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Our top choices for Old Chatham holiday homes

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 HK$549
HK$1,543 total
includes taxes & fees
9 Nov - 10 Nov
NEW RENO - Chalet-style farm loft near Tanglewood

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 HK$1,968
HK$4,504 total
includes taxes & fees
16 Nov - 17 Nov
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

3. 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 HK$666
HK$1,669 total
includes taxes & fees
9 Nov - 10 Nov
1800s Carriage house in Berkshires / Hudson Valley

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, (17 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 HK$1,568
HK$2,564 total
includes taxes & fees
9 Nov - 10 Nov
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

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 HK$1,192
HK$3,101 total
includes taxes & fees
9 Nov - 10 Nov
1789 Shaker Farmhouse in Berkshires/Hudson Valley

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 HK$3,140
HK$5,255 total
includes taxes & fees
9 Nov - 10 Nov
Luxury Barn Near Hudson With New Private Sauna

7. 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 HK$833
HK$1,038 total
includes taxes & fees
9 Nov - 10 Nov
All the comforts of home

8. 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 HK$1,591
HK$4,351 total
includes taxes & fees
9 Nov - 10 Nov
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

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)
"It was a great stay! Centrally located in the Berkshire, very comfortable beds, amazing amenities!"
United States
Molly K.
The price is HK$2,250
HK$4,317 total
includes taxes & fees
9 Dec - 10 Dec
NEW RENO Historic Creamery in Berkshires w/hot tub

10. 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 HK$445
HK$1,005 total
includes taxes & fees
17 Nov - 18 Nov
Albany Retreat- Free Breakfast & Parking Included

11. 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, (9 reviews)
"Perfect accommodations. Every detail was provided!"
United States
Mary R.
The price is HK$1,145
HK$2,794 total
includes taxes & fees
22 Nov - 23 Nov
Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking

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 HK$2,278
HK$4,190 total
includes taxes & fees
11 Nov - 12 Nov
Treat yourself at the stunning June Farms Wellness Huts!

13. 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 HK$2,038
HK$4,355 total
includes taxes & fees
9 Nov - 10 Nov
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

14. 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 traveller
The price is HK$1,874
HK$2,642 total
includes taxes & fees
22 Nov - 23 Nov
Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking

15. 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 HK$1,268
HK$2,137 total
includes taxes & fees
30 Nov - 1 Dec
Downtown 3BR duplex full kitchen parking off i-787

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 HK$3,105
HK$5,637 total
includes taxes & fees
18 Nov - 19 Nov
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

17. 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 HK$1,317
HK$2,312 total
includes taxes & fees
9 Nov - 10 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.

18. 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 HK$2,971
HK$5,175 total
includes taxes & fees
16 Nov - 17 Nov
Secluded Family Home in Serene Stockbridge Woods

19. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (12 reviews)
"Host was proactive in communication and answer each and every question."
United States
Amit
The price is HK$1,262
HK$4,043 total
includes taxes & fees
9 Nov - 10 Nov
Comfortable Berkshires retreat on mtn resort, SISO

20. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is HK$4,849
HK$8,452 total
includes taxes & fees
9 Nov - 10 Nov
Hancock Village Inn Near Jiminy Peak
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

Find out more about Old Chatham

Old Chatham Vacation Homes information

Number of reviews
177
Accommodation
434 Vacation Homes
Lowest Price
HK$1,005
Highest Price
HK$8,452

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