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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

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)
"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 €184
includes taxes & fees
10 Sept - 11 Sept
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.
The price is €641
includes taxes & fees
7 Sept - 8 Sept
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.

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, (13 reviews)
"This property is really nice. House is beautiful and the man cave is a nice addition. Wish we were there long enough to use it."
United States
Jen R.
The price is €297
includes taxes & fees
20 Sept - 21 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 €201
includes taxes & fees
14 Sept - 15 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 €428
includes taxes & fees
9 Sept - 10 Sept
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 €497
includes taxes & fees
16 Sept - 17 Sept
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, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is €126
includes taxes & fees
7 Sept - 8 Sept
All the comforts of home
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

8. 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 €449
includes taxes & fees
14 Sept - 15 Sept
NEW RENO Historic Creamery in Berkshires w/hot tub
A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery and trees.

9. 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 €426
includes taxes & fees
14 Sept - 15 Sept
Treat yourself at the stunning June Farms Wellness Huts!
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

10. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is €277
includes taxes & fees
8 Sept - 9 Sept
Cozy Riverside Berkshires Retreat
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

11. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 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 €276
includes taxes & fees
9 Sept - 10 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
A modern kitchen with white cabinets, a wooden countertop, and a large TV mounted on the wall.

12. 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, (7 reviews)
"This property is just as listed. Very clean, comfortable, pet, friendly, and comes with all necessities. From booking to check out, everything went extremely smooth!"
United States
Lisette T.
The price is €318
includes taxes & fees
8 Sept - 9 Sept
Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking
A hotel lobby with a leather sofa, a coffee table, and a dining area with tables and chairs.

13. 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 €119
includes taxes & fees
7 Sept - 8 Sept
Albany Retreat- Free Breakfast & Parking Included
A modern kitchen with a central island, built-in appliances, and a dining area with a round table.

14. 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 €653
includes taxes & fees
7 Sept - 8 Sept
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
A balcony with a white wooden table, a glass vase with white flowers, and a view of a residential street and trees during sunset.

15. “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 €379
includes taxes & fees
13 Sept - 14 Sept
“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.

16. Larkspire I Sleepy Hollow Lake I Beach & Firepit

Larkspire I Sleepy Hollow Lake I Beach & Firepit
Athens
The price is €451
includes taxes & fees
30 Sept - 1 Oct
Larkspire I Sleepy Hollow Lake I Beach & Firepit
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.

17. Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
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 €425
includes taxes & fees
30 Sept - 1 Oct
Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

18. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is €314
includes taxes & fees
8 Sept - 9 Sept
Home in Great Barrington
A wooden deck with a table and chairs, surrounded by a white railing.

19. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very good, (10 reviews)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is €466
includes taxes & fees
8 Sept - 9 Sept
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

20. 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 €922
includes taxes & fees
9 Sept - 10 Sept
Hancock Village Inn Near Jiminy Peak
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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"Clean, great location and affordable."
Bryan 1-night trip
Posted 1 hour ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Old Chatham

Old Chatham Holiday Homes information

Number of reviews
168
Accommodation
436 Holiday Homes
Lowest Price
€119
Highest Price
€922