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
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Old Chatham vacation homes

Coffee/tea maker, fridge, microwave, oven

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

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is AED 320
AED 835 total
includes taxes & fees
8 Sep - 9 Sep
NEW RENO - Chalet-style farm loft near Tanglewood
Property grounds

2. 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, (13 reviews)
"This property is really nice. House is beautiful and the man cave is a nice addition. Wish we were there long enough to use it."
United States
Jen R.
The price is AED 735
AED 1,263 total
includes taxes & fees
20 Sep - 21 Sep
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Exterior detail

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 1,466
AED 2,929 total
includes taxes & fees
2 Sep - 3 Sep
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
TV, DVD player, books, video library

4. 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 831 total
includes taxes & fees
14 Sep - 15 Sep
1800s Carriage house in Berkshires / Hudson Valley
Coffee/tea maker, fridge, microwave, stovetop

5. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is AED 646
AED 2,087 total
includes taxes & fees
2 Sep - 3 Sep
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Exterior

6. 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 981
AED 2,032 total
includes taxes & fees
9 Sep - 10 Sep
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Property grounds

7. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is AED 390
AED 519 total
includes taxes & fees
3 Sep - 4 Sep
All the comforts of home
Outdoor dining

8. 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, (7 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is AED 852
AED 1,928 total
includes taxes & fees
15 Sep - 16 Sep
NEW RENO Historic Creamery in Berkshires w/hot tub
Terrace/patio

9. 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)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
United States
SteveS
The price is AED 1,068
AED 1,817 total
includes taxes & fees
9 Sep - 10 Sep
Treat yourself at the stunning June Farms Wellness Huts!
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is AED 643
AED 1,173 total
includes taxes & fees
3 Sep - 4 Sep
Sweet Cozy Victorian in Housatonic. Close to everything.
Interior

11. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AED 744
AED 1,163 total
includes taxes & fees
8 Sep - 9 Sep
Cozy Riverside Berkshires Retreat
Pool

12. 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, (9 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 1,047
AED 1,345 total
includes taxes & fees
2 Sep - 3 Sep
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Interior

13. 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 165
AED 456 total
includes taxes & fees
2 Sep - 3 Sep
Albany Retreat- Free Breakfast & Parking Included
Smart TV

14. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.6 out of 10, Exceptional, (7 reviews)
The price is AED 645
AED 1,479 total
includes taxes & fees
14 Sep - 15 Sep
stylish Berkshires Retreat
Interior

15. 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, (6 reviews)
"The house was nicely setup and clean. The location was very central to where we needed to be. The host was very responsive. "
United States
Elizabeth P.
The price is AED 577
AED 1,440 total
includes taxes & fees
8 Sep - 9 Sep
Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking
Coffee/tea maker, fridge, microwave, oven

16. 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 2,801 total
includes taxes & fees
7 Sep - 8 Sep
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Interior

17. Cozy 1 bedroom apt! Prime location! King & Full bed! Sleeps 4! 2 smart TVs!

Cozy 1 bedroom apt! Prime location! King & Full bed! Sleeps 4! 2 smart TVs!
New Scotland
The price is AED 621
AED 1,401 total
includes taxes & fees
2 Sep - 3 Sep
Cozy 1 bedroom apt! Prime location! King & Full bed! Sleeps 4! 2 smart TVs!
Property grounds

18. Larkspire I Sleepy Hollow Lake I Beach & Firepit

Larkspire I Sleepy Hollow Lake I Beach & Firepit
Athens
The price is AED 929
AED 1,964 total
includes taxes & fees
15 Sep - 16 Sep
Larkspire I Sleepy Hollow Lake I Beach & Firepit
Terrace/patio

19. “The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany

“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany
Pine Hills
9.6 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay at this property and will rent again when in the area. The owners were very responsive and great to work with. The apt was beautiful and immaculate. We enjoyed our stay very much. The only area that was perfect was the outside stairs to the front door— uneven, steep, etc. We had older guest with us and this was concerning. But we managed. Thanks again for a great stay"
United States
Melissa A.
The price is AED 731
AED 1,698 total
includes taxes & fees
13 Sep - 14 Sep
“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Good stay but I'd really like them to seriously increase the water pressure for the showers and install better and NEW shower heads. Taking a shower is a freaking chore and takes forever with the the current situation. Also the jacuzzi tubs are just plain unusable in the deluxe units. The water jets are uncontrollable and varied in pressure and just shoot water literally ALL THROUGHOUT THE BATHROOM AND INTO ADJACENT ROOMS. Sooooo, increase the water pressure for the showers. Decrease the pressure in the tubs."
Stephen 5-night trip
Posted less than an hour ago
Vacation Village in the Berkshires