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Our top choices for Chatham vacation homes

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (6 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is AED 845
AED 1,395 total
includes taxes & fees
21 Jun - 22 Jun
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is AED 735
AED 1,234 total
includes taxes & fees
21 Jun - 22 Jun
Sugar Shack - 300 square feet of pure sweetness.

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, (3 reviews)
The price is AED 885
AED 2,040 total
includes taxes & fees
23 Jun - 24 Jun
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.6 out of 10, Exceptional, (4 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is AED 643
AED 2,037 total
includes taxes & fees
21 Jun - 22 Jun
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (32 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is AED 390
AED 519 total
includes taxes & fees
30 Jun - 1 Jul
All the comforts of home

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
10.0 out of 10, Exceptional, (1 review)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is AED 780
AED 1,745 total
includes taxes & fees
22 Jun - 23 Jun
stylish Berkshires Retreat

Catskill Stay w/ Deck & Fire Pit

Catskill Stay w/ Deck & Fire Pit
Catskill
9.0 out of 10, Wonderful, (4 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 AED 506
AED 1,560 total
includes taxes & fees
24 Jun - 25 Jun
Catskill Stay w/ Deck & Fire Pit

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (16 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 1,155 total
includes taxes & fees
22 Jun - 23 Jun
Cozy Riverside Berkshires Retreat

Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (11 reviews)
"We had an excellent experience. The place was wonderful. A real place to disconnect from everything. We Highly recommend it."
United States
Saul
The price is AED 588
AED 1,269 total
includes taxes & fees
6 Jul - 7 Jul
Modern Luxurious Cabin, Catskills - The Tiny Nook

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (32 reviews)
"Perfect space for an overnight stay. Very clean and well appointed. Communication from host was great and check in was a breeze. 2 minute drive from downtown Great Barrington."
United States
Anonymous traveler
The price is AED 876
AED 1,348 total
includes taxes & fees
22 Jun - 23 Jun
Home in Great Barrington

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 AED 840
AED 1,327 total
includes taxes & fees
22 Jun - 23 Jun
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is AED 549
AED 1,853 total
includes taxes & fees
23 Jun - 24 Jun
Charles Cottage Near Warren St New Renovation

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 AED 545
AED 1,413 total
includes taxes & fees
24 Jun - 25 Jun
Near Tanglewood: Historic Summer Retreat

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 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 1,172
AED 2,302 total
includes taxes & fees
22 Jun - 23 Jun
Treetop Hideaway in Tyringham

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 1,154
AED 2,019 total
includes taxes & fees
21 Jun - 22 Jun
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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 1,068
AED 1,817 total
includes taxes & fees
16 Jul - 17 Jul
Treat yourself at the stunning June Farms Wellness Huts!

Larkspire I Sleepy Hollow Lake I Beach & Firepit

Larkspire I Sleepy Hollow Lake I Beach & Firepit
Athens
Larkspire I Sleepy Hollow Lake I Beach & Firepit

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, (7 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 AED 1,634
AED 2,925 total
includes taxes & fees
26 Jun - 27 Jun
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is AED 1,570
AED 2,915 total
includes taxes & fees
25 Jun - 26 Jun
Spacious 5-bedroom house in charming Lee with WiFi

NEW: Chic Family Home in Boutique Town

NEW: Chic Family Home in Boutique Town
Catskill
10.0 out of 10, Exceptional, (1 review)
"As described."
United States
kimberly j.
The price is AED 695
AED 2,597 total
includes taxes & fees
22 Jun - 23 Jun
NEW: Chic Family Home in Boutique Town
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