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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Chatham holiday homes

Exterior detail

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)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is £437
includes taxes & fees
28 Jun - 29 Jun
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Property grounds

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, (8 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is £291
includes taxes & fees
29 Jun - 30 Jun
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Exterior

Cozy Catskill Escape

Cozy Catskill Escape
Catskill
The price is £206
includes taxes & fees
28 Jun - 29 Jun
Cozy Catskill Escape
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (32 reviews)
The price is £110
includes taxes & fees
1 Jul - 2 Jul
All the comforts of home
Exterior

Modern cabin retreat

Modern cabin retreat
Catskill
The price is £212
includes taxes & fees
30 Jun - 1 Jul
Modern cabin retreat
Outdoor spa tub

Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is £212
includes taxes & fees
30 Jun - 1 Jul
Cabin Oasis near Town
Exterior

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 £261
includes taxes & fees
29 Jun - 30 Jun
Modern Luxurious Cabin, Catskills - The Tiny Nook
Interior

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 £250
includes taxes & fees
8 Jul - 9 Jul
Cozy Riverside Berkshires Retreat
Smart TV

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 £334
includes taxes & fees
1 Jul - 2 Jul
stylish Berkshires Retreat
TV, offices

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 £342
includes taxes & fees
29 Jun - 30 Jun
Catskill Stay w/ Deck & Fire Pit
TV

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is £380
includes taxes & fees
30 Jun - 1 Jul
Charles Cottage Near Warren St New Renovation
Fridge, microwave, stovetop, dishwasher

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 £418
includes taxes & fees
28 Jun - 29 Jun
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Pool

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 £411
includes taxes & fees
30 Jun - 1 Jul
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Fridge, microwave, oven, stovetop

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 £588
includes taxes & fees
30 Jun - 1 Jul
NEW: Chic Family Home in Boutique Town
Outdoor dining

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 £267
includes taxes & fees
30 Jun - 1 Jul
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Terrace/patio

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)
"Loved the wellness hut. Our sauna didnt work however the room was spacious and comfy. The staff is very attentive and we also enjoyed the soup stroll. Would def recommend."
United States
Lauren C.
The price is £425
includes taxes & fees
9 Jul - 10 Jul
Treat yourself at the stunning June Farms Wellness Huts!
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (33 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 traveller
The price is £327
includes taxes & fees
19 Jul - 20 Jul
Home in Great Barrington
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is £378
includes taxes & fees
28 Jun - 29 Jun
Cheerful 3-bedroom cottage with woodstove
TV

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 £495
includes taxes & fees
29 Jun - 30 Jun
Treetop Hideaway in Tyringham
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (7 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is £352
includes taxes & fees
29 Jun - 30 Jun
Sweet Cozy Victorian in Housatonic. Close to everything.
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

Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

10/10 Excellent
"Spacious and clean rooms."
Ramchand 1-night trip
Posted 9 hours ago
Country Inn & Suites by Radisson, Downtown Albany New York

Find out more about Chatham

Chatham Holiday Homes information

Number of reviews
189
Accommodation
521 Holiday Homes
Lowest Price
£110
Highest Price
£588