Search Vacation Homes in East Chatham

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Check prices for these dates

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

Our top choices for East Chatham vacation homes

Property grounds
All the comforts of home

Vacation Home in 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.
The price is AED 390
AED 519 total
includes taxes & fees
11 Dec - 12 Dec
All the comforts of home
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
The price is AED 479
AED 847 total
includes taxes & fees
15 Dec - 16 Dec
Home in Great Barrington
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Vacation Home in 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.
The price is AED 496
AED 886 total
includes taxes & fees
18 Dec - 19 Dec
Sweet Cozy Victorian in Housatonic. Close to everything.
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Vacation Home in Lebanon Springs

8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is AED 496
AED 1,366 total
includes taxes & fees
11 Dec - 12 Dec
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Property grounds
Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking

Vacation Home in Albany

2.0 star property
8.0 out of 10, Very Good, (1)
"Overall nice stay "
United States
Anonymous traveler
The price is AED 551
AED 885 total
includes taxes & fees
11 Dec - 12 Dec
Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking
Exterior
Perfect House In Hillsdale, Brings Friends & Fam

Vacation Home in 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.
The price is AED 683
AED 1,971 total
includes taxes & fees
11 Dec - 12 Dec
Perfect House In Hillsdale, Brings Friends & Fam
Fridge, microwave, oven, stovetop
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Vacation Home in Pittsfield

2.0 star property
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is AED 988
AED 1,810 total
includes taxes & fees
11 Dec - 12 Dec
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Property grounds
Cheerful 3-bedroom cottage with woodstove

Vacation Home in Sheffield

10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 724
AED 1,666 total
includes taxes & fees
15 Dec - 16 Dec
Cheerful 3-bedroom cottage with woodstove
Property grounds
Modern & Cozy Cntr Square Townhouse Gem from 1854

Vacation Home in Albany

10.0 out of 10, Exceptional, (62)
"Great stay, thank you"
United States
Olga K.
The price is AED 592
AED 992 total
includes taxes & fees
11 Dec - 12 Dec
Modern & Cozy Cntr Square Townhouse Gem from 1854
Terrace/patio
Treat yourself at the stunning June Farms Wellness Huts!

Vacation Home in 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
The price is AED 1,011
AED 1,755 total
includes taxes & fees
15 Dec - 16 Dec
Treat yourself at the stunning June Farms Wellness Huts!
Fridge, microwave, oven, stovetop
Modern and Cozy Pine Hills Home from Early 1900s

Vacation Home in 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.
The price is AED 549
AED 938 total
includes taxes & fees
16 Dec - 17 Dec
Modern and Cozy Pine Hills Home from Early 1900s
Fridge, microwave, oven, stovetop
Hudson Hot Tub & Pet Escape

Vacation Home in Stottville

2.0 star property
The price is AED 529
AED 1,115 total
includes taxes & fees
16 Dec - 17 Dec
Hudson Hot Tub & Pet Escape
Outdoor dining
“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany

Vacation Home in 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.
The price is AED 658
AED 1,607 total
includes taxes & fees
14 Dec - 15 Dec
“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!!!

Vacation Home in Valatie

10.0 out of 10, Exceptional, (58)
"Great spot on the lake. Super quiet and relaxing."
United States
vincent m.
The price is AED 992
AED 1,962 total
includes taxes & fees
11 Dec - 12 Dec
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Exterior
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Vacation Home in Hancock

9.8 out of 10, Exceptional, (72)
"Great communication. Lots of games for the kids. Comfortable beds. Great living and game room. "
United States
Samuel R.
The price is AED 970
AED 2,010 total
includes taxes & fees
11 Dec - 12 Dec
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Living area
Charming 3-bedroom house with pool table

Vacation Home in 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.
The price is AED 588
AED 1,543 total
includes taxes & fees
14 Dec - 15 Dec
Charming 3-bedroom house with pool table
Private kitchen
Honey Comb Hideout 3Br. House Albany

Vacation Home in Albany

The price is AED 735
AED 2,039 total
includes taxes & fees
11 Dec - 12 Dec
Honey Comb Hideout 3Br. House Albany
Game room
Pet Friendly Riverfront Home in Great Barrington

Vacation Home in Great Barrington

9.4 out of 10, Exceptional, (6)
The price is AED 744
AED 1,093 total
includes taxes & fees
15 Dec - 16 Dec
Pet Friendly Riverfront Home in Great Barrington
Property grounds
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Vacation Home in 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.
The price is AED 1,686
AED 3,134 total
includes taxes & fees
11 Dec - 12 Dec
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

Vacation Home in 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.
The price is AED 2,251
AED 4,038 total
includes taxes & fees
11 Dec - 12 Dec
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

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

10/10 Excellent
"This was a very cool new hotel. Easy walk into the cute town of Hudson. They are still working out some kinks, we didn’t have hot water but staff was very understanding and offered us "
Lisa 1-night trip
Posted 1 day ago
Pocketbook Hotel and Bath

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