Holiday Homes in Chatham

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Find holiday rentals that suit your style

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Cabins
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Apartments
Apartments

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Chatham holiday homes

A camping setup with a metal chair and a table by a river in a forest.

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 NZ$586
includes taxes & fees
15 Nov - 16 Nov
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A modern building with a wooden deck and a door.

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 NZ$1,032
includes taxes & fees
30 Nov - 1 Dec
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A wooden deck with a staircase leading to a covered porch area.

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 NZ$240
includes taxes & fees
16 Nov - 17 Nov
All the comforts of home
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

4. 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 NZ$354
includes taxes & fees
16 Nov - 17 Nov
NEW RENO - Chalet-style farm loft near Tanglewood
A single-story white house with a dark roof, a front door, and a small porch with a bench.

5. 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 NZ$383
includes taxes & fees
16 Nov - 17 Nov
1800s Carriage house in Berkshires / Hudson Valley
A spacious living room with wooden beams, large windows, a chandelier, and a fireplace.

6. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is NZ$1,133
includes taxes & fees
18 Nov - 19 Nov
Luxury Barn Near Hudson With New Private Sauna
A white two-story house with a porch, surrounded by trees and a hill.

7. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (6 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 NZ$724
includes taxes & fees
16 Nov - 17 Nov
1789 Shaker Farmhouse in Berkshires/Hudson Valley
An outdoor patio with a fire pit, wooden deck, and string lights.

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 NZ$1,283
includes taxes & fees
16 Nov - 17 Nov
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

9. 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 NZ$546
includes taxes & fees
16 Nov - 17 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.
A wooden deck with a wicker sofa, a hammock, and a grill.

10. 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 NZ$993
includes taxes & fees
15 Nov - 16 Nov
Modern Family Home · Walk to Lake · Firepit
A wooden cabin with a door open to a sandy beach, a sign reading "Ditch House," and a view of a lake and forest in the background.

11. 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 NZ$787
includes taxes & fees
18 Nov - 19 Nov
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
A wooden deck leading to a house with a dark exterior and white windows.

12. Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is NZ$481
includes taxes & fees
16 Nov - 17 Nov
Cabin Oasis near Town
A two-story house with a central door, two windows on each side, and a pathway leading to the entrance.

13. 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 NZ$434
includes taxes & fees
1 Dec - 2 Dec
Cozy Catskill Escape
A modern living space with a wooden ceiling, a flat-screen TV, a sofa, and a small table.

14. Modern cabin retreat

Modern cabin retreat
Catskill
The price is NZ$460
includes taxes & fees
16 Nov - 17 Nov
Modern cabin retreat
A picnic table in a grassy yard with trees and a fence in the background.

15. A Cozy Berkshire Escape l Close to the Slopes

A Cozy Berkshire Escape l Close to the Slopes
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 NZ$539
includes taxes & fees
16 Nov - 17 Nov
A Cozy Berkshire Escape l Close to the Slopes
A covered porch with string lights, a ceiling fan, and outdoor seating.

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 NZ$1,080
includes taxes & fees
16 Nov - 17 Nov
Secluded Family Home in Serene Stockbridge Woods
A cabin with a wooden deck, a large window, and a black exterior wall.

17. 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 NZ$610
includes taxes & fees
30 Nov - 1 Dec
Modern Luxurious Cabin, Catskills - The Tiny Nook
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

18. 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 NZ$1,009
includes taxes & fees
7 Dec - 8 Dec
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A modern living room with a sectional sofa, wooden beams, a large window, and a view of the outdoors.

19. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires
West Stockbridge
The price is NZ$2,234
includes taxes & fees
30 Nov - 1 Dec
Beautiful and Private Home Centrally Located in the Berkshires
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden ceiling.

20. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is NZ$1,089
includes taxes & fees
22 Nov - 23 Nov
Fantastic 2-bedroom house with AC in quaint Hillsdale.
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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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.

See all hotels in Chatham
A brick building with a green dome and columns, labeled "TRACY MEMORIAL VILLAGE HALL".

Top reviews in Chatham

A hallway with a staircase, a framed painting, a mirror, and a potted plant.
Howard Hotel

Howard Hotel

Howard Hotel
Hudson

10/10 Excellent

Excellent property in a great location. Staff were very responsive and helpful. One tip, is that if you are arriving before checkin, speak to staff before your arrival and they will help you sort out somewhere to leave your bags.
Australia
Tom
Reviewed September 22, 2026
Howard Hotel