Search Vacation Homes in East Chatham

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Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for East Chatham vacation homes

Property grounds
All the comforts of home

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (28)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
$126 nightly
The price is $141
Dec 11 - Dec 12
Total with taxes and fees
All the comforts of home
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
$207 nightly
The price is $231
Dec 15 - Dec 16
Total with taxes and fees
Home in Great Barrington
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
$215 nightly
The price is $240
Dec 11 - Dec 12
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
$416 nightly
The price is $465
Jan 10 - Jan 11, 2026
Total with taxes and fees
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Property grounds
Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking

Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking

Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking
2.0 star property
Albany
8.0 out of 10, Very Good, (1)
"Overall nice stay "
United States
Anonymous traveler
$223 nightly
The price is $241
Dec 11 - Dec 12
Total with taxes and fees
Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking
Exterior
Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam
Hillsdale
8.4 out of 10, Very Good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
United States
Stefanie K.
$479 nightly
The price is $537
Dec 11 - Dec 12
Total with taxes and fees
Perfect House In Hillsdale, Brings Friends & Fam
Fridge, microwave, oven, stovetop
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
$433 nightly
The price is $484
Dec 12 - Dec 13
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$398 nightly
The price is $445
Dec 14 - Dec 15
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Property grounds
Modern & Cozy Cntr Square Townhouse Gem from 1854

Modern & Cozy Cntr Square Townhouse Gem from 1854

Modern & Cozy Cntr Square Townhouse Gem from 1854
Albany
10.0 out of 10, Exceptional, (62)
"Great stay, thank you"
United States
Olga K.
$249 nightly
The price is $269
Dec 11 - Dec 12
Total with taxes and fees
Modern & Cozy Cntr Square Townhouse Gem from 1854
Terrace/patio
Treat yourself at the stunning June Farms Wellness Huts!

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)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
United States
SteveS
$430 nightly
The price is $478
Dec 15 - Dec 16
Total with taxes and fees
Treat yourself at the stunning June Farms Wellness Huts!
Fridge, microwave, oven, stovetop
Modern and Cozy Pine Hills Home from Early 1900s

Modern and Cozy Pine Hills Home from Early 1900s

Modern and Cozy Pine Hills Home from Early 1900s
Pine Hills
10.0 out of 10, Exceptional, (56)
"This was an excellent stay! Clean, comfortable, and responsive hosts. Will stay again if back in that area. "
United States
Amy S.
$232 nightly
The price is $251
Dec 16 - Dec 17
Total with taxes and fees
Modern and Cozy Pine Hills Home from Early 1900s
Fridge, microwave, oven, stovetop
Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape
2.0 star property
Stottville
$300 nightly
The price is $304
Dec 11 - Dec 12
Total with taxes and fees
Hudson Hot Tub & Pet Escape
Outdoor dining
“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

“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany
Pine Hills
10.0 out of 10, Exceptional, (1)
"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.
$397 nightly
The price is $429
Dec 14 - Dec 15
Total with taxes and fees
“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany
Outdoor spa tub
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Valatie
10.0 out of 10, Exceptional, (58)
"Great spot on the lake. Super quiet and relaxing."
United States
vincent m.
$477 nightly
The price is $534
Dec 11 - Dec 12
Total with taxes and fees
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Exterior
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (72)
"We had a wonderful stay, thank you! "
United States
Gary L.
$488 nightly
The price is $545
Dec 11 - Dec 12
Total with taxes and fees
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Living area
Charming 3-bedroom house with pool table

Charming 3-bedroom house with pool table

Charming 3-bedroom house with pool table
Pine Hills
7.6 out of 10, Good, (4)
"We had a great stay as we played one night at the Empire. The house is very quaint and there is ample shared parking in the back. If ever we come back to Albany, I'll be sure to consider this house. "
United States
Chiqui R.
$367 nightly
The price is $396
Dec 14 - Dec 15
Total with taxes and fees
Charming 3-bedroom house with pool table
Private kitchen
Honey Comb Hideout 3Br. House Albany

Honey Comb Hideout 3Br. House Albany

Honey Comb Hideout 3Br. House Albany
Albany
$514 nightly
The price is $555
Dec 11 - Dec 12
Total with taxes and fees
Honey Comb Hideout 3Br. House Albany
Game room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington
Great Barrington
9.4 out of 10, Exceptional, (6)
$253 nightly
The price is $283
Dec 16 - Dec 17
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington
Property grounds
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!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (29)
"Great stay in a well appointed house close to trails, Stockbridge center, and a quick car trip to Lenox, Great Barrington, Tanglewood, Jacobs Pillow, and Shakespeare & Co. we enjoyed the morning walks, coffee at the Lost Lamb, drinks at the Red Lion Inn, dance at Jacob’s Pillow, music at Tanglewood, ice cream at High Lawn Farm, and just that Berkshire vibe! "
United States
Phillip F.
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Outdoor pool, a heated pool
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
Hudson
9.8 out of 10, Exceptional, (27)
"Met our son and his girls for a little getaway. Very cool house complete with lots to do! Thank you. Hope to get to experience it during the summer months sometime."
United States
Kathy M.
$973 nightly
The price is $1,099
Dec 11 - Dec 12
Total with taxes and fees
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Really quiet, peaceful stay and beautiful spot for the money. Front desk staff so nice. No elevator to second floor so keep in mind if have accessibility issues/wheelchair user. Great view and gluten free menu options. Would stay again if in area. Was just passing through on way to medical appointment. "
Meaghan 1-night trip
Posted 1 day ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about East Chatham

East Chatham Vacation Homes information

Number of reviews
429
Accommodation
510 Vacation Homes
Lowest Price
$141
Highest Price
$1,099

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