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Our top choices for Chatham vacation homes

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
2.0 star property
Chatham
The price is ¥27,753
¥48,313 total
includes taxes & fees
Jan 25 - Jan 26
Renovated house. Built in 1890s. No neighbors in sight.

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is ¥21,410
¥58,970 total
includes taxes & fees
Jan 19 - Jan 20
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is ¥23,122
¥39,645 total
includes taxes & fees
Jan 26 - Jan 27
Home in Great Barrington

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.4 out of 10, Exceptional, (3 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is ¥28,462
¥72,767 total
includes taxes & fees
Jan 19 - Jan 20
Sun Filled Lenox Retreat - Minutes to Tanglewood!

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (29 reviews)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
The price is ¥18,658
¥24,439 total
includes taxes & fees
Feb 2 - Feb 3
All the comforts of home

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.2 out of 10, Wonderful, (25 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is ¥18,983
¥55,898 total
includes taxes & fees
Jan 20 - Jan 21
Near Tanglewood: Historic Summer Retreat

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
2.0 star property
Stephentown
8.0 out of 10, Very Good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is ¥27,671
¥89,077 total
includes taxes & fees
Jan 29 - Jan 30
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
10.0 out of 10, Exceptional, (3 reviews)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is ¥21,346
¥42,389 total
includes taxes & fees
Feb 9 - Feb 10
Sweet Cozy Victorian in Housatonic. Close to everything.

Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking

Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking
2.0 star property
Albany
8.0 out of 10, Very Good, (1 review)
"Overall nice stay "
United States
Anonymous traveler
The price is ¥29,252
¥45,766 total
includes taxes & fees
Jan 29 - Jan 30
Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking

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 ¥39,277
¥70,801 total
includes taxes & fees
Jan 27 - Jan 28
Treat yourself at the stunning June Farms Wellness Huts!

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.2 out of 10, Wonderful, (7 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ¥32,019
¥47,069 total
includes taxes & fees
Jan 26 - Jan 27
Family Ski Getaway in the Berkshires

Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (8 reviews)
"Great place. Exactly like the pictures. "
United States
robert a.
The price is ¥25,299
¥54,475 total
includes taxes & fees
Jan 27 - Jan 28
Modern Luxurious Cabin, Catskills - The Tiny Nook

Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape
2.0 star property
Stottville
The price is ¥26,286
¥53,570 total
includes taxes & fees
Jan 19 - Jan 20
Hudson Hot Tub & Pet Escape

Suite 3 - Quiet and private accommodations in a country setting.

Suite 3 - Quiet and private accommodations in a country setting.
Spencertown
10.0 out of 10, Exceptional, (1 review)
"Fantastic place to stay!"
United States
James
The price is ¥33,680
¥43,034 total
includes taxes & fees
Jan 27 - Jan 28
Suite 3 - Quiet and private accommodations in a country setting.

Catskill Stay w/ Deck & Fire Pit

Catskill Stay w/ Deck & Fire Pit
Catskill
8.8 out of 10, Excellent, (3 reviews)
"we had a great stay at this house with a group of friends - rooms were comfortable and kitchen had a lot of things we needed for meals. "
United States
raquel p.
The price is ¥24,207
¥70,344 total
includes taxes & fees
Jan 21 - Jan 22
Catskill Stay w/ Deck & Fire Pit

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is ¥34,731
¥54,915 total
includes taxes & fees
Feb 17 - Feb 18
3-bedroom house in beautiful Berkshires, close to amenities!

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Monterey
10.0 out of 10, Exceptional, (1 review)
"Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."
United States
Kim H.
The price is ¥134,086
¥273,630 total
includes taxes & fees
Jan 18 - Jan 19
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (32 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is ¥47,278
¥102,792 total
includes taxes & fees
Feb 10 - Feb 11
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

1 Bedroom | Cozy Lounge | Spacious

1 Bedroom | Cozy Lounge | Spacious
2.0 star property
Catskill
1 Bedroom | Cozy Lounge | Spacious
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 Chatham Hotel Reviews

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Chatham Vacation Homes information

Number of reviews
150
Accommodation
490 Vacation Homes
Lowest Price
¥24,439
Highest Price
¥273,630