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

Holiday Homes in Old Chatham

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Old Chatham holiday homes

A modern building with a wooden deck and a door.

1. 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 AU$975
includes taxes & fees
29 Sept - 30 Sept
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
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
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is AU$301
includes taxes & fees
29 Sept - 30 Sept
NEW RENO - Chalet-style farm loft near Tanglewood
A camping setup with a metal chair and a table by a river in a forest.

3. 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 AU$483
includes taxes & fees
29 Sept - 30 Sept
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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 AU$326
includes taxes & fees
29 Sept - 30 Sept
1800s Carriage house in Berkshires / Hudson Valley
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 AU$675
includes taxes & fees
30 Sept - 1 Oct
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

6. 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 AU$810
includes taxes & fees
5 Oct - 6 Oct
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
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, (37 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is AU$204
includes taxes & fees
1 Oct - 2 Oct
All the comforts of home
A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery and trees.

8. 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 AU$544
includes taxes & fees
30 Sept - 1 Oct
Treat yourself at the stunning June Farms Wellness Huts!
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, (7 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is AU$774
includes taxes & fees
29 Sept - 30 Sept
NEW RENO Historic Creamery in Berkshires w/hot tub
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.

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

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is AU$969
includes taxes & fees
5 Oct - 6 Oct
Ellie’s Overlook, best view in the Berkshires!
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

11. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (27 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 AU$449
includes taxes & fees
29 Sept - 30 Sept
Riverside Retreat in the Berkshires
A wooden deck with benches and a pergola, surrounded by a garden with potted plants and a barbecue grill.

12. Tranquil 2-bedroom townhome with AC in charming Troy

Tranquil 2-bedroom townhome with AC in charming Troy
Troy
Tranquil 2-bedroom townhome with AC in charming Troy
A modern kitchen with a central island, a dining area with a table and chairs, and a hallway leading to another room.

13. 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 AU$783
includes taxes & fees
29 Sept - 30 Sept
Perfect 4-bedroom house with AC in tranquil Albany
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 AU$1,499
includes taxes & fees
11 Oct - 12 Oct
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
A covered patio with a dining table, chairs, a sofa, and a stone wall.

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

Lakefront Retreat Hot Tub, Dock, Kayaks, & Firepit
Averill Park
The price is AU$1,028
includes taxes & fees
29 Sept - 30 Sept
Lakefront Retreat Hot Tub, Dock, Kayaks, & Firepit
A balcony with a white wooden table, a glass vase with white flowers, and a view of a residential street and trees during sunset.

16. “The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany

“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany
Pine Hills
9.6 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay at this property and will rent again when in the area. The owners were very responsive and great to work with. The apt was beautiful and immaculate. We enjoyed our stay very much. The only area that was perfect was the outside stairs to the front door— uneven, steep, etc. We had older guest with us and this was concerning. But we managed. Thanks again for a great stay"
United States
Melissa A.
The price is AU$615
includes taxes & fees
4 Oct - 5 Oct
“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany
A wooden deck with a wicker sofa, a hammock, and a grill.

17. Larkspire I Sleepy Hollow Lake I Beach & Firepit

Larkspire I Sleepy Hollow Lake I Beach & 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$800
includes taxes & fees
29 Sept - 30 Sept
Larkspire I Sleepy Hollow Lake I Beach & Firepit
A hotel lobby with a leather sofa, a coffee table, and a dining area with tables and chairs.

18. 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$196
includes taxes & fees
6 Oct - 7 Oct
Albany Retreat- Free Breakfast & Parking Included
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 AU$1,139
includes taxes & fees
13 Oct - 14 Oct
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

20. 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)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is AU$488
includes taxes & fees
13 Oct - 14 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"The problem with the suites is that the cooking smell of the adjoining kitchen can really permeate throughout the entire space. So whoever cooked like a tomato sauce or something before I was there, I could really smell it in the bedroom. The bed was very comfortable though. The room was clean. The bathroom could use some updating. The staff were very nice."
Bridget 1-night trip
Posted less than an hour ago
Berkshire Mountain Lodge

Find out more about Old Chatham

Old Chatham Holiday Homes information

Number of reviews
147
Accommodation
436 Holiday Homes
Lowest Price
AU$196
Highest Price
AU$1,499