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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 543 Vacation Homes in East Chatham with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (245)
"What a great spot to stay for the few days we were there Can’t wait to come back! "
The price is AED 551
AED 837 total
includes taxes & fees
13 May - 14 May
Berkshire Village Carriage House - Super Private!!
Hancock Village Inn at Jiminy Peak
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is AED 2,016
AED 3,810 total
includes taxes & fees
12 May - 13 May
Hancock Village Inn at Jiminy Peak
Romantic Villa
Fridge, microwave, oven, stovetop

Romantic Villa

10.0 out of 10, Exceptional, (21)
"Great stay exceeded expectations"
Romantic Villa
Spectacular views and close to Great Barrington.
Smart TV, fireplace

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Lakeside Oasis Just You, The Lake & The View!
Exterior

Lakeside Oasis Just You, The Lake & The View!

9.8 out of 10, Exceptional, (70)
"Perfect location for a peaceful, scenic vacation."
Lakeside Oasis Just You, The Lake & The View!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (25)
"Well located and comfortable "
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
TV, fireplace, books

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

9.0 out of 10, Wonderful, (22)
"We had a great time staying at this house. It was quiet and relaxing. We would stay again!"
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
Secluded Lux Mansion Pool Home with Amazing Views
Fridge, microwave, oven, stovetop

Secluded Lux Mansion Pool Home with Amazing Views

10.0 out of 10, Exceptional, (1)
"We had a great time staying in the house for the weekend as a group of 10. Kitchen and bathrooms are well-stocked. The living room couch is enormous. All of the bedrooms are bright and cozy. The views and property are absolutely stunning. Had we been fewer, we probably would have used the outdoor firepits. Barry and Alisha are lovely and helpful hosts -- they sent along a great list of food reccs ahead of time, responded quickly when I couldn't find a few things, etc. "
Secluded Lux Mansion Pool Home with Amazing Views
Heart of Lenox Walk to Town Cozy Cottage!
Fridge, microwave, oven, stovetop

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (71)
"Going to the Berkshires this is a great place to stay. It is within walking distance to over 8 restaurants in downtown Lenox. Great gas stove and comfortable bed. Owner makes sure your stay is great. Would stay here again. "
Heart of Lenox Walk to Town Cozy Cottage!
Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi
Outdoor pool, a heated pool

Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

10.0 out of 10, Exceptional, (47)
"We had the most wonderful time! The views are unbelievable - sitting in the pool or hot tub or around the fire pit, watching the barges sail by was so special! We can’t wait to come back!"
Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Fridge, microwave, oven, stovetop

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (24)
"Great house that has everything for the family vacation "
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
The Race Mountain House
Pool

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"
The Race Mountain House
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (36)
"The property was centrally located for skiing, and was a comfortable stay."
The price is AED 687
AED 1,621 total
includes taxes & fees
13 May - 14 May
Cheerful 3-bedroom cottage with woodstove
Perfect Nature Haven In Great Barrington
Exterior

Perfect Nature Haven In Great Barrington

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."
Perfect Nature Haven In Great Barrington
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Property grounds

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (4)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Mountain Blossom Retreat by Evergreen Home
A heated pool

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"Lovely ski weekend! Best memory: hot tubbing at sunset after skiing with snow falling all around! "
Mountain Blossom Retreat by Evergreen Home
4 Bdrm Modern Victorian with Tree House and playground
Terrace/patio

4 Bdrm Modern Victorian with Tree House and playground

9.8 out of 10, Exceptional, (110)
"Great house"
4 Bdrm Modern Victorian with Tree House and playground
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Terrace/patio

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (9)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Exclusive Estate, Heated Yearround Outdoor Pool
Fridge, microwave, oven, stovetop

Exclusive Estate, Heated Yearround Outdoor Pool

9.6 out of 10, Exceptional, (19)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
Exclusive Estate, Heated Yearround Outdoor Pool
Quintessential 6-BR Berkshires Lodge
Exterior

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge
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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Other property types in East Chatham

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1804)
"The property was clean and the staff very accommodated."
The price is AED 403
AED 490 total
includes taxes & fees
11 May - 12 May
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (929)
"Out dated not many resort like options "
The price is AED 488
AED 545 total
includes taxes & fees
11 May - 12 May
Jiminy Peak Mountain Resort
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (96)
"Third or fourth time staying. Always a pleasure "
The price is AED 477
AED 515 total
includes taxes & fees
27 May - 28 May
Micosta Leisure Inn
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.