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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Chatham vacation homes

A camping setup with a metal chair and a table by a river in a forest.

1. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (18 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is ￥31,942
￥52,053 total
includes taxes & fees
Nov 15 - Nov 16
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A modern building with a wooden deck and a door.

2. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is ￥40,087
￥91,763 total
includes taxes & fees
Nov 30 - Dec 1
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A wooden deck with a staircase leading to a covered porch area.

3. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is ￥16,961
￥21,144 total
includes taxes & fees
Nov 17 - Nov 18
All the comforts of home
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

4. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.8 out of 10, Excellent, (8 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is ￥11,180
￥30,895 total
includes taxes & fees
Nov 16 - Nov 17
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

5. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is ￥13,575
￥33,290 total
includes taxes & fees
Nov 15 - Nov 16
1800s Carriage house in Berkshires / Hudson Valley
A cozy living room with a sofa, a fireplace, and large windows.

6. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is ￥59,732
￥99,992 total
includes taxes & fees
Nov 18 - Nov 19
Luxury Barn Near Hudson With New Private Sauna
A white two-story house with a porch, surrounded by trees and a hill.

7. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (6 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is ￥26,033
￥65,117 total
includes taxes & fees
Nov 16 - Nov 17
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A modern kitchen with a central island, built-in appliances, and a dining area with a round table.

8. 2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Stottville
The price is ￥63,316
￥115,862 total
includes taxes & fees
Nov 16 - Nov 17
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

9. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is ￥28,109
￥48,702 total
includes taxes & fees
Nov 18 - Nov 19
Sweet Cozy Victorian in Housatonic. Close to everything.
A wooden deck with a wicker sofa, a hammock, and a grill.

10. Modern Family Home · Walk to Lake · Firepit

Modern Family Home · Walk to Lake · Firepit
Athens
10.0 out of 10, Exceptional, (2 reviews)
"Lovely home with reasonable accessibility. Host was very responsive. Clean and quiet. Beautiful scenery."
United States
Kellie H.
The price is ￥43,848
￥88,925 total
includes taxes & fees
Nov 17 - Nov 18
Modern Family Home · Walk to Lake · Firepit
A wooden cabin with a door open to a sandy beach, a sign reading "Ditch House," and a view of a lake and forest in the background.

11. Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren

Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
Hudson
10.0 out of 10, Exceptional, (7 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
United States
Brittaney O.
The price is ￥34,497
￥71,647 total
includes taxes & fees
Dec 2 - Dec 3
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
A modern living space with a kitchen area, a dining table, and a sofa.

12. Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is ￥22,182
￥42,579 total
includes taxes & fees
Nov 17 - Nov 18
Cabin Oasis near Town
A kitchen with a central island, bar stools, and pendant lighting.

13. Cozy Catskill Escape

Cozy Catskill Escape
Catskill
10.0 out of 10, Exceptional, (2 reviews)
"Very accommodating host. Great with last minute visits."
United States
Kevin P.
The price is ￥19,520
￥40,171 total
includes taxes & fees
Nov 30 - Dec 1
Cozy Catskill Escape
A wooden deck leading to a cabin with a window and a door, surrounded by trees.

14. Modern cabin retreat

Modern cabin retreat
Catskill
The price is ￥22,182
￥40,804 total
includes taxes & fees
Nov 17 - Nov 18
Modern cabin retreat
A dining area with a wooden table, chairs, and a ceiling fan.

15. A Cozy Berkshire Escape l Close to the Slopes

A Cozy Berkshire Escape l Close to the Slopes
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is ￥32,341
￥47,900 total
includes taxes & fees
Nov 16 - Nov 17
A Cozy Berkshire Escape l Close to the Slopes
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

16. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is ￥54,477
￥95,104 total
includes taxes & fees
Nov 16 - Nov 17
Secluded Family Home in Serene Stockbridge Woods
A cabin with a large deck, multiple windows, and a fire pit.

17. Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (16 reviews)
"The perfect stay in the Catskills! Everything looked just like the pictures. Clean, easy access to restaurants close by, and Daniel was very easy to communicate with. Highly recommend!"
United States
Amanda
The price is ￥27,630
￥54,851 total
includes taxes & fees
Nov 30 - Dec 1
Modern Luxurious Cabin, Catskills - The Tiny Nook
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

18. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.2 out of 10, Wonderful, (10 reviews)
"Great property and the host was extremely responsive and helpful."
United States
Robbie S.
The price is ￥32,421
￥91,475 total
includes taxes & fees
Nov 15 - Nov 16
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A modern living room with a sectional sofa, wooden beams, a large window, and a view of the outdoors.

19. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires
West Stockbridge
The price is ￥123,775
￥199,554 total
includes taxes & fees
Dec 1 - Dec 2
Beautiful and Private Home Centrally Located in the Berkshires
A modern interior with a loft-style ceiling, a grey sofa, a wooden coffee table, and a kitchen area with a large TV.

20. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is ￥60,690
￥98,203 total
includes taxes & fees
Nov 15 - Nov 16
Fantastic 2-bedroom house with AC in quaint Hillsdale.
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"The staff were super kind and helpful, however there were some concerns. The indoor pool was closed because there were too many pool chemicals in it, which was tough since that was a primary reason for choosing this property. This meant that the families with children were relegated to the hot tub and pool table areas because the arcade area costs money to play. The staff were kind, but the lack of swimming pool and the abundance of bored children arouns changed the atmosphere. "Too many chemicals" in the pool seems like an avoidable problem. The room was lovely, but we had to take out our own trash and wash our own dishes which wasn't quite "vacation vibes" since this was listed as a hotel. Loved the gas fireplace, but it does run on by using a dial on the wall that makes a ticking sound constantly. The walls were super thin, so I could see where that would be a challenge during busy season. Honestly, I feel like the whole property would feel kind of feral during busy season with so many "first come, first served" elements, but the mountain views were gorgeous and the staff were very very kind and helpful. Also, the room was beautifully clean and cozy, which is always a nice feeling."
Johanna 1-night trip
Posted 3 hours ago
Vacation Village in the Berkshires

Find out more about Chatham

Chatham Vacation Homes information

Number of reviews
155
Accommodation
502 Vacation Homes
Lowest Price
￥21,144
Highest Price
￥115,862