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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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, (4 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is ￥60,569
￥98,697 total
includes taxes & fees
Nov 8 - Nov 9
Luxury Barn Near Hudson With New Private Sauna
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 ￥44,021
￥96,124 total
includes taxes & fees
Nov 18 - Nov 19
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Exterior

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,257 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is ￥12,154
￥17,114 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Mountain Lodge
Indoor pool

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,830 reviews)
"Great resort, great location very spacious."
United States
Marcos
The price is ￥12,722
￥15,948 total
includes taxes & fees
Nov 8 - Nov 9
Vacation Village in the Berkshires
Exterior

5. 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 ￥31,670
￥51,787 total
includes taxes & fees
Nov 9 - Nov 10
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

6. 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 ￥41,013
￥49,841 total
includes taxes & fees
Nov 16 - Nov 17
Sugar Shack - 300 square feet of pure sweetness.
A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

7. 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 ￥41,013
￥50,018 total
includes taxes & fees
Nov 10 - Nov 11
BLUSH: Boutique TINY home*private spa*walk to town
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

8. 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)
"It was a great stay! Centrally located in the Berkshire, very comfortable beds, amazing amenities!"
United States
Molly K.
The price is ￥46,872
￥89,158 total
includes taxes & fees
Nov 9 - Nov 10
NEW RENO Historic Creamery in Berkshires w/hot tub
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

9. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (195 reviews)
"Great stay"
United States
George
The price is ￥15,631
￥17,507 total
includes taxes & fees
Nov 9 - Nov 10
Micosta Leisure Inn
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 ￥27,078
￥65,829 total
includes taxes & fees
Nov 9 - Nov 10
1789 Shaker Farmhouse in Berkshires/Hudson Valley
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 ￥40,221
￥93,024 total
includes taxes & fees
Nov 8 - Nov 9
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

12. 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 ￥11,085
￥30,986 total
includes taxes & fees
Nov 7 - Nov 8
NEW RENO - Chalet-style farm loft near Tanglewood
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

13. 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 ￥32,145
￥87,884 total
includes taxes & fees
Nov 9 - Nov 10
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A room with a large window, two sofas, and a small table.

14. Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
Richmond
The price is ￥142,499
￥198,877 total
includes taxes & fees
Nov 12 - Nov 13
Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
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 ￥54,013
￥97,301 total
includes taxes & fees
Nov 9 - Nov 10
Secluded Family Home in Serene Stockbridge Woods
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.

16. 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 ￥47,030
￥108,801 total
includes taxes & fees
Nov 9 - Nov 10
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
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, (65 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 ￥15,534
￥19,524 total
includes taxes & fees
Nov 9 - Nov 10
All comforts of home
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

18. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is ￥14,806
￥35,116 total
includes taxes & fees
Nov 8 - Nov 9
Berkshires Apartment at the Stephentown Hotel
A backyard with a fire pit, wooden deck, and string lights.

19. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (4 reviews)
"Enjoyed our 2 night stay, everything was clean and worked smoothly. The hot tub and couch were the favorites, also enjoyed the coffee maker very much. Would highly recommended staying here!"
United States
Ross O.
The price is ￥29,611
￥54,801 total
includes taxes & fees
Nov 10 - Nov 11
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
A wooden deck with a staircase leading to a covered porch area.

20. 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 ￥16,817
￥20,964 total
includes taxes & fees
Nov 8 - Nov 9
All the comforts of home
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Very centrally located. Right next to a good little market. Very reasonable price for an apartment like room."
Holly 3-night trip
Posted 2 hours ago
Berkshire Mountain Lodge

Find out more about East Chatham

Search for holiday rentals in East Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in East Chatham using one of the methods below:

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Look no further and take a look at our great range of rental properties in East Chatham!

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.