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Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Chatham Cottages

Rose Cottage
Situated in a forested area, this cabin features a simple design with a flat roof and a front porch with a railing, perfect for outdoor dining and grilling.

Rose Cottage

9.6 out of 10, Exceptional, (5)
"It's so peaceful there. It was lovely."
Rose Cottage
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Enjoy a serene atmosphere with a view of lush greenery from the large window, and dine in style at the set table for two.

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

2.0 star property
9.0 out of 10, Wonderful, (4)
"Cozy, serene and bucolic waterfront hideaway within driving distance of Tanglewood, Shakespeare & Company, Jacob's Pillow and all the wonderful food and cultural Berkshire gems! Julie and Russ were amazing hosts. Great communication and wonderful restaurant and museum suggestions. Definitely planning another long weekend retreat!"
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
Property grounds

Heaven Can't Wait, On Beautiful Kinderhook Lake!!

9.8 out of 10, Exceptional, (83)
"Home our mother's 83rd birthday party cookout at the lake house with a few family members and it was a great day. Everyone loved the house. We enjoyed the stay"
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Surrounded by tall trees, this cozy cabin offers a peaceful retreat in a natural setting.

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

9.0 out of 10, Wonderful, (39)
"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Charming Cottage in Private Lake Community (Pet-Friendly!)
Fully equipped kitchen with refrigerator, microwave, oven, sink, and window.

Charming Cottage in Private Lake Community (Pet-Friendly!)

9.8 out of 10, Exceptional, (30)
"We enjoyed ourselves,relaxed,visited had a very enjoyable bisit"
Charming Cottage in Private Lake Community (Pet-Friendly!)
Charming Cottage in the Heart of Catskill & Pet Friendly
Enjoy outdoor dining at The New York Restaurant with tables and chairs set amidst lush greenery.

Charming Cottage in the Heart of Catskill & Pet Friendly

10.0 out of 10, Exceptional, (14)
"Really enjoyed my stay! Very thoughtful host. "
Charming Cottage in the Heart of Catskill & Pet Friendly
Lake Views & Dock Access - Pittsfield Cottage!
Sit by the lake and enjoy a serene moment with a cup on the dock.

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (4)
"We stayed with family and friends and loved all of the offerings from the dock, fire pit and quiet neighborhood."
Lake Views & Dock Access - Pittsfield Cottage!
4 Mi to Dtwn Catskill: Mtn-view Home
House (4 Bedrooms) | Interior

4 Mi to Dtwn Catskill: Mtn-view Home

3.0 star property
4 Mi to Dtwn Catskill: Mtn-view Home
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
Relax in this cabin with a bed, large window offering a view of the surrounding water and greenery.

Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake

10.0 out of 10, Exceptional, (7)
"Very clean, cute house right on the lake. We enjoyed our time there. "
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
The Blue Elm - A Historic Berkshire Cottage
Enjoy outdoor dining or relaxation on the porch, surrounded by a serene lawn and mature trees.

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (7)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
The price is CA $276
CA $570 total
includes taxes & fees
Aug 4 - Aug 5
The Blue Elm - A Historic Berkshire Cottage
Beachwood Cottage
Cozy interior with a brick fireplace, wooden ceiling, and a panelled wall.

Beachwood Cottage

10.0 out of 10, Exceptional, (4)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage
Quiet rustic cottage with shared lake access
Enjoy cooking in this well-equipped kitchen with a central island, dishwasher, stove, and refrigerator.

Quiet rustic cottage with shared lake access

10.0 out of 10, Exceptional, (109)
"Lovely lake house at the end of a long private road, perfect for a quiet getaway, close to all kinds of hiking and other natural attractions. Our hosts were super friendly and responsive. Highly recommended."
Quiet rustic cottage with shared lake access
Cozy cottage with pool, walking distance to lake
Relax by the pool surrounded by lush greenery and comfortable outdoor furniture.

Cozy cottage with pool, walking distance to lake

10.0 out of 10, Exceptional, (15)
"The house was very convenient to anywhere we wanted to go. We even had 5 deer welcome us the first night. House was very comfortable and we loved it."
Cozy cottage with pool, walking distance to lake
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Relax in a peaceful room with large windows overlooking the surrounding trees, a perfect spot for socializing and taking in the views.

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.2 out of 10, Wonderful, (12)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Grandparent’s Cottage 250 steps to the lake
Sun loungers, beach towels

Grandparent’s Cottage 250 steps to the lake

Grandparent’s Cottage 250 steps to the lake
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Relax in the inviting porch area with Adirondack chairs and a cozy table.

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

10.0 out of 10, Exceptional, (4)
"A lovely cabin centrally located in the Berkshires! Had everything we needed for our stay, including air conditioning during a heat wave! "
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Berkshires farm, 30+ guests, 50 acres
Situated on a grassy area, this charming home features a traditional two-story design with a prominent porch and a small attached structure.

Berkshires farm, 30+ guests, 50 acres

2.0 star property
The price is CA $1,879
CA $2,934 total
includes taxes & fees
Sep 1 - Sep 2
Berkshires farm, 30+ guests, 50 acres
Private Hot Tub: Hudson Valley Cabin Retreat!
House (3 Bedrooms) | Interior

Private Hot Tub: Hudson Valley Cabin Retreat!

3.0 star property
Private Hot Tub: Hudson Valley Cabin Retreat!
Spacious Historic Home in the Berkshires!
House (5 Bedrooms) | Interior

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Charming loft cottage in tranquil Germantown with WiFi, AC
Welcome to a charming home with a beautifully maintained front yard and a welcoming entrance.

Charming loft cottage in tranquil Germantown with WiFi, AC

10.0 out of 10, Exceptional, (4)
"Sparkling clean, lovely and cozy hideaway. We only stayed overnight, but the kitchenette would be perfect for a longer stay. Hope we can come back sometime and stay longer."
The price is CA $150
CA $283 total
includes taxes & fees
Aug 4 - Aug 5
Charming loft cottage in tranquil Germantown with WiFi, AC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chatham Hotel Reviews

Postcard Cabins Eastern Catskills

Postcard Cabins Eastern Catskills

10/10 Excellent
"The best "
Carlos 1-night trip
Posted 12 hours ago
Postcard Cabins Eastern Catskills