Holiday Homes in Old Chatham

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Old Chatham holiday homes

A spacious living room with a dining area, a kitchen, and a large window.

1. 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 AU$319
includes taxes & fees
18 Nov - 19 Nov
1800s Carriage house in Berkshires / Hudson Valley
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

2. 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 AU$295
includes taxes & fees
18 Nov - 19 Nov
NEW RENO - Chalet-style farm loft near Tanglewood
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.
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, (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 AU$479
includes taxes & fees
22 Nov - 23 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, (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 AU$675
includes taxes & fees
18 Nov - 19 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.
The price is AU$951
includes taxes & fees
18 Nov - 19 Nov
Luxury Barn Near Hudson With New Private Sauna
A wooden deck with a staircase leading to a covered porch area.

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 AU$197
includes taxes & fees
16 Nov - 17 Nov
All the comforts of home
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

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 AU$830
includes taxes & fees
3 Dec - 4 Dec
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A hotel lobby with a leather sofa, a coffee table, and a dining area with tables and chairs.

9. 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 AU$187
includes taxes & fees
16 Nov - 17 Nov
Albany Retreat- Free Breakfast & Parking Included
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

10. 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 AU$808
includes taxes & fees
9 Dec - 10 Dec
NEW RENO Historic Creamery in Berkshires w/hot tub
A cozy room with a large window overlooking a lake, furnished with wicker chairs, a sofa, and a coffee table.

11. Lakefront Retreat Hot Tub, Dock, Kayaks, & Firepit

Lakefront Retreat Hot Tub, Dock, Kayaks, & Firepit
Averill Park
10.0 out of 10, Exceptional, (1 review)
""Love it! I've booked a lot of houses over the years, and this one is at the top of the list. Everything in the description and photos was spot on. The owner communicated well and responded promptly to any questions. It was the perfect fall getaway, and we look forward to coming back in the summer!""
United States
Mark R.
The price is AU$894
includes taxes & fees
16 Nov - 17 Nov
Lakefront Retreat Hot Tub, Dock, Kayaks, & Firepit
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 AU$709
includes taxes & fees
17 Nov - 18 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, (10 reviews)
"Perfect accommodations. Every detail was provided!"
United States
Mary R.
The price is AU$526
includes taxes & fees
14 Dec - 15 Dec
Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking
A bedroom with two beds, a ceiling fan, a dresser, and a television.

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 AU$494
includes taxes & fees
22 Nov - 23 Nov
Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking
A living room with a fireplace, a television mounted above it, and a sofa.

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 AU$417
includes taxes & fees
16 Nov - 17 Nov
Downtown 3BR duplex full kitchen parking off i-787
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

16. 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 AU$443
includes taxes & fees
19 Nov - 20 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.
A wooden deck with a wicker sofa, a hammock, and a grill.

17. 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 AU$811
includes taxes & fees
17 Nov - 18 Nov
Modern Family Home · Walk to Lake · Firepit
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

18. 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 AU$1,601
includes taxes & fees
17 Nov - 18 Nov
Hancock Village Inn Near Jiminy Peak
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

19. 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 AU$951
includes taxes & fees
30 Nov - 1 Dec
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.

20. 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 AU$1,076
includes taxes & fees
16 Nov - 17 Nov
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
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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Learn more about Old Chatham

Tucked in the Hudson Valley, this historic hamlet offers peaceful countryside walks and the charming Old Chatham Country Store for local provisions. Nearby Shaker Museum preserves artefacts from America's oldest Shaker settlement, while Chatham's Main Street features independent shops and farm-to-table dining.

See all hotels in Old Chatham
A brick building with a green dome and columns, labeled "TRACY MEMORIAL VILLAGE HALL".

Top reviews in Old Chatham

Two Adirondack chairs facing a river with a forested hill in the background.
The Yankee Inn

The Yankee Inn

The Yankee Inn
Lenox

10/10 Excellent

A convenient location. Excellent well appointed and clean room. An excellent breakfast provided. Would stay again.
Australia
Lawrence
Reviewed April 16, 2026
The Yankee Inn