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Our top choices for Old Chatham holiday homes

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (32 reviews)
"The location was just what we were looking for, the cabin was cozy and clean, and the host was so helpful and welcoming!"
United States
Olivia C.
The price is £108
includes taxes & fees
4 Jun - 5 Jun
All the comforts of home

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is £232
includes taxes & fees
8 Jun - 9 Jun
Cozy Riverside Berkshires Retreat

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
The price is £293
includes taxes & fees
8 Jun - 9 Jun
stylish Berkshires Retreat

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 £102
includes taxes & fees
8 Jun - 9 Jun
Albany Retreat- Free Breakfast & Parking Included

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is £287
includes taxes & fees
7 Jun - 8 Jun
Near Tanglewood: Historic Summer Retreat

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, (2 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 £381
includes taxes & fees
4 Jun - 5 Jun
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

“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
10.0 out of 10, Exceptional, (1 review)
"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 £333
includes taxes & fees
14 Jun - 15 Jun
“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (31 reviews)
"Everything was as advertised!"
United States
Jessica S.
The price is £259
includes taxes & fees
14 Jun - 15 Jun
Home in Great Barrington

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.6 out of 10, Exceptional, (5 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is £251
includes taxes & fees
4 Jun - 5 Jun
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Hudson’
The price is £224
includes taxes & fees
9 Jun - 10 Jun
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is £409
includes taxes & fees
4 Jun - 5 Jun
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

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 £368
includes taxes & fees
4 Jun - 5 Jun
Treat yourself at the stunning June Farms Wellness Huts!

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
9.0 out of 10, Wonderful, (2 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 £303
includes taxes & fees
8 Jun - 9 Jun
Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking

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, (6 reviews)
"Our host was fantastic! She allowed us to check in early and check out late. The house was cozy and perfect for my girls weekend! "
United States
Kim W.
The price is £388
includes taxes & fees
4 Jun - 5 Jun
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

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 £518
includes taxes & fees
8 Jun - 9 Jun
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is £389
includes taxes & fees
4 Jun - 5 Jun
Cozy. Clean. Free bagel shop. 3 Fireplaces.

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
The price is £297
includes taxes & fees
4 Jun - 5 Jun
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is £295
includes taxes & fees
8 Jun - 9 Jun
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is £405
includes taxes & fees
22 Jun - 23 Jun
Charles Cottage Near Warren St New Renovation

Perfect 4-bedroom house with AC in tranquil Albany

Perfect 4-bedroom house with AC in tranquil Albany
Whitehall
10.0 out of 10, Exceptional, (1 review)
"Great stay! Only recommendation is fans or AC"
United States
William D.
The price is £421
includes taxes & fees
10 Jun - 11 Jun
Perfect 4-bedroom house with AC in tranquil Albany
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

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Old Chatham Holiday Homes information

Number of reviews
151
Accommodation
465 Holiday Homes
Lowest Price
£102
Highest Price
£518