Holiday Homes in Sheffield

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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Featured Holiday 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 AU$704
includes taxes & fees
9 Nov - 10 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 AU$1,022
includes taxes & fees
4 Nov - 5 Nov
CT Gate House Goshen CT, Gate House Goshen CT
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
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 AU$613
includes taxes & fees
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
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 AU$612
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)
"Enjoyed our stay!!!"
United States
Fred W.
The price is AU$398
includes taxes & fees
28 Oct - 29 Oct
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 AU$718
includes taxes & fees
30 Oct - 31 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
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 AU$648
includes taxes & fees
19 Nov - 20 Nov
Bungalow in the Berkshires
Games room
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
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 AU$399
includes taxes & fees
29 Oct - 30 Oct
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
Fridge, microwave, oven, stovetop
Great Barrington Get Away
Great Barrington Get Away
9.4 out of 10, Exceptional, (23)
"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 AU$732
includes taxes & fees
31 Oct - 1 Nov
Great Barrington Get Away
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 AU$942
includes taxes & fees
4 Nov - 5 Nov
Cozy. Clean. Free bagel shop.
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 AU$1,810
includes taxes & fees
27 Oct - 28 Oct
Whispering Estate Guest House - A Romantic Countryside Getaway
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 AU$1,189
includes taxes & fees
28 Oct - 29 Oct
Spacious 5-bedroom house in charming Lee with WiFi
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 AU$695
includes taxes & fees
12 Nov - 13 Nov
rural, serene + sophisticated space
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)
"Wonderful property."
United States
Marie S.
The price is AU$1,436
includes taxes & fees
4 Nov - 5 Nov
The George is an elegant restored home in the Hudson Valley
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 AU$2,186
includes taxes & fees
22 Oct - 23 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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 AU$892
includes taxes & fees
2 Nov - 3 Nov
Tranquil Victorian on Charming Street
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Cozy. Clean. Free bagel shop. 3 Fireplaces.
The price is AU$912
includes taxes & fees
4 Nov - 5 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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
"Kitchen and parking both very good"
Joseph 1-night trip
Posted 2 days ago
Berkshire Mountain Lodge

Find out more about Sheffield

Sheffield Holiday Homes information

Number of reviews
116
Accommodation
451 Holiday Homes
Lowest Price
AU$398
Highest Price
AU$2,186