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Our top choices for Old Chatham vacation 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 ¥17,023
¥22,657 total
includes taxes & fees
Jun 7 - Jun 8
All the comforts of home

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 ¥8,656
¥21,466 total
includes taxes & fees
Jun 9 - Jun 10
Albany Retreat- Free Breakfast & Parking Included

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (15 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ¥37,075
¥56,275 total
includes taxes & fees
Jun 18 - Jun 19
Cozy Riverside Berkshires Retreat

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
The price is ¥23,082
¥58,011 total
includes taxes & fees
Jun 8 - Jun 9
stylish Berkshires Retreat

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 ¥34,046
¥74,936 total
includes taxes & fees
Jun 9 - Jun 10
Near Tanglewood: Historic Summer Retreat

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 ¥34,190
¥55,347 total
includes taxes & fees
Jun 9 - Jun 10
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

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 ¥32,002
¥54,480 total
includes taxes & fees
Jun 14 - Jun 15
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

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 ¥46,608
¥79,312 total
includes taxes & fees
Jun 9 - Jun 10
Treat yourself at the stunning June Farms Wellness Huts!

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 ¥28,051
¥90,300 total
includes taxes & fees
Jun 7 - Jun 8
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

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 ¥39,271
¥89,942 total
includes taxes & fees
Jun 8 - Jun 9
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

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 ¥27,730
¥65,783 total
includes taxes & fees
Jun 8 - Jun 9
Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking

“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 ¥28,708
¥69,954 total
includes taxes & fees
Jun 14 - Jun 15
“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, (32 reviews)
"Everything was as advertised!"
United States
Jessica S.
The price is ¥38,229
¥58,458 total
includes taxes & fees
Jun 14 - Jun 15
Home in Great Barrington

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 ¥36,065
¥83,120 total
includes taxes & fees
Jun 7 - Jun 8
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

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 ¥25,678
¥64,306 total
includes taxes & fees
Jun 9 - Jun 10
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 ¥28,171
¥86,666 total
includes taxes & fees
Jun 22 - Jun 23
Charles Cottage Near Warren St New Renovation

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 ¥26,256
¥65,490 total
includes taxes & fees
Jun 10 - Jun 11
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

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, (2 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 ¥44,721
¥88,634 total
includes taxes & fees
Jun 17 - Jun 18
Perfect 4-bedroom house with AC in tranquil Albany

Larkspire I Sleepy Hollow Lake I Beach & Firepit

Larkspire I Sleepy Hollow Lake I Beach & Firepit
Athens
The price is ¥37,764
¥81,812 total
includes taxes & fees
Jun 8 - Jun 9
Larkspire I Sleepy Hollow Lake I Beach & Firepit

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
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is ¥50,347
¥88,466 total
includes taxes & fees
Jun 9 - Jun 10
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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

Find out more about Old Chatham

Old Chatham Vacation Homes information

Number of reviews
153
Accommodation
465 Vacation Homes
Lowest Price
¥21,466
Highest Price
¥90,300