Sort by:
    Default
    Loon Lake Retreat with Private Dock1 / 36
    (18)Excellent
    Chestertown
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    The following rentals are within 15 kilometres of Chestertown.
    Gore Mt Ski House with all the amenities! Ask about our long term rates.1 / 17
    (3)Excellent
    North Creek
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Beautiful Log House In Bolton In Lake George1 / 16
    (2)Very good
    Bolton Landing
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Hot Tub Under the Stars1 / 24
    (22)Very good
    Johnsburg
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Balcony
    • DVD Player
    • Hot Tub
    • Internet Access
    • Patio
    • Porch
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 October 2017
    Looking for a cabin in the Adirondacks with all the amenities (full kitchen, multiple bedrooms, wifi, television, etc.), privacy, and a top-notch hot tub? I was and I found it...
    Reviewed 14 February 2017
    Steve is the best host possible and made the trip easy and convenient. I really appreciated his kindness and all the good advice he gave me for my trip. The cabin is nicer...
    See all reviews
    About this property
    Nestled in 10 acres of woods, our cabin provides a rare blend of country luxury, peace and tranquility. A hot tub under the stars awaits you after a long day on the slopes, mountains or water. There are three porches for star gazing and a large firepit for roasting marshmallows. Come inside...
    View all property information
    Location Information
    Johnsburg, New York 12853
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    HIGHLANDS CASTLE overlooking beautiful Lake George1 / 132
    (7)Excellent
    Bolton Landing
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Patio
    • Porch
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    After receiving some fairly bad news, my husband wanted to take me away to a tranquil, peaceful and beautiful place to take my mind away from things. He discovered The Highlands...
    Reviewed 28 January 2018
    So I booked this castle for my husbands birthday which was on jan.It snowed and was raining so the roads turned to black ice. However we called John who is the owner to help us...
    See all reviews
    About this property
    RENT-A-CASTLE! HIGHLANDS CASTLE is the most extraordinary estate you'll ever find... A treasure beyond words with the intrigue and allure which only a castle can offer. Experience the peaceful tranquility that surrounds this property and the most spectacular view in the world! YOU PROVIDE...
    View all property information
    Location Information
    Bolton Landing, New York 12814
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    North Creek
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Housekeeping Included
    • DVD Player
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A spacious house located in the heart of North Creek. Location, location, location!! Gore Mountain is 5 minutes from the house, you can even have the shuttle pick you up or drop off during the main season. White water rafting van pick up/drop off also within a short walking distance from the...
    View all property information
    Location Information
    North Creek, New York 12853
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
    Make Enquiry
    Take a Break in Bolton Landing!1 / 17
    (2)Very good
    Bolton Landing
    4 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Balcony
    • Housekeeping Included
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 October 2015
    The home was very nice. It is also a great location. Within walking distance of restaurants/stores and the lake. Lots of sleeping room. I would definitely recommend to...
    See all reviews
    About this property
    Our home is spacious, clean, comfortable and located within walking distance to Lake George and downtown Bolton Landing. Located close to the action; fishing, hiking, hunting, horse races, golfing, or just relaxing and enjoying all that the Lake George region has to offer. We provide all high...
    View all property information
    Location Information
    Bolton Landing, New York 12814
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 10
    Make Enquiry
    Adirondack Getaway Sacandaga Lake 1/2 hr Saratoga,1 / 43
    (2)Very good
    Adirondack
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Washer
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 May 2017
    We rented this cabin for my wife's 40th birthday. She wanted to do something that the kids could do as well and this was a good choice. It was a short distance from where we...
    See all reviews
    About this property
    20 minutes north of NYS Thruway, Exit 27-Amsterdam Woods Hollow Rd. is North, about a mile past intersection of Rt. 29 & Rt. 30 Address: 218 Woods Hollow Rd., Gloversville, NY 12078 100 x 200 ft. lot with no houses behind, surrounded by 130 ft. pine trees, very peaceful and quiet Adorable...
    View all property information
    Location Information
    Adirondack, New York 12078
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Gore Mountain ,North Creek, Lake George, Saratoga1 / 16
    (7)Very good
    North Creek
    6 Bedrooms, 3 Bathrooms, Sleeps 20 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minutes from Speculator, Gore Mountain & Schroon Lake, 1/2 hour to Lake George, and 40 minutes from Saratoga!! Lots of custom woodwork - you'll love it! !! 6 bdrms (5 bedrooms have 2 queen or full beds in each & 1 twin bed in an alcove on 3rd floor),3 full baths (2 with showers and 1 with...
    View all property information
    Location Information
    North Creek, New York 12853
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 20
    Make Enquiry
    Bolton Landing
    2 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Washer
    • Mountain Views
    • Private Garden
    • Housekeeping Included
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    While driving down Acorn Drive, you immediately sense that excitement you felt as a child when searching for that perfect campsite. You are overwhelmed by the abundance of tall pines and that crisp, clean air that only comes from being in the Adirondacks. You then approach a lovely Adirondack Cape...
    View all property information
    Location Information
    Bolton Landing, New York 12824
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Save time - get the best Chestertown rentals sent straight to your email!
    Get the List
    Johnsburg
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Balcony
    • DVD Player
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LOCATION LOCATION LOCATION! Come stay at our cozy cabin nestled in the woods located on 6 acres right across from the Hudson River and only 5 miles to Gore Mountain Skiing! Listen to the brook that flows through the property while toasting marshmallows in the fire pit. There is a bedroom on the 2nd...
    View all property information
    Location Information
    Johnsburg, New York 12853
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Bolton Landing
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You provide the Fairy Tale and we'll provide the Castle... THE CASTLE GATEHOUSE sits below Highlands Castle surrounded by nature and the privacy that goes with it. A treasure beyond words with the intrigue and allure which only a castle can offer! Poised on a graceful mountaintop less than 1/2...
    View all property information
    Location Information
    Bolton Landing, New York 12814
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    Lake George 4-Bedroom Waterfront Home1 / 22
    (7)Excellent
    Bolton Landing
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Mountain Views
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2017
    We loved this house. It was so comfortable, clean and well-appointed and well-stocked. We were two families totaling 8 people and never once felt crowded.The front porch is a...
    Reviewed 19 July 2015
    Our family had a great stay in this beautiful house. The view and decor won't let you down and are as advertised. The house is very comfortable, spacious, and clean. This house...
    See all reviews
    About this property
    “Vista View” 41 Norowal Road Bolton Landing, NY 12814 For Weekly Rentals or Long-term Lease Custom built, two-story, four-bedroom, two-and-a-half bath Lake George waterfront home constructed in 2008. Eight people maximum capacity. NO PETS and NO SMOKING allowed. $4,400. per week...
    View all property information
    Location Information
    Bolton Landing, New York 12814
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    List your property
    Owner log in