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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Vacation Homes in Sheffield

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
10 Dec - 11 Dec
Cheerful 3-bedroom cottage with woodstove
Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

Vacation Home in Goshen

2.5 star property
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is AED 390
AED 2,362 total
includes taxes & fees
10 Dec - 11 Dec
CT Gate House Goshen CT, Gate House Goshen CT
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 463
AED 825 total
includes taxes & fees
10 Dec - 11 Dec
Home in Great Barrington
Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 535
AED 1,386 total
includes taxes & fees
10 Dec - 11 Dec
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Exterior
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Vacation Home in Sherwood Forest

9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is AED 588
AED 1,441 total
includes taxes & fees
15 Dec - 16 Dec
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
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 1,984 total
includes taxes & fees
10 Dec - 11 Dec
Perfect House In Hillsdale, Brings Friends & Fam
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 890 total
includes taxes & fees
11 Dec - 12 Dec
Sweet Cozy Victorian in Housatonic. Close to everything.
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Vacation Home in Great Barrington

9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is AED 1,047
AED 1,904 total
includes taxes & fees
10 Dec - 11 Dec
Great Barrington Get Away
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
Exterior
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Vacation Home in Goshen

2.0 star property
The price is AED 912
AED 1,919 total
includes taxes & fees
10 Dec - 11 Dec
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
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
10 Dec - 11 Dec
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Fridge, microwave, oven, stovetop
Modern Ranch Retreat in Hudson Valley

Vacation Home in Millerton

10.0 out of 10, Exceptional, (4)
"Great communication and a fantastic property! The setting is quiet and short walk to downtown Millerton. The Harlem Valley Rail Trail Line is just down the road which offers excellent opportunities for adventures!"
United States
Scott E.
The price is AED 1,124
AED 2,019 total
includes taxes & fees
22 Dec - 23 Dec
Modern Ranch Retreat in Hudson Valley
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Vacation Home in Lee

8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is AED 1,561
AED 2,929 total
includes taxes & fees
15 Dec - 16 Dec
Spacious 5-bedroom house in charming Lee with WiFi
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Vacation Home in Great Barrington

10.0 out of 10, Exceptional, (2)
"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 AED 2,079
AED 4,878 total
includes taxes & fees
10 Dec - 11 Dec
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Interior
The George is an elegant restored home in the Hudson Valley

Vacation Home in Stanfordville

9.4 out of 10, Exceptional, (6)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
The price is AED 2,644
AED 4,130 total
includes taxes & fees
10 Dec - 11 Dec
The George is an elegant restored home in the Hudson Valley
Interior
rural, serene + sophisticated space

Vacation Home in Red Hook

10.0 out of 10, Exceptional, (7)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is AED 1,098
AED 1,407 total
includes taxes & fees
10 Dec - 11 Dec
rural, serene + sophisticated space
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Vacation Home in Great Barrington

The price is AED 1,249
AED 2,158 total
includes taxes & fees
21 Dec - 22 Dec
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Interior
Tranquil Victorian on Charming Street

Vacation Home in Hudson

6.0 out of 10, (1)
"Interior has been recently upgraded and is nicely done providing a pleasant stay. Host needs to be more responsive as we had an hours delay in accessing the property. Host did not respond to messages over a 6 hour period prior to arrival."
United States
Jim & Linda
The price is AED 915
AED 2,110 total
includes taxes & fees
19 Dec - 20 Dec
Tranquil Victorian on Charming Street
Fridge, microwave, oven, stovetop
Berkshire House Stay

Vacation Home in Lee

10.0 out of 10, Exceptional, (21)
"Wonderful stay, beautiful, well equipped and clean property. Highly recommend for an adult famiky getaway "
United States
jennifer r.
The price is AED 2,262
AED 4,057 total
includes taxes & fees
20 Dec - 21 Dec
Berkshire House Stay
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 Sheffield Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Great hospitality "
regina maria 1-night trip
Posted 20 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG