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31 Oct - 2 Nov
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7 Nov - 9 Nov
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21 Nov - 23 Nov
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19 Dec - 21 Dec

Vacation Homes in Sheffield

Property grounds
Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 724
AED 1,658 total
includes taxes & fees
11 Nov - 12 Nov
Cheerful 3-bedroom cottage with woodstove
Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT
CT Gate House Goshen CT, Gate House Goshen CT
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 433
AED 2,419 total
includes taxes & fees
2 Nov - 3 Nov
CT Gate House Goshen CT, Gate House Goshen CT
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 536
AED 1,386 total
includes taxes & fees
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
9.6 out of 10, Exceptional, (8)
"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
27 Oct - 28 Oct
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Fridge, microwave, oven, stovetop
Home in Great Barrington
Home in Great Barrington
9.8 out of 10, Exceptional, (24)
"Crisp and clean with a great location.Wonderful choice."
United States
Richard B.
The price is AED 698
AED 1,120 total
includes taxes & fees
23 Nov - 24 Nov
Home in Great Barrington
Fridge, microwave, oven, stovetop
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is AED 698
AED 1,719 total
includes taxes & fees
30 Oct - 31 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop
Great Barrington Get Away
Great Barrington Get Away
9.4 out of 10, Exceptional, (24)
"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "
United States
Amy B.
The price is AED 937
AED 1,764 total
includes taxes & fees
27 Oct - 28 Oct
Great Barrington Get Away
Exterior
Bungalow in the Berkshires
Bungalow in the Berkshires
10.0 out of 10, Exceptional, (3)
"We had a lovely stay. Easy check in and communication was great. "
United States
Dale G.
The price is AED 1,102
AED 1,534 total
includes taxes & fees
26 Oct - 27 Oct
Bungalow in the Berkshires
Game room
Pet Friendly Riverfront Home in Great Barrington
Pet Friendly Riverfront Home in Great Barrington
9.0 out of 10, Wonderful, (2)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AED 744
AED 950 total
includes taxes & fees
29 Oct - 30 Oct
Pet Friendly Riverfront Home in Great Barrington
Smart TV, fireplace, books
Cozy. Clean. Free bagel shop.
Cozy. Clean. Free bagel shop.
10.0 out of 10, Exceptional, (10)
"The perfect location for a stay in Great Barrington. The house is so well done and very comfortable!"
United States
Carly F.
The price is AED 1,322
AED 2,232 total
includes taxes & fees
4 Nov - 5 Nov
Cozy. Clean. Free bagel shop.
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi
Spacious 5-bedroom house in charming Lee with WiFi
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is AED 1,322
AED 2,626 total
includes taxes & fees
30 Oct - 31 Oct
Spacious 5-bedroom house in charming Lee with WiFi
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (1)
"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 2,311
AED 5,174 total
includes taxes & fees
25 Oct - 26 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Exterior detail
Whispering Estate Guest House - A Romantic Countryside Getaway
Whispering Estate Guest House - A Romantic Countryside Getaway
10.0 out of 10, Exceptional, (4)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is AED 2,938
AED 4,457 total
includes taxes & fees
26 Oct - 27 Oct
Whispering Estate Guest House - A Romantic Countryside Getaway
Interior
The George is an elegant restored home in the Hudson Valley
The George is an elegant restored home in the Hudson Valley
9.2 out of 10, Wonderful, (5)
"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 2,116
AED 3,445 total
includes taxes & fees
27 Oct - 28 Oct
The George is an elegant restored home in the Hudson Valley
Interior
rural, serene + sophisticated space
rural, serene + sophisticated space
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 1,641 total
includes taxes & fees
10 Nov - 11 Nov
rural, serene + sophisticated space
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Cozy. Clean. Free bagel shop. 3 Fireplaces.
The price is AED 1,249
AED 2,158 total
includes taxes & fees
4 Nov - 5 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Interior
Tranquil Victorian on Charming Street
Tranquil Victorian on Charming Street
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
26 Oct - 27 Oct
Tranquil Victorian on Charming Street
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"We loved this place. Quiet, very clean,attractive. Loved that it had a kitchen area. Second story, sliding glass doors overlooked the fall foliage in the back of the building. Very peaceful.."
Steven 4-night trip
Posted 2 days ago
Berkshire Mountain Lodge