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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.

  • 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.

  • 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!”

  • The Inn at Chatham - Romantic getaway
    SUPERHOSTEntire guest suite · 3 guests · 1 bed · 1 bath
    The Inn at Chatham - Romantic getaway

    Beautiful , private 1-bedroom suite in a gracious 1820s Chatham home in the center of Chatham Village, right off of the Main Street- the perfect getaway!Your own entrance to a federal-inspired living space with a convertible day bed, and a huge Edwardian bedroom with high ceilings and large windows. Easy walking to Village shops, cinema, brewery and restaurants - close to Hudson and Berkshires, hiking, skiing, museums, Tanglewood, etc. Get away from it all while being close to amenities.

    What guests are saying:

    “So happy to find Jon's apartment and would absolutely book it again. It's very thoughtfully decorated and appropriate to the feeling you want when spending a weekend in a country village. It is clean, warm, and has a comfortable bed. Perfect location right in the village, very walkable, with great cafes right around the corner. I didn't meet Jon in person, but he was responsive, kind, and helpful when I did reach out.”

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for East Chatham vacation rentals

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

Other great vacation rentals in East Chatham

Arnold Farmhouse (second room) (Italianate)
SUPERHOSTPrivate room
Arnold Farmhouse (second room) (Italianate)
Price:€63 / night
Cozy Suite with huge bar and stone fireplace!
Entire apartment
Cozy Suite with huge bar and stone fireplace!
Price:€40 / night
Queen Suite on Horse Farm
SUPERHOSTPrivate room
Queen Suite on Horse Farm
Price:€71 / night
Charming Ghent Getaway, minutes from Hudson!
Entire apartment
Charming Ghent Getaway, minutes from Hudson!
Price:€67 / night
Equestrian retreat
SUPERHOSTPrivate room
Equestrian retreat
Price:€84 / night
Comfortable Camping in the Woods
SUPERHOSTCampsite
Comfortable Camping in the Woods
Price:€52 / night
Beautiful Lake Front Cabin
Entire house
Beautiful Lake Front Cabin
Price:€222 / night
Spacious Apartment
SUPERHOSTEntire apartment
Spacious Apartment
Price:€69 / night
Sweet Hamlet Apartment
SUPERHOSTEntire apartment
Sweet Hamlet Apartment
Price:€102 / night
Private, luxurious Berkshire loft/cabin
SUPERHOSTEntire loft
Private, luxurious Berkshire loft/cabin
Price:€173 / night
Retrograss Farm Apartment
SUPERHOSTFarm stay
Retrograss Farm Apartment
Price:€105 / night
Haddock Hill House
Private room
Haddock Hill House
Price:€128 / night
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