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Holiday Homes in Chatham

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Check prices for these dates

In two weeks
17 July - 19 July
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Chatham holiday homes

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, (9 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is AU$544
includes taxes & fees
8 July - 9 July
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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 AU$871
includes taxes & fees
7 July - 8 July
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Property grounds

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 AU$208
includes taxes & fees
5 July - 6 July
All the comforts of home
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 AU$490
includes taxes & fees
8 July - 9 July
Modern Luxurious Cabin, Catskills - The Tiny Nook
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (18 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AU$470
includes taxes & fees
1 July - 2 July
Cozy Riverside 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 AU$683
includes taxes & fees
6 July - 7 July
Catskill Stay w/ Deck & Fire Pit
Exterior

Modern cabin retreat

Modern cabin retreat
Catskill
The price is AU$403
includes taxes & fees
6 July - 7 July
Modern cabin retreat
Exterior

Cozy Catskill Escape

Cozy Catskill Escape
Catskill
The price is AU$395
includes taxes & fees
6 July - 7 July
Cozy Catskill Escape
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 AU$815
includes taxes & fees
1 July - 2 July
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
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 AU$631
includes taxes & fees
13 July - 14 July
stylish Berkshires Retreat
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 AU$875
includes taxes & fees
1 July - 2 July
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
TV

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is AU$740
includes taxes & fees
5 July - 6 July
Charles Cottage Near Warren St New Renovation
Outdoor spa tub

Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is AU$410
includes taxes & fees
8 July - 9 July
Cabin Oasis near Town
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is AU$994
includes taxes & fees
6 July - 7 July
Treetop Hideaway in Tyringham
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 AU$522
includes taxes & fees
1 July - 2 July
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 AU$812
includes taxes & fees
9 July - 10 July
Treat yourself at the stunning June Farms Wellness Huts!
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.
Sweet Cozy Victorian in Housatonic. Close to everything.
TV, fireplace, ping pong, books

NEW: Gorgeous Grand Chalet w/ Hot Tub & Views

NEW: Gorgeous Grand Chalet w/ Hot Tub & Views
Catskill
The price is AU$1,245
includes taxes & fees
1 July - 2 July
NEW: Gorgeous Grand Chalet w/ Hot Tub & Views
Outdoor dining

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.
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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 AU$1,296
includes taxes & fees
1 July - 2 July
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

Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

10/10 Excellent
"I didn't have enough time to thoroughly check out the amenities, but what I did see was great!"
Joe 1-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Downtown Albany New York

Find out more about Chatham

Chatham Holiday Homes information

Number of reviews
9,365
Accommodation
499 Holiday Homes
Lowest Price
AU$93
Highest Price
AU$375