A brick building with a green dome and columns, labeled "TRACY MEMORIAL VILLAGE HALL".

Search Vacation Homes in Old Chatham

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Old Chatham holiday 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 HK$549
HK$1,631 total
includes taxes & fees
27 Oct - 28 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

2. 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$667
HK$1,766 total
includes taxes & fees
5 Nov - 6 Nov
1800s Carriage house in Berkshires / Hudson Valley
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 HK$2,580
HK$5,525 total
includes taxes & fees
27 Oct - 28 Oct
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Exterior

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, (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 HK$1,567
HK$2,686 total
includes taxes & fees
25 Oct - 26 Oct
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 HK$1,419
HK$3,506 total
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 HK$3,000
HK$5,327 total
includes taxes & fees
27 Oct - 28 Oct
Luxury Barn Near Hudson With New Private Sauna
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
9.2 out of 10, Wonderful, (10 reviews)
"A lovely house! Very convenient for a Tanglewood weekend."
United States
Robert B.
The price is HK$1,592
HK$4,666 total
includes taxes & fees
25 Oct - 26 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 HK$832
HK$1,108 total
includes taxes & fees
2 Nov - 3 Nov
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 traveller
The price is HK$2,179
HK$4,500 total
includes taxes & fees
27 Oct - 28 Oct
NEW RENO Historic Creamery in Berkshires w/hot tub
A lobby with a brown leather sofa set, a patterned carpet, and a chandelier.

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$423
HK$1,050 total
includes taxes & fees
27 Oct - 28 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 HK$2,031
HK$3,603 total
includes taxes & fees
3 Nov - 4 Nov
Treat yourself at the stunning June Farms Wellness Huts!
A spacious room with wooden flooring, a black and white bench, a small table with a plant, and a door leading to an outdoor area.

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 HK$2,039
HK$4,585 total
includes taxes & fees
27 Oct - 28 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 HK$2,469
HK$5,416 total
includes taxes & fees
11 Nov - 12 Nov
Ellie’s Overlook, best view in the Berkshires!
A modern kitchen with white cabinets, a wooden countertop, and a large TV mounted on the wall.

14. 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 HK$1,106
HK$2,897 total
includes taxes & fees
26 Oct - 27 Oct
Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking
A dining area with a wooden table and chairs, a ceiling fan, and a view of the outdoors through windows.

15. 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 HK$1,376
HK$2,212 total
includes taxes & fees
26 Oct - 27 Oct
Leaf-Peeper Paradise in the Berkshires
Pool

16. 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$4,243 total
includes taxes & fees
25 Oct - 26 Oct
Comfortable Berkshires retreat on mtn resort, SISO
A wooden deck with a wicker sofa, a hammock, and a grill.

17. 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 HK$2,153
HK$4,375 total
includes taxes & fees
26 Oct - 27 Oct
Larkspire l Catskills Fall Foliage Lake House
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 HK$2,970
HK$5,445 total
includes taxes & fees
2 Nov - 3 Nov
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.

19. 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$3,451
HK$6,386 total
includes taxes & fees
18 Nov - 19 Nov
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
A living room with a fireplace, a television mounted above it, and a sofa.

20. 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$2,670
HK$4,065 total
includes taxes & fees
31 Oct - 1 Nov
Downtown 3BR duplex full kitchen parking off i-787
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Old Chatham Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"beautiful location, giant suite room for incredible value"
Michael 4-night trip
Posted less than an hour ago
Berkshire Mountain Lodge

Find out more about Old Chatham

Old Chatham Vacation Homes information

Number of reviews
187
Accommodation
434 Vacation Homes
Lowest Price
HK$1,050
Highest Price
HK$6,386

Explore a world of travel with Expedia