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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (15 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 ￥31,474
￥53,758 total
includes taxes & fees
Oct 1 - Oct 2
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 ￥40,444
￥95,882 total
includes taxes & fees
Oct 5 - Oct 6
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, (37 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is ￥16,713
￥22,245 total
includes taxes & fees
Oct 1 - Oct 2
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)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is ￥11,016
￥32,557 total
includes taxes & fees
Oct 1 - Oct 2
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

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 ￥14,321
￥36,214 total
includes taxes & fees
Oct 28 - Oct 29
1800s Carriage house in Berkshires / Hudson Valley
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.

6. 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 ￥34,936
￥75,221 total
includes taxes & fees
Oct 14 - Oct 15
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
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, (10 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 ￥40,927
￥92,029 total
includes taxes & fees
Oct 19 - Oct 20
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

8. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (27 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 ￥31,867
￥49,834 total
includes taxes & fees
Oct 6 - Oct 7
Riverside Retreat in the Berkshires
A white two-story house with a porch, surrounded by trees and a hill.

9. 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 ￥37,936
￥81,394 total
includes taxes & fees
Oct 4 - Oct 5
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A modern interior with a staircase, wooden flooring, a dining area, and a brick wall.

10. Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (30 reviews)
"Great little place to stay at right in downtown!!"
United States
Bryan S.
Catskill Cottage Walk to Downtown & River Views
A cabin with a large deck, multiple windows, and a fire pit.

11. Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (12 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 ￥25,651
￥54,217 total
includes taxes & fees
Oct 28 - Oct 29
Modern Luxurious Cabin, Catskills - The Tiny Nook
A modern living space with a kitchen area, a dining table, and a sofa.

12. Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is ￥22,982
￥44,195 total
includes taxes & fees
Oct 6 - Oct 7
Cabin Oasis near Town
A modern kitchen with a central island, built-in appliances, and a dining area with a round table.

13. 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 ￥62,319
￥118,443 total
includes taxes & fees
Oct 13 - Oct 14
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
A two-story house with a balcony, a deck, and a view of the surrounding forest.

14. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (134 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is ￥62,964
￥117,239 total
includes taxes & fees
Oct 18 - Oct 19
Gorgeous Mountain Views Retreat: Family & Nature
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

15. 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)
"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 ￥31,474
￥55,372 total
includes taxes & fees
Oct 20 - Oct 21
Sweet Cozy Victorian in Housatonic. Close to everything.
A wooden deck leading to a cabin with a window and a door, surrounded by trees.

16. Modern cabin retreat

Modern cabin retreat
Catskill
The price is ￥23,448
￥44,007 total
includes taxes & fees
Oct 5 - Oct 6
Modern cabin retreat
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
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 ￥46,955
￥92,361 total
includes taxes & fees
Oct 6 - Oct 7
Larkspire I Sleepy Hollow Lake I Beach & Firepit
A kitchen with a central island, bar stools, and pendant lighting.

18. 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 ￥20,143
￥42,603 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Catskill Escape
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is ￥27,697
￥88,214 total
includes taxes & fees
Oct 6 - Oct 7
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Cook, gather, and connect with a central island

20. Catskill * Screened Porch * Chef’s Kitchen

Catskill * Screened Porch * Chef’s Kitchen
Catskill
10.0 out of 10, Exceptional, (1 review)
"As described."
United States
kimberly j.
The price is ￥28,043
￥115,273 total
includes taxes & fees
Oct 5 - Oct 6
Catskill * Screened Porch * Chef’s Kitchen
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

Berkshires Untold

Berkshires Untold

8/10 Good
"A very good place to stay"
Madhavi R 1-night trip
Posted 18 hours ago
Berkshires Untold

Find out more about Chatham

Chatham Vacation Homes information

Number of reviews
310
Accommodation
502 Vacation Homes
Lowest Price
￥22,245
Highest Price
￥118,443