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.

East Chatham Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
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
    Price
    per night
    $234 Average
    $0$1,000+
    Suitability
    More filters
    All 27 Rentals in East Chatham
    Sort by:
    Default
    Don't let other travelers get your favorite East Chatham area vacation rental. You're so close to securing your perfect getaway. Book today.
    East Chatham
    3 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    East Chatham
    3 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    East Chatham
    3 Bedrooms, Sleeps 9Quick View
    Check In Check Out
    Show Prices
    East Chatham
    Studio, Sleeps 12Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
    • Grill
    • Internet Access
    • Air Conditioning
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    East Chatham, New York 12060
    Rental Home - 4 Bathrooms, Sleeps 12
    Make Inquiry
    East Chatham
    Studio, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Hot Tub
    • Washer
    • Sauna
    • Patio
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    East Chatham, New York 12136
    Rental Home - 1 Bathroom, Sleeps 6
    Make Inquiry
    The following rentals are within 10 miles of East Chatham.
    West Stockbridge, MA
    5 of 5 bubbles
    26 Reviews
    5 Bedrooms, Sleeps 12Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    Reviewed January 2, 2017
    This Berkshire Farmhouse worked out great for our 3 family reunion. The house was clean, stocked with plenty of blankets and towels, as well as many other amenities. The owner...
    Excellent of 5 bubbles
    Reviewed May 9, 2016
    Our group of eight adults had a very wonderful experience at Elaine's Berkshire farmhouse. We found it in excellent condition. Full kitchen had everything we needed to create...
    See all reviews
    About this property
    Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16" floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,...
    View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 12
    Make Inquiry
    Richmond, MA
    4.5 of 5 bubbles
    6 Reviews
    3 Bedrooms, Sleeps 6Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Average of 5 bubbles
    Reviewed October 26, 2015
    Better directions to the house would have been helpful. For two nights my daughter and two granddaughters joined us and found the yard and swingset fun. The weather was quite...
    Excellent of 5 bubbles
    Reviewed September 7, 2015
    This house was very comfortable and quiet. We had everything that we needed in the house. The house was clean. The beds were comfortable and cozy. The neighborhood was also...
    See all reviews
    About this property
    Fantastic spot for families and for those looking for a quiet getaway. Come have some summer fun, enjoy the autumn colors or play in the snow. This year round cottage is the perfect spot for those who enjoy outdoor activities. The house is on a private dead end road, has a wonderful lake view...
    View all property information
    Location Information
    Richmond, Berkshires 01254
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    Richmond, MA
    5 of 5 bubbles
    1 Review
    2 Bedrooms, Sleeps 6Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Private Yard
    • Satellite TV
    • Grill
    • Secure Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed June 14, 2016
    My wife and I stayed here for a week in June. The hosts/owners are new to the rental business, but were eager to make sure everything was in order for us. The house is very...
    See all reviews
    About this property
    Beautiful two bedroom house sits just steps from Richmond Pond. Enjoy a day on the water swimming and fishing followed by an evening enjoying the symphony at Tanglewood (ten scenic minutes away). Yoga enthusiasts will love the proximity to Kripalu (again, ten minutes away). Leaf peepers and skiers...
    View all property information
    Location Information
    Richmond, Berkshires 01254
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    Austerlitz
    3 Bedrooms, Sleeps 6Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Washer
    • Parking
    • Shared Yard
    • Internet Access
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 Bedroom 2.5 bathroom recently constructed home sits on 40 wooded, secluded acres in Austerlitz, Columbia County, just 4 miles from the Massachusetts border. It offers stunning views of the Catskills, peace and quite and plenty of nature to watch from the back porch. Chatham, NY is 15 minutes...
    View all property information
    Location Information
    Austerlitz, New York 12017
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    West Stockbridge, MA
    5 of 5 bubbles
    1 Review
    5 Bedrooms, Sleeps 12Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed October 18, 2016
    We had a wonderful time staying at this property. The house is full of charming details - we kept discovering art objects till the time of our departure. The kids had fun using...
    See all reviews
    About this property
    Rent a comfortable 1840 farmhouse with 26 acres in the Berkshire mountains. Walk to the village of West Stockbridge or a short drive to all the Berkshire attractions. Close to the ski resorts of Butternut, Bousquet, Catamount and Jiminy Peak. The house sleeps 10 to 12 people and is fully equipped....
    View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Inquiry
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    Valatie
    4.5 of 5 bubbles
    3 Reviews
    3 Bedrooms, Sleeps 5Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Satellite TV
    • Patio
    • Internet Access
    • DVD Player
    • Grill
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning New Lakefront Home Near Berkshires with Gourmet Kitchen, large expansive views of Kinderhook Lake. All the bells and whistles including a TV in the Master Bathroom and a whole house stereo system. This home is an air conditioned, upscale Craftsman- styled cottage with 75 feet of lakefront...
    View all property information
    Location Information
    Valatie, New York 12184
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 5
    Make Inquiry
    Spencertown
    2 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Patio
    • Satellite TV
    • Internet Access
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Frank Lloyd Wright-inspired retreat is the perfect country escape for city dwellers. Set on 30 private acres with trails for hiking and a lake, this professionally decorated home blends rustic charm with modernity. There are two bedrooms, one with a fireplace, two bathrooms, plus a sleeping...
    View all property information
    Location Information
    Spencertown, New York 12165
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    West Stockbridge, MA
    5 of 5 bubbles
    2 Reviews
    2 Bedrooms, Sleeps 6Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed December 18, 2013
    We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
    See all reviews
    About this property
    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living...
    View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    West Stockbridge, MA
    5 of 5 bubbles
    6 Reviews
    3 Bedrooms, Sleeps 8Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    • Washer
    • Porch
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed August 27, 2016
    We had a wonderful stay in this large, lovely house that contained everything we needed for comfort and convenience. We were impressed with the degree to which details were...
    Excellent of 5 bubbles
    Reviewed November 2, 2014
    Had an outstanding couple of weeks staying here; place was quiet, peaceful and not too far from civilization. All the amenities and space you could wish for and Cassandra and...
    See all reviews
    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private. Visit our web-site aberkshirehome. The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is...
    View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    Nassau
    3 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Washer
    • Patio
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Understated Post and Beam house on a private bluff with views of the Catskills. Elicits calm and pleasure on approach and entry. The house sits on 23 acres of open fields and wooded trails on a road (known locally for its beauty) with ponds and horse farm. The house has cathedral ceilings on both...
    View all property information
    Location Information
    Nassau, New York 12123
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    Canaan
    5 of 5 bubbles
    1 Review
    3 Bedrooms, Sleeps 8Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Grill
    • DVD Player
    • Parking
    • Central Heating
    • Mountain Views
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Mountain Top Custom Built Post + Beam Home Highest Point in Columbia County - Mercer Mountain 2500 Sq Ft Home with Incredible Views and Sunsets Large 1000 Sq Ft Deck - Privacy - 6.25 Acres Hand Cut Beams from Nova Scotia with Stone Throughout Ist Floor Master Suite - 2 Bedrooms on 2nd Floor - Loft...
    View all property information
    Location Information
    Canaan, New York 12060
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    Ghent
    2 Bedrooms, Sleeps 4Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Air Conditioning
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will be enjoying a newly renovated space with Calcutta marble floors throughout. The house features 2 bedrooms at opposite sides of the house to provide more privacy. A luxurious bathroom with a Roman soaking tub and marble mosaics. A totally loaded kitchen and great outdoor space which...
    View all property information
    Location Information
    Ghent, New York 12075
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Austerlitz
    6 Bedrooms, Sleeps 14Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Hot Tub
    • Central Heating
    • Balcony
    • Grill
    • Patio
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The beautiful renovated Georgian Colonial home sits amongst 40 acres of natural beauty. The house overlooks a serene pond and all its beauty with views of natural forrest beyond. The house itself has a oversized chef's eat in kitchen. The Kitchen has all the amenities to host wonderful meals and...
    View all property information
    Location Information
    Austerlitz, New York 12017
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Make Inquiry
    Old Chatham
    5 of 5 bubbles
    1 Review
    1 Bedroom, Sleeps 2Quick View
    other traveler has booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Private Yard
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed September 20, 2016
    We cannot say enough about how wonderful the property and the Owner are. Modern and well appointed, this property is beyond expectations. Private and immaculate, much time and...
    See all reviews
    About this property
    Beautiful suite in a gorgeous county home in the Berkshires. Private entrance and your own courtyard with garden views. Large comfortable bed with plenty of pillows and luxurious spa- style bathroom. Close to Tanglewood, Jacobs Pillow, Kripalu, Great Barrington, and Hudson. Hiking, biking, and...
    View all property information
    Location Information
    Old Chatham, New York 12136
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Ghent
    5 of 5 bubbles
    1 Review
    1 Bedroom, Sleeps 4Quick View
    other travelers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Satellite TV
    • Patio
    • DVD Player
    • Grill
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed August 6, 2013
    This was the perfect location for a base camp from which to explore the Hudson River Valley area. We took in a Tanglewood concert (40-minute drive) and explored the backroads...
    See all reviews
    About this property
    Enjoy a newly renovated and furnished, one bedroom guest cottage, in an enchanting and quiet area. Located behind a stone castle on a 2 1/2 acre park-like property it's a beautiful place to vacation. You also have access to a large 6 person hot tub and all the deck areas.<BR><BR>The bedroom and...
    View all property information
    Location Information
    Ghent, New York 12075
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    Chatham
    4 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Terrace
    • Housekeeping Included
    • Balcony
    • Central Heating
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully renovated 1800s farm house on 100 acres with heated in ground gunnite pool, hiking trails located on a beautiful creek. We also have a guest house with two more bedrooms and a full kitchen by the pool that is perfect for bringing your in-laws or babysitter. The house has a chef's kitchen...
    View all property information
    Location Information
    Chatham, New York 12037
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 6
    Make Inquiry
    Richmond, MA
    3 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Internet Access
    • Washer
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed...
    View all property information
    Location Information
    Richmond, Berkshires 01254
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    Kinderhook
    2 Bedrooms, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Private Yard
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Conveniently located for your next Hudson Valley Wine Tour or Relaxing Hudson Valley Bed and Breakfast Hotel Lodging Get-a-way with an Organic Farm to Table Breakfast! Mile Hill B and B, c.1852, is an original jewel with an interesting history. This is a newly renovated Colonial Farm House; two...
    View all property information
    Location Information
    Kinderhook, New York 12106
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    Old Chatham
    5 of 5 bubbles
    1 Review
    4 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Grill
    • Waterfront
    • Patio
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed November 4, 2015
    This was such a great place for us to stay , it had everything , even went fishing - biking , the house was just perfect , we even had friends over and we had plenty of room...
    See all reviews
    About this property
    'One of a kind' listing.<BR>Gated , 4BR Elegant Colonial Estate on Pristine River/stream in most desirable area in Columbia County.<BR>Set in sleepy upscale Historic Hamlet on Park-like grounds.<BR>Bordered by over 150 acres of fields with Sunset views.<BR>The best Swimming , fantastic Fishing,...
    View all property information
    Location Information
    Old Chatham, New York 12136
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    Canaan
    1 Bedroom, Sleeps 2Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Balcony
    • Air Conditioning
    • Grill
    • Outdoor Dining Area
    • Porch
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A cute cabin in the woods with easy access to a lake a short 500 ft walk down a dirt road. Swimming is available at a private member beach by either canoe or a sort drive to the other end of the the Lake. Convenient to the Berkshires. Tanglewood is a 15 min drive and Jacob's Pillow and Saratoga...
    View all property information
    Location Information
    Canaan, New York 12029
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    West Stockbridge, MA
    2 Bedrooms, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Balcony
    • Central Heating
    • Housekeeping Included
    • Terrace
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recently renovated Victorian farm house on two beautifully landscaped acres with seasonal flower and vegetable gardens, adjoining woods and fields. Ten minutes to Tanglewood, Great Barrington and Stockbridge, and convenient to all other Berkshire attractions. Adjacent to scenic biking and hiking...
    View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    Canaan
    3 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Yard
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Grey House is a relaxing retreat nestled on 7 acres of private, park-like setting. Close to lakes, hikes, cultural activities and skiing. This beautifully furnished property is perfect for accommodating large groups/families, and can sleep 6+. The Space This designer-decorated house with 3...
    View all property information
    Location Information
    Canaan, New York 12029
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    East Chatham Flight and Weather Info
    Airports nearby (1)
    Plan your day of travel
    ALB
    Albany Intl Airport
    27.3 miles from East Chatham
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    52° 29°
    April
    62° 39°
    May
    70° 48°
    June

    Additional East Chatham Info

    View Map
    • Local time: 04:36 PM (EDT)
    List your property
    Owner log in