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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.
Chatham
8.0 out of 10, Very Good, (1 review)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is AED 643
AED 1,135 total
includes taxes & fees
1 Apr - 2 Apr
Renovated house. Built in 1890s. No neighbors in sight.

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (31 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 AED 433
AED 568 total
includes taxes & fees
23 Apr - 24 Apr
All the comforts of home

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is AED 754
AED 1,170 total
includes taxes & fees
13 Apr - 14 Apr
Home in Great Barrington

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is AED 450
AED 1,298 total
includes taxes & fees
5 Apr - 6 Apr
Near Tanglewood: Historic Summer Retreat

Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (20 reviews)
"Great little place to stay at right in downtown!!"
United States
Bryan S.
Catskill Cottage Walk to Downtown & River Views

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AED 744
AED 1,163 total
includes taxes & fees
1 Apr - 2 Apr
Cozy Riverside Berkshires Retreat

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 AED 912
AED 1,645 total
includes taxes & fees
1 Apr - 2 Apr
Treat yourself at the stunning June Farms Wellness Huts!

Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (10 reviews)
"Great place. Exactly like the pictures. "
United States
robert a.
The price is AED 588
AED 1,230 total
includes taxes & fees
8 Apr - 9 Apr
Modern Luxurious Cabin, Catskills - The Tiny Nook

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 AED 823
AED 1,782 total
includes taxes & fees
1 Apr - 2 Apr
Historic Berkshires Home Near Tanglewood, Trails & Wineries

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 AED 988
AED 1,810 total
includes taxes & fees
1 Apr - 2 Apr
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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.
Catskill Stay w/ Deck & Fire Pit

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is AED 593
AED 1,885 total
includes taxes & fees
2 Apr - 3 Apr
Artists’ Hideaway in Old Chatham

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 871
AED 1,855 total
includes taxes & fees
1 Apr - 2 Apr
Cheerful 3-bedroom cottage with woodstove

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, (35 reviews)
"A very special, well equipped, and comfortable house with a great kitchen, bedrooms and bathrooms as well as a lovely enclosed porch and outdoor area in an amazing location. Wonderful home with all amenities and thoughtful details provided for guests. A short walk to charming town and across from a beautiful hiking area. Excellent stay!"
United States
Susan
The price is AED 1,319
AED 2,659 total
includes taxes & fees
1 Apr - 2 Apr
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

NEW: Chic Colonial - Family, Fun, Food & Forays!

NEW: Chic Colonial - Family, Fun, Food & Forays!
Catskill
The price is AED 717
AED 2,667 total
includes taxes & fees
8 Apr - 9 Apr
NEW: Chic Colonial - Family, Fun, Food & Forays!

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is AED 970
AED 2,042 total
includes taxes & fees
1 Apr - 2 Apr
Treetop Hideaway in Tyringham

Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape
Stottville
10.0 out of 10, Exceptional, (2 reviews)
The price is AED 624
AED 1,152 total
includes taxes & fees
7 Apr - 8 Apr
Hudson Hot Tub & Pet Escape

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is AED 2,079
AED 4,879 total
includes taxes & fees
6 Apr - 7 Apr
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (2 reviews)
"Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! "
United States
Timothy S.
Luxury Barn Retreat — All-Season Escape Awaits!

Tao Estate in Catskills : Close to Hiking & Nature & Pet Friendly

Tao Estate in Catskills : Close to Hiking & Nature & Pet Friendly
CATSKILL
9.4 out of 10, Exceptional, (3 reviews)
"Lovely short weekend in the countryside. Calm zen retreat surrounded by nature and animals."
United States
sarah j.
The price is AED 1,322
AED 2,717 total
includes taxes & fees
7 Apr - 8 Apr
Tao Estate in Catskills : Close to Hiking & Nature & Pet Friendly
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