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

Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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 CA $285
CA $490 total
includes taxes & fees
Oct 7 - Oct 8
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.
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 CA $151
CA $202 total
includes taxes & fees
Oct 7 - Oct 8
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 CA $100
CA $290 total
includes taxes & fees
Oct 7 - Oct 8
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 CA $124
CA $322 total
includes taxes & fees
Nov 2 - Nov 3
1800s Carriage house in Berkshires / Hudson Valley
A spacious room with a wooden ceiling, large windows, and a chandelier.

6. Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is CA $606
CA $1,059 total
includes taxes & fees
Oct 7 - Oct 8
Luxury Barn Retreat — All-Season Escape Awaits!
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 CA $371
CA $840 total
includes taxes & fees
Oct 26 - Oct 27
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
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.

8. 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 CA $316
CA $684 total
includes taxes & fees
Oct 14 - Oct 15
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
A two-story house with a balcony, a deck, and a view of the surrounding forest.

9. 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 CA $468
CA $946 total
includes taxes & fees
Oct 18 - Oct 19
Gorgeous Mountain Views Retreat: Family & Nature
A white two-story house with a porch, surrounded by trees and a hill.

10. 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 CA $289
CA $680 total
includes taxes & fees
Oct 7 - Oct 8
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A wooden deck with a wicker sofa, a hammock, and a grill.

11. Larkspire l Catskills Fall Foliage Lake House

Larkspire l Catskills Fall Foliage Lake House
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 CA $392
CA $786 total
includes taxes & fees
Oct 7 - Oct 8
Larkspire l Catskills Fall Foliage Lake House
A modern kitchen with a central island, built-in appliances, and a dining area with a round table.

12. 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 CA $627
CA $1,167 total
includes taxes & fees
Oct 26 - Oct 27
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
A wooden deck leading to a cabin with a window and a door, surrounded by trees.

13. Modern cabin retreat

Modern cabin retreat
Catskill
The price is CA $211
CA $396 total
includes taxes & fees
Oct 27 - Oct 28
Modern cabin retreat
A kitchen with a central island, bar stools, and pendant lighting.

14. 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 CA $183
CA $389 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Catskill Escape
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

15. 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 CA $251
CA $807 total
includes taxes & fees
Oct 9 - Oct 10
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.

16. 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 CA $285
CA $501 total
includes taxes & fees
Oct 21 - Oct 22
Sweet Cozy Victorian in Housatonic. Close to everything.
A staircase with a wooden handrail and a white wall with a light switch.

17. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (28 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 CA $290
CA $451 total
includes taxes & fees
Oct 7 - Oct 8
Leaf-Peeper Paradise in the Berkshires
A modern living space with a kitchen area, a dining table, and a sofa.

18. Cabin Oasis near Town

Cabin Oasis near Town
Catskill
The price is CA $250
CA $448 total
includes taxes & fees
Nov 3 - Nov 4
Cabin Oasis near Town
A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

19. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is CA $449
CA $992 total
includes taxes & fees
Oct 14 - Oct 15
Ellie’s Overlook, best view in the Berkshires!
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, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is CA $317
CA $496 total
includes taxes & fees
Oct 13 - Oct 14
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.
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Top Chatham Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"Loved our stay. Room was nice and clean. Some things a little dated but great for the price!"
Lauren 2-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

Find out more about Chatham

Chatham Vacation Homes information

Number of reviews
311
Accommodation
492 Vacation Homes
Lowest Price
CA $202
Highest Price
CA $1,167

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