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Our top choices for Chatham holiday homes

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (18 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is £242
includes taxes & fees
12 Nov - 13 Nov
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

2. 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, (5 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 £428
includes taxes & fees
16 Nov - 17 Nov
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

3. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is £100
includes taxes & fees
18 Nov - 19 Nov
All the comforts of home

4. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is £162
includes taxes & fees
12 Nov - 13 Nov
1800s Carriage house in Berkshires / Hudson Valley

5. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.8 out of 10, Excellent, (8 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is £148
includes taxes & fees
19 Nov - 20 Nov
NEW RENO - Chalet-style farm loft near Tanglewood

6. Blue Heron House - Creekside 3BR - Hot Tub, Sauna & Fire Pit - 10min to Hudson

Blue Heron House - Creekside 3BR - Hot Tub, Sauna & Fire Pit - 10min to Hudson
Hudson
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful house and wonderful host. I very much hope we get to stay again in the future. "
United States
Jeffrey D.
The price is £275
includes taxes & fees
12 Nov - 13 Nov
Blue Heron House - Creekside 3BR - Hot Tub, Sauna & Fire Pit - 10min to Hudson

7. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is £304
includes taxes & fees
18 Nov - 19 Nov
1789 Shaker Farmhouse in Berkshires/Hudson Valley

8. 2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Stottville
The price is £537
includes taxes & fees
17 Nov - 18 Nov
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

9. Modern Family Home · Walk to Lake · Firepit

Modern Family Home · Walk to Lake · Firepit
Athens
10.0 out of 10, Exceptional, (2 reviews)
"Lovely home with reasonable accessibility. Host was very responsive. Clean and quiet. Beautiful scenery."
United States
Kellie H.
The price is £408
includes taxes & fees
15 Nov - 16 Nov
Modern Family Home · Walk to Lake · Firepit

10. Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren

Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
Hudson
10.0 out of 10, Exceptional, (7 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
United States
Brittaney O.
The price is £322
includes taxes & fees
18 Nov - 19 Nov
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren

11. Charming Hudson Valley Escape | Autumn Vibes & Fire Pit

Charming Hudson Valley Escape | Autumn Vibes & Fire Pit
Claverack-Red Mills
10.0 out of 10, Exceptional, (1 review)
"amazing property - best rental i’ve ever stayed at. can’t recommend it enough"
United States
jessica c.
The price is £420
includes taxes & fees
12 Nov - 13 Nov
Charming Hudson Valley Escape | Autumn Vibes & Fire Pit

12. Modern cabin retreat

Modern cabin retreat
Catskill
The price is £189
includes taxes & fees
7 Dec - 8 Dec
Modern cabin retreat

13. Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is £200
includes taxes & fees
12 Nov - 13 Nov
Cabin Oasis near Town

14. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is £222
includes taxes & fees
12 Nov - 13 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.

15. Cozy Catskill Escape

Cozy Catskill Escape
Catskill
10.0 out of 10, Exceptional, (2 reviews)
"Very accommodating host. Great with last minute visits."
United States
Kevin P.
The price is £189
includes taxes & fees
30 Nov - 1 Dec
Cozy Catskill Escape

16. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is £462
includes taxes & fees
16 Nov - 17 Nov
Secluded Family Home in Serene Stockbridge Woods

17. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is £215
includes taxes & fees
13 Nov - 14 Nov
Leaf-Peeper Paradise in the Berkshires

18. Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (16 reviews)
"The perfect stay in the Catskills! Everything looked just like the pictures. Clean, easy access to restaurants close by, and Daniel was very easy to communicate with. Highly recommend!"
United States
Amanda
The price is £246
includes taxes & fees
1 Dec - 2 Dec
Modern Luxurious Cabin, Catskills - The Tiny Nook

19. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.2 out of 10, Wonderful, (10 reviews)
"Great property and the host was extremely responsive and helpful."
United States
Robbie S.
The price is £420
includes taxes & fees
12 Nov - 13 Nov
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

20. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is £247
includes taxes & fees
15 Nov - 16 Nov
Home in Great Barrington
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.

Learn more about Chatham

This charming upstate village hosts the Mac-Haydn Theatre's summer productions and a vibrant Main Street with independent shops and cafés. Explore the historic Union Station or time your visit for the Columbia County Fair, a beloved local tradition since 1841.

A brick building with a green dome and columns, labeled "TRACY MEMORIAL VILLAGE HALL".

Top reviews in Chatham