A brick building with a green dome and columns, labeled "TRACY MEMORIAL VILLAGE HALL".

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Old Chatham vacation homes

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

1. 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 AED 257
AED 719 total
includes taxes & fees
3 Nov - 4 Nov
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

2. 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 AED 312
AED 778 total
includes taxes & fees
8 Nov - 9 Nov
1800s Carriage house in Berkshires / Hudson Valley
A modern building with a wooden deck and a door.

3. 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 AED 988
AED 2,189 total
includes taxes & fees
16 Nov - 17 Nov
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A camping setup with a metal chair and a table by a river in a forest.

4. 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, (16 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 AED 735
AED 1,197 total
includes taxes & fees
16 Nov - 17 Nov
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A white two-story house with a porch, surrounded by trees and a hill.

5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 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 AED 617
AED 1,508 total
includes taxes & fees
3 Nov - 4 Nov
1789 Shaker Farmhouse 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.
Luxury Barn Near Hudson With New Private Sauna
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

7. 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)
"A lovely house! Very convenient for a Tanglewood weekend."
United States
Robert B.
The price is AED 746
AED 2,087 total
includes taxes & fees
3 Nov - 4 Nov
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A wooden deck with a staircase leading to a covered porch area.

8. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"No frills, very clean and peaceful, beautiful setting"
United States
Lori M.
The price is AED 390
AED 486 total
includes taxes & fees
4 Nov - 5 Nov
All the comforts of home
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

9. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (8 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is AED 1,087
AED 1,973 total
includes taxes & fees
9 Nov - 10 Nov
NEW RENO Historic Creamery in Berkshires w/hot tub
A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

10. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay in the Berkshires! The house was lovely, very clean, and such a cozy place to spend a fall weekend. The overlook was absolutely stunning, especially with all the beautiful fall foliage! We loved that the property felt peaceful and tucked away while still being a short drive to Lenox, nearby towns, and plenty of great hiking trails. The host was so kind and always quick to respond, which made everything easy from start to finish. We really enjoyed our stay and would...
United States
Delaney M.
Ellie’s Overlook, best view in the Berkshires!
A hotel lobby with a leather sofa, a coffee table, and a dining area with tables and chairs.

11. Albany Retreat- Free Breakfast & Parking Included

Albany Retreat- Free Breakfast & Parking Included
West End
5.8 out of 10, (8 reviews)
"Best stay yet"
United States
Jacob M.
The price is AED 202
AED 464 total
includes taxes & fees
4 Nov - 5 Nov
Albany Retreat- Free Breakfast & Parking Included
A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery.

12. Treat yourself at the stunning June Farms Wellness Huts!

Treat yourself at the stunning June Farms Wellness Huts!
West Sand Lake
10.0 out of 10, Exceptional, (8 reviews)
"Loved the wellness hut. Our sauna didnt work however the room was spacious and comfy. The staff is very attentive and we also enjoyed the soup stroll. Would def recommend."
United States
Lauren C.
The price is AED 952
AED 1,819 total
includes taxes & fees
3 Nov - 4 Nov
Treat yourself at the stunning June Farms Wellness Huts!
A modern kitchen with white cabinets, a wooden countertop, and a large TV mounted on the wall.

13. Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking

Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking
Pine Hills
9.8 out of 10, Exceptional, (8 reviews)
"Perfect accommodations. Every detail was provided!"
United States
Mary R.
The price is AED 551
AED 1,325 total
includes taxes & fees
22 Nov - 23 Nov
Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking
A couple in a hot tub with a natural landscape in the background.

14. Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Hudson
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful house and wonderful host. I very much hope we get to stay again in the future. "
United States
Jeffrey D.
The price is AED 955
AED 2,040 total
includes taxes & fees
22 Nov - 23 Nov
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

15. 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 AED 735
AED 1,227 total
includes taxes & fees
16 Nov - 17 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.
A room with a large window, two sofas, and a small table.

16. Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
Richmond
The price is AED 3,292
AED 4,595 total
includes taxes & fees
13 Nov - 14 Nov
Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

17. 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 AED 1,253
AED 2,257 total
includes taxes & fees
3 Nov - 4 Nov
Secluded Family Home in Serene Stockbridge Woods
A modern kitchen with a central island, built-in appliances, and a dining area with a round table.

18. 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 AED 1,455
AED 2,641 total
includes taxes & fees
10 Nov - 11 Nov
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
A living room with a fireplace, a television mounted above it, and a sofa.

19. Downtown 3BR duplex full kitchen parking off i-787

Downtown 3BR duplex full kitchen parking off i-787
Arbor Hill
10.0 out of 10, Exceptional, (6 reviews)
"My group of 7 plus myself really enjoyed staying at this house. Ideal for groups with multiple couples, but my friends and I made do with the beds. We really appreciated the attentive host and daily fresh bread, highly recommend staying here if it works for your budget and group."
United States
Francesca L.
The price is AED 513
AED 901 total
includes taxes & fees
3 Nov - 4 Nov
Downtown 3BR duplex full kitchen parking off i-787
A bedroom with two beds, a ceiling fan, a dresser, and a television.

20. Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking

Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking
Albany
8.0 out of 10, Very good, (1 review)
"Overall nice stay "
United States
Anonymous traveler
The price is AED 878
AED 1,238 total
includes taxes & fees
22 Nov - 23 Nov
Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking
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 Old Chatham Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"We had a great stay. The lobby is beautiful- very warm and inviting. Don’t let the motel style fool you. The staff was very welcoming! Room was very spacious. We enjoyed sitting at the fire pit on a chilly fall night. Only suggestion would be softer pillows."
Merry 2-night trip
Posted 6 hours ago
Berkshires Untold