A city street with buildings, parked cars, and solar panels.

Search Vacation Homes in Chatham

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Chatham vacation 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, (12 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is ￥31,790
￥54,653 total
includes taxes & fees
Sep 20 - Sep 21
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, (4 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 ￥39,579
￥96,489 total
includes taxes & fees
Sep 13 - Sep 14
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, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is ￥16,880
￥22,467 total
includes taxes & fees
Aug 26 - Aug 27
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
8.6 out of 10, Excellent, (7 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 ￥11,127
￥33,240 total
includes taxes & fees
Aug 25 - Aug 26
NEW RENO - Chalet-style farm loft near Tanglewood
A modern interior with a staircase, wooden flooring, a dining area, and a brick wall.

5. Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (27 reviews)
"Great little place to stay at right in downtown!!"
United States
Bryan S.
Catskill Cottage Walk to Downtown & River Views
A spacious living room with a dining area, a kitchen, and a large window.

6. 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 ￥15,259
￥38,084 total
includes taxes & fees
Sep 14 - Sep 15
1800s Carriage house in Berkshires / Hudson Valley
A couple in a hot tub with a natural landscape in the background.

7. 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, (8 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 ￥56,427
￥109,841 total
includes taxes & fees
Aug 25 - Aug 26
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
A group of people seated around a table outdoors with a view of a backyard and houses in the background.

8. 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’
10.0 out of 10, Exceptional, (1 review)
"We were only there for one night, but we really liked this space - it was clean and the beds were so comfortable! Thanks so much to our host for opening his home to us."
United States
Rachel P.
The price is ￥33,538
￥55,187 total
includes taxes & fees
Aug 31 - Sep 1
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

9. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 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 ￥30,399
￥47,273 total
includes taxes & fees
Sep 22 - Sep 23
Cozy Riverside Berkshires Retreat
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

10. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is ￥27,975
￥90,334 total
includes taxes & fees
Aug 29 - Aug 30
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 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 ￥27,816
￥50,778 total
includes taxes & fees
Sep 1 - Sep 2
Sweet Cozy Victorian in Housatonic. Close to everything.
A white two-story house with a porch, surrounded by trees and a hill.

12. 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 ￥41,009
￥86,316 total
includes taxes & fees
Sep 9 - Sep 10
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A spacious kitchen with a central island, wooden flooring, and large windows.

13. Cozy Catskill Escape

Cozy Catskill Escape
Catskill
10.0 out of 10, Exceptional, (1 review)
"Inside the cabin was fantastic! Modern, clean, well stocked with essentials. We very much enjoyed our time in the cabin. The town was so charming and fun to explore. Was not expecting the auto/junk yard atmosphere on the outside. I understand why it wasn’t part of the description of the property. That being said, the neighbors did not bother us during our stay."
United States
Vicki M.
The price is ￥21,140
￥44,232 total
includes taxes & fees
Sep 7 - Sep 8
Cozy Catskill Escape
A wooden deck leading to a cabin with a window and a door, surrounded by trees.

14. Modern cabin retreat

Modern cabin retreat
Catskill
The price is ￥22,730
￥43,667 total
includes taxes & fees
Sep 15 - Sep 16
Modern cabin retreat
A modern living space with a kitchen area, a dining table, and a sofa.

15. Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is ￥24,796
￥48,060 total
includes taxes & fees
Sep 15 - Sep 16
Cabin Oasis near Town
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.

16. Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
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 ￥39,579
￥81,904 total
includes taxes & fees
Sep 23 - Sep 24
Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
A wooden deck with a wicker sofa, a hammock, and a grill.

17. Larkspire I Sleepy Hollow Lake I Beach & Firepit

Larkspire I Sleepy Hollow Lake I Beach & Firepit
Athens
The price is ￥38,204
￥82,459 total
includes taxes & fees
Sep 22 - Sep 23
Larkspire I Sleepy Hollow Lake I Beach & Firepit
A living room with a brown leather sofa, two grey armchairs, a glass coffee table, and a wooden side table with a lamp.

18. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.2 out of 10, Wonderful, (5 reviews)
The price is ￥25,321
￥60,775 total
includes taxes & fees
Sep 23 - Sep 24
stylish Berkshires Retreat
A modern kitchen with a central island, built-in appliances, and a dining area with a round table.

19. 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 ￥69,938
￥130,136 total
includes taxes & fees
Sep 7 - Sep 8
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

20. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥42,917
￥64,628 total
includes taxes & fees
Aug 25 - Aug 26
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chatham Hotel Reviews

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

10/10 Excellent
"Great spa"
Elizabeth 2-night trip
Posted 2 hours ago
Pocketbook Hotel and Bath

Find out more about Chatham

Chatham Vacation Homes information

Number of reviews
149
Accommodation
502 Vacation Homes
Lowest Price
￥22,467
Highest Price
￥130,136