A calm lake surrounded by dense evergreen trees and a few deciduous trees with autumn leaves.

East Chatham Vacation Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for East Chatham vacation rentals

A cozy living room with a sofa, a fireplace, and large windows.

1. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
Luxury Barn Near Hudson With New Private Sauna
A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

2. Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (4 reviews)
"This place was better than the photos. Everything was well planned out and extremely comfortable. The host was very attentive with great information about the area. Would definitely recommend."
United States
Lori S.
The price is AED 988
AED 1,259 total
includes taxes & fees
2 Nov - 3 Nov
Sugar Shack - 300 square feet of pure sweetness.
A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

3. BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is AED 988
AED 1,259 total
includes taxes & fees
16 Nov - 17 Nov
BLUSH: Boutique TINY home*private spa*walk to town
A modern building with a wooden deck and a door.

4. 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 AED 1,006
AED 2,333 total
includes taxes & fees
19 Oct - 20 Oct
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,208 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
The price is AED 318
AED 437 total
includes taxes & fees
10 Nov - 11 Nov
Berkshire Mountain Lodge
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

6. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,746 reviews)
"This was a fantastic property to end our New England trip!"
United States
Adrianne
The price is AED 295
AED 370 total
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
A camping setup with a metal chair and a table by a river in a forest.

7. 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, (16 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 AED 735
AED 1,263 total
includes taxes & fees
19 Oct - 20 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

8. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.4 out of 10, Exceptional, (189 reviews)
"Great stay"
United States
George
The price is AED 363
AED 406 total
includes taxes & fees
28 Oct - 29 Oct
Micosta Leisure Inn
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 AED 779
AED 1,772 total
includes taxes & fees
18 Oct - 19 Oct
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

10. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (8 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is AED 1,021
AED 2,109 total
includes taxes & fees
27 Oct - 28 Oct
NEW RENO Historic Creamery in Berkshires w/hot tub
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

11. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is AED 823
AED 2,035 total
includes taxes & fees
28 Oct - 29 Oct
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Miscellaneous

12. 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 AED 257
AED 756 total
includes taxes & fees
18 Oct - 19 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
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.

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

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is AED 1,157
AED 2,538 total
includes taxes & fees
25 Oct - 26 Oct
Ellie’s Overlook, best view in the Berkshires!
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

14. 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, (8 reviews)
"A lovely house! Very convenient for a Tanglewood weekend."
United States
Robert B.
The price is AED 646
AED 2,059 total
includes taxes & fees
18 Oct - 19 Oct
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

15. 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 AED 1,253
AED 2,372 total
includes taxes & fees
20 Oct - 21 Oct
Secluded Family Home in Serene Stockbridge Woods
A sign for The Stephentown Hotel with a depiction of a red building and mountains.

16. 2 Bed Berkshire Getaway @ Stephentown Hotel

2 Bed Berkshire Getaway @ Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (7 reviews)
"This place is amazing! It is so clean and updated with lots of amenities! Lots of arcade games in the apartment thatthe whole family enjoyed! It's a quick trip to jimney peak to ski it's just down the road. Great restaurants nearby. Definitely recommend this place."
United States
elizabeth r.
The price is AED 513
AED 1,126 total
includes taxes & fees
18 Oct - 19 Oct
2 Bed Berkshire Getaway @ Stephentown Hotel
A wooden deck with a staircase leading to a covered porch area.

17. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (64 reviews)
"The room was sufficient to our needs. Didn’t realize it was a multi-unit property or that it was on the second floor."
United States
Douglas
The price is AED 360
AED 486 total
includes taxes & fees
20 Oct - 21 Oct
All comforts of home
A two-story house with a balcony, a deck, and a view of the surrounding forest.

18. 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 AED 1,058
AED 2,217 total
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
A wooden deck with a staircase leading to a covered porch area.

19. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"No frills, very clean and peaceful, beautiful setting"
United States
Lori M.
The price is AED 390
AED 519 total
includes taxes & fees
19 Oct - 20 Oct
All the comforts of home
A patio with stone flooring, wicker chairs, and a red umbrella. A lake with a dock and a small boat is visible in the background.

20. A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!

A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
Averill Park
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful family weekend at the lake house. Beautiful place to stay. Perfect for a family gathering."
United States
KenD
The price is AED 1,339
AED 2,942 total
includes taxes & fees
18 Oct - 19 Oct
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
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 East Chatham Hotel Reviews

Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

10/10 Excellent
"Excellent stay."
Napoleon 2-night trip
Posted 8 hours ago
Country Inn & Suites by Radisson, Downtown Albany New York

Frequently asked questions

Can I find a vacation rental in East Chatham?

Yes, we have vacation rentals close to popular local attractions in East Chatham, or you can select a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that East Chatham has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental outside of East Chatham is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in East Chatham?

Expedia has 7 vacation rentals for your stay in East Chatham.

What can I see and do in East Chatham?

Meizinger Lake and Hand Hollow Conservation Area are a couple of lovely local spots to get outside and enjoy nature. Hand Hollow State Forest and Kinderhook Lake are a couple of places you'll find in the larger area.

What are vacation rentals like in East Chatham?

Vacation rentals are privately owned properties you can stay in for several days or longer in East Chatham. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.