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

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for East Chatham holiday homes

Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is £376
includes taxes & fees
13 Jul - 14 Jul
Cheerful 3-bedroom cottage with woodstove
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (18 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 £245
includes taxes & fees
14 Jul - 15 Jul
Cozy Riverside Berkshires Retreat
Property grounds

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (9 reviews)
"Great experience! Only there for one night because our son had a wrestling tournament. Wish we would have had more time at property. "
United States
Rochelle F.
The price is £285
includes taxes & fees
13 Jul - 14 Jul
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (7 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 £255
includes taxes & fees
13 Jul - 14 Jul
Sweet Cozy Victorian in Housatonic. Close to everything.
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (34 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is £295
includes taxes & fees
19 Jul - 20 Jul
Home in Great Barrington
Terrace/patio

Sleepy Hollow Lake Home w/ Deck, Pool Access!

Sleepy Hollow Lake Home w/ Deck, Pool Access!
Athens
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful property that was clean. Hosts left information about surrounding area and restaurants- we definitely felt welcomed when we arrived. Beautiful area with lots to do! Would stay here again"
United States
Sarah M.
The price is £441
includes taxes & fees
19 Jul - 20 Jul
Sleepy Hollow Lake Home w/ Deck, Pool Access!
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (39 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is £816
includes taxes & fees
19 Jul - 20 Jul
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
TV, fireplace, printers

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (6 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is £991
includes taxes & fees
13 Jul - 14 Jul
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Fridge, microwave, oven, stovetop

Perfect 4-bedroom house with AC in tranquil Albany

Perfect 4-bedroom house with AC in tranquil Albany
Delaware Avenue
10.0 out of 10, Exceptional, (2 reviews)
"The place so clean and beautiful we enjoyed the game refreshed my boy time memories and space and rooms so unique. I will definitely recommend that place then hotel. It’s more than five stars hotel."
United States
Alex
The price is £401
includes taxes & fees
20 Jul - 21 Jul
Perfect 4-bedroom house with AC in tranquil Albany
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is £510
includes taxes & fees
13 Jul - 14 Jul
Treetop Hideaway in Tyringham
Terrace/patio

“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany

“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany
Pine Hills
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay at this property and will rent again when in the area. The owners were very responsive and great to work with. The apt was beautiful and immaculate. We enjoyed our stay very much. The only area that was perfect was the outside stairs to the front door— uneven, steep, etc. We had older guest with us and this was concerning. But we managed. Thanks again for a great stay"
United States
Melissa A.
The price is £324
includes taxes & fees
19 Jul - 20 Jul
“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany
Outdoor dining

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is £809
includes taxes & fees
14 Jul - 15 Jul
Hancock Village Inn Near Jiminy Peak
Interior

Downtown 3BR duplex full kitchen parking off i-787

Downtown 3BR duplex full kitchen parking off i-787
Arbor Hill
10.0 out of 10, Exceptional, (6 reviews)
"Arbor Hill is beautiful, well kept & comfortable! The host went above & beyond to accommodate us, they even showed up in the morning with delicious baked goods! You could not ask for a better place to stay, I highly recommend! "
United States
Stephanie B.
The price is £234
includes taxes & fees
13 Jul - 14 Jul
Downtown 3BR duplex full kitchen parking off i-787
Fridge, microwave, oven, stovetop

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 £523
includes taxes & fees
20 Jul - 21 Jul
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Smart TV, books

Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
8.0 out of 10, Very good, (1 review)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is £499
includes taxes & fees
13 Jul - 14 Jul
Spacious Central Berkshires Home for Groups
Lobby

Modern Designer Chalet on 5.5 Private Acres Near Tanglewood

Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
West Stockbridge
10.0 out of 10, Exceptional, (5 reviews)
"The home was great! It was tucked away but still very close to everything! Our family enjoyed our stay and Michelle was very welcoming and had everything at the house for us to feel comfortable."
United States
Jon U.
The price is £808
includes taxes & fees
16 Jul - 17 Jul
Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
Terrace/patio

Treat yourself at the stunning June Farms Wellness Huts!

Treat yourself at the stunning June Farms Wellness Huts!
West Sand Lake
10.0 out of 10, Exceptional, (8 reviews)
"Loved the wellness hut. Our sauna didnt work however the room was spacious and comfy. The staff is very attentive and we also enjoyed the soup stroll. Would def recommend."
United States
Lauren C.
The price is £422
includes taxes & fees
6 Aug - 7 Aug
Treat yourself at the stunning June Farms Wellness Huts!
Fridge, microwave, stovetop, dishwasher

Berkshire House Stay: 5BR/5BA

Berkshire House Stay: 5BR/5BA
Lee
10.0 out of 10, Exceptional, (22 reviews)
"Wonderful stay, beautiful, well equipped and clean property. Highly recommend for an adult famiky getaway "
United States
jennifer r.
The price is £828
includes taxes & fees
13 Jul - 14 Jul
Berkshire House Stay: 5BR/5BA
Fridge, microwave, stovetop, dishwasher

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.6 out of 10, Exceptional, (4 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is £423
includes taxes & fees
13 Jul - 14 Jul
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Exterior

Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (129 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 £499
includes taxes & fees
9 Aug - 10 Aug
Gorgeous Mountain Views Retreat: Family & Nature
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"The place was as advertised. It was clean and comfortable."
Jacqueline 2-night trip
Posted 1 hour ago
Vacation Village in the Berkshires

Find out more about East Chatham

East Chatham Holiday Homes information

Number of reviews
10,288
Accommodation
527 Holiday Homes
Lowest Price
£48
Highest Price
£203