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Vacation rentals in East Chatham

Vacation rentals in East Chatham

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in East Chatham

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Charming Eyebrow Colonial    North Chatham, NY
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bath
    Charming Eyebrow Colonial North Chatham, NY

    Hike, bike, explore, experience. Entire 2nd floor guest suite with king size bed and private bath including shower. Full breakfast served overlooking peaceful farmlands and gardens. A special place set off from the main road. Convenient to New York State Thruway 90, 87, Taconic Parkway, Albany, Boston, the Berkshires, New England and Niagara Falls.

    What guests are saying:

    “We had an amazing weekend at Susan’s. Our goal for the weekend was to escape the city, explore local fare, and give our pup much needed green space. Susan’s place delivered on all of these. The space was great — the bed was extremely comfortable, it felt very private, and the house in itself was very dog friendly. Susan made us an amazing breakfast both mornings of our stay, and had a great system of playing music at an agreed upon time to let us know she was in the downstairs space. Outside of making breakfast for us, she left the bedroom, kitchen, and living area for our private use. The location was also exactly what we were looking for. We had a great time exploring the local towns, hiking the conservatory, visiting the Chatham Brewery, and listening to live music late night in Valatie. Susan’s place is on an incredible piece of land, and our mini goldendoodle, Charlie, loved exploring. Plus, Susan and Charlie hit it off and she was kind enough to spend some time with her while we explored. Susan’s an amazing pup sitter. Charlie LOVED her. We had an amazing weekend at Susan’s and would 100% recommend her to anyone looking for a nice, quiet weekend away from the city!”

  • Windswept Acres In the Berkshires~Canaan, New York
    SUPERHOSTEntire house · 4 guests · 3 beds · 1 bath
    Windswept Acres In the Berkshires~Canaan, New York

    Welcome to Windswept Acres located just 11 miles to Tanglewood Summer Music Center! This property is a 12 acre pastural mountain top setting in the Berkshires! 3 bedrooms, one bathroom, fully equipped kitchen with new stainless steel appliances. The dining room houses a farm table to accommodate 6. 2 living rooms, one with a cozy pellet stove for added warmth on those chilly Fall/Winter evenings. Backyard private deck with hot tub (open all year) for relaxing while watching the sun set.

    What guests are saying:

    “Deborah's home was a lovely oasis during a stressful time! From every window, there are lovely views of hills and ridges. The birdhouses means that there are so many beautiful birds around. Just being in the house was relaxing enough, but the hot tub made it that much better. We could relax for hours under the stars or watching the sunset. The house itself is spacious and clean, and had everything we needed for our stay. The location was very convenient, close to many nice conservation areas and parks for walks and hikes. Deborah herself was communicative, friendly, and accommodating. We would recommend to anyone and hope to be back soon!”

  • Berkshire Country Summer Rental: July - Labor Day
    SUPERHOSTEntire apartment · 2 guests · 1 bed · 1 bath
    Berkshire Country Summer Rental: July - Labor Day

    Solitude, the Berkshires, Columbia County and more are yours in this newly renovated (living room furnishings are on order) sun soaked country efficiency apartment Private entrance via gardened back yard. Magical gardens, bird symphonies, country road strolls, swim in the private community lake, walk to the tennis courts. Hike up the fire tower for a 360 view of the Berkshire, Catskill and Green Mountains. Minutes to Chatham, Hudson, Lenox, Stockbridge, Great Barrington. July-Labor Day rental.

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Popular amenities for East Chatham vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in East Chatham

The Inn at Chatham - Romantic getaway
SUPERHOSTEntire guest suite
The Inn at Chatham - Romantic getaway
Price:$128 CAD/night
Star Gazer Farm
SUPERHOSTEntire guest suite
Star Gazer Farm
Price:$161 CAD/night
Retrograss Farm Apartment
SUPERHOSTFarm stay
Retrograss Farm Apartment
Price:$158 CAD/night
Beautiful Lake Front Cabin
Entire house
Beautiful Lake Front Cabin
Price:$336 CAD/night
Comfortable Country Two Bedroom Apartment
SUPERHOSTEntire guest suite
Comfortable Country Two Bedroom Apartment
Price:$114 CAD/night
Cozy Suite with huge bar and stone fireplace!
Entire apartment
Cozy Suite with huge bar and stone fireplace!
Price:$60 CAD/night
Airy cottage with meadow views in The Berkshires
SUPERHOSTEntire guesthouse
Airy cottage with meadow views in The Berkshires
Price:$195 CAD/night
The old sawmill from 1771
SUPERHOSTEntire house
The old sawmill from 1771
Price:$160 CAD/night
Sweet Hamlet Apartment
SUPERHOSTEntire apartment
Sweet Hamlet Apartment
Price:$154 CAD/night
Shadowbrook Farm Stay
SUPERHOSTFarm stay
Shadowbrook Farm Stay
Price:$336 CAD/night
Arnold Farmhouse (second room) (Italianate)
SUPERHOSTPrivate room
Arnold Farmhouse (second room) (Italianate)
Price:$96 CAD/night
Queen Suite on Horse Farm
SUPERHOSTPrivate room
Queen Suite on Horse Farm
Price:$114 CAD/night
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