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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 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
8.6 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 AED 257
AED 764 total
includes taxes & fees
20 Oct - 21 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A camping setup with a metal chair and a table by a river in a forest.

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, (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 1,263 total
includes taxes & fees
19 Oct - 20 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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 929
AED 2,234 total
includes taxes & fees
19 Oct - 20 Oct
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A spacious living room with a dining area, a kitchen, and a large window.

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 827 total
includes taxes & fees
9 Nov - 10 Nov
1800s Carriage house in Berkshires / Hudson Valley
A cozy living room with a sofa, a fireplace, and large windows.

5. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is AED 1,405
AED 2,495 total
includes taxes & fees
21 Oct - 22 Oct
Luxury Barn Near Hudson With New Private Sauna
A white two-story house with a porch, surrounded by trees and a hill.

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 738
AED 1,740 total
includes taxes & fees
19 Oct - 20 Oct
1789 Shaker Farmhouse in Berkshires/Hudson Valley
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, (8 reviews)
"A lovely house! Very convenient for a Tanglewood weekend."
United States
Robert B.
The price is AED 646
AED 2,075 total
includes taxes & fees
19 Oct - 20 Oct
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 519 total
includes taxes & fees
19 Oct - 20 Oct
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 1,021
AED 2,109 total
includes taxes & fees
27 Oct - 28 Oct
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 AED 198
AED 492 total
includes taxes & fees
19 Oct - 20 Oct
Albany Retreat- Free Breakfast & Parking Included
A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery and trees.

11. 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 952
AED 1,689 total
includes taxes & fees
28 Oct - 29 Oct
Treat yourself at the stunning June Farms Wellness Huts!
A couple in a hot tub with a natural landscape in the background.

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, (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 2,147 total
includes taxes & fees
26 Oct - 27 Oct
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
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.

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

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is AED 1,157
AED 2,538 total
includes taxes & fees
25 Oct - 26 Oct
Ellie’s Overlook, best view in the Berkshires!
A bedroom with a bed, a nightstand, a lamp, a chair, and a dresser.

14. Mayas Shangrila

Mayas Shangrila
2.0 star property
Richmond
The price is AED 2,983
AED 4,260 total
includes taxes & fees
19 Oct - 20 Oct
Mayas Shangrila
A cozy living room with a wooden bookshelf, a sofa set, a dining table with chairs, and a patterned rug.

15. Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires

Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires
Richmond
The price is AED 3,306
AED 4,614 total
includes taxes & fees
20 Oct - 21 Oct
Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires
A modern kitchen with white cabinets, a wooden countertop, and a large TV mounted on the wall.

16. 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 602
AED 1,452 total
includes taxes & fees
17 Nov - 18 Nov
Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking
A staircase with a wooden handrail and a white wall with a light switch.

17. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 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 AED 645
AED 1,036 total
includes taxes & fees
28 Oct - 29 Oct
Leaf-Peeper Paradise in the Berkshires
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

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 AED 1,253
AED 2,372 total
includes taxes & fees
20 Oct - 21 Oct
Secluded Family Home in Serene Stockbridge Woods
A wooden deck with a wicker sofa, a hammock, and a grill.

19. Larkspire l Catskills Fall Foliage Lake House

Larkspire l Catskills Fall Foliage Lake House
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 AED 1,008
AED 2,045 total
includes taxes & fees
20 Oct - 21 Oct
Larkspire l Catskills Fall Foliage Lake House
Pool

20. 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 AED 657
AED 2,063 total
includes taxes & fees
14 Nov - 15 Nov
Comfortable Berkshires retreat on mtn resort, SISO
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"-"
Serena 1-night trip
Posted 1 hour ago
Quality Inn Great Barrington