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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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
8.6 out of 10, Excellent, (7 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 ￥14,054
￥36,376 total
includes taxes & fees
Nov 2 - Nov 3
NEW RENO - Chalet-style farm loft near Tanglewood
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.
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A spacious living room with a dining area, a kitchen, and a large window.

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 ￥13,738
￥35,883 total
includes taxes & fees
Nov 2 - Nov 3
1800s Carriage house in Berkshires / Hudson Valley
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, (15 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 ￥31,570
￥53,922 total
includes taxes & fees
Oct 7 - Oct 8
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 ￥32,044
￥74,916 total
includes taxes & fees
Oct 7 - Oct 8
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A spacious room with a wooden ceiling, large windows, and a chandelier.

6. Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is ￥67,086
￥116,329 total
includes taxes & fees
Oct 7 - Oct 8
Luxury Barn Retreat — All-Season Escape Awaits!
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
9.8 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 ￥27,782
￥89,184 total
includes taxes & fees
Oct 7 - Oct 8
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)
"Great location and super welcoming "
United States
Julie B.
The price is ￥16,764
￥22,312 total
includes taxes & fees
Oct 13 - Oct 14
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 ￥43,882
￥90,454 total
includes taxes & fees
Oct 27 - Oct 28
NEW RENO Historic Creamery in Berkshires w/hot tub
A hotel lobby with a leather sofa, a coffee table, and a dining area with tables and chairs.

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 ￥8,950
￥21,600 total
includes taxes & fees
Oct 13 - Oct 14
Albany Retreat- Free Breakfast & Parking Included
A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

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

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is ￥49,723
￥109,094 total
includes taxes & fees
Oct 17 - Oct 18
Ellie’s Overlook, best view in the Berkshires!
A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery and trees.

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)
"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 ￥43,472
￥75,411 total
includes taxes & fees
Nov 3 - Nov 4
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)
"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 ￥26,677
￥62,395 total
includes taxes & fees
Oct 18 - Oct 19
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, (10 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 ￥41,041
￥92,639 total
includes taxes & fees
Oct 28 - Oct 29
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
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.

15. 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 ￥35,056
￥74,944 total
includes taxes & fees
Oct 14 - Oct 15
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
Pool

16. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is ￥25,414
￥85,632 total
includes taxes & fees
Oct 7 - Oct 8
Comfortable Berkshires retreat on mtn resort, SISO
A living room with a sectional sofa, a fluffy throw blanket, and a radiator.

17. Classic Albany Charm – Fully Furnished

Classic Albany Charm – Fully Furnished
Center Square
The price is ￥28,424
￥54,403 total
includes taxes & fees
Oct 17 - Oct 18
Classic Albany Charm – Fully Furnished
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 ￥69,480
￥128,576 total
includes taxes & fees
Oct 26 - Oct 27
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
A modern kitchen with a central island, a dining area with a table and chairs, and a hallway leading to another room.

19. Perfect 4-bedroom house with AC in tranquil Albany

Perfect 4-bedroom house with AC in tranquil Albany
Delaware Avenue
10.0 out of 10, Exceptional, (3 reviews)
"The place so clean and beautiful we enjoyed the game refreshed my boy time memories and space and rooms so unique. I will definitely recommend that place then hotel. It’s more than five stars hotel."
United States
Alex
The price is ￥42,636
￥85,613 total
includes taxes & fees
Oct 7 - Oct 8
Perfect 4-bedroom house with AC in tranquil Albany
A staircase with a wooden handrail and a white wall with a light switch.

20. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (28 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 ￥32,107
￥50,145 total
includes taxes & fees
Oct 7 - Oct 8
Leaf-Peeper Paradise in the Berkshires
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

10/10 Excellent
"Love the fireplace in our room! The amenities always make this place worth the money, and the views to top it all off!!"
Jennifer 1-night trip
Posted 7 hours ago
Vacation Village in the Berkshires

Find out more about Old Chatham

Old Chatham Vacation Homes information

Number of reviews
159
Accommodation
434 Vacation Homes
Lowest Price
￥21,600
Highest Price
￥128,576