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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Browse Select Sheffield Holiday Homes

Cheerful 3-bedroom cottage with woodstove
Property grounds

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."
The price is £371
includes taxes & fees
14 Sept - 15 Sept
Cheerful 3-bedroom cottage with woodstove
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Outdoor dining

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."
The price is £301
includes taxes & fees
1 Sept - 2 Sept
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
CT Gate House Goshen CT, Gate House Goshen CT
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
10.0 out of 10, Exceptional, (2)
"The property was great and the house was huge even for all 12 of us "
The price is £546
includes taxes & fees
24 Aug - 25 Aug
CT Gate House Goshen CT, Gate House Goshen CT
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Smart TV, books

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

9.8 out of 10, Exceptional, (7)
"My wife, two kids, and chocolate lab spent a few days at the cottage to enjoy the snow and hot tub. Everything was set up exactly as described and Nicole was very friendly and proactive. We had a great time and would do it again "
The price is £313
includes taxes & fees
2 Sept - 3 Sept
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Home in Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Our family had a wonderful experience and stay. "
The price is £241
includes taxes & fees
19 Aug - 20 Aug
Home in Great Barrington
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop

Sun Filled Lenox Retreat - Minutes to Tanglewood!

10.0 out of 10, Exceptional, (1)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
The price is £382
includes taxes & fees
15 Sept - 16 Sept
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Charming Retreat at Stone Hill Estate – Nature Meets Luxury
Dining

Charming Retreat at Stone Hill Estate – Nature Meets Luxury

The price is £682
includes taxes & fees
17 Aug - 18 Aug
Charming Retreat at Stone Hill Estate – Nature Meets Luxury
Bungalow in the Berkshires
Exterior

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (1)
"Renting this house was very last minute because the place we initially booked fell through - and we're so glad it did! The house was charming, cozy, up-to-date, and beautifully decorated. The neighborhood was nice and quiet, and the drive to downtown was short. I highly recommend this house!"
The price is £390
includes taxes & fees
27 Aug - 28 Aug
Bungalow in the Berkshires
Perfect House In Hillsdale, Brings Friends & Fam
Exterior

Perfect House In Hillsdale, Brings Friends & Fam

8.6 out of 10, Excellent, (4)
"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. "
The price is £395
includes taxes & fees
25 Aug - 26 Aug
Perfect House In Hillsdale, Brings Friends & Fam
Great Barrington Get Away
Fridge, microwave, oven, stovetop

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is £429
includes taxes & fees
1 Sept - 2 Sept
Great Barrington Get Away
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

The price is £226
includes taxes & fees
1 Sept - 2 Sept
Experience Timeless Elegance in The Edith Wharton Room!
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is £602
includes taxes & fees
23 Aug - 24 Aug
Spacious 5-bedroom house in charming Lee with WiFi
The George is an elegant restored home in the Hudson Valley
Interior

The George is an elegant restored home in the Hudson Valley

9.2 out of 10, Wonderful, (5)
"Nice big house in a quiet location. "
The price is £700
includes taxes & fees
19 Aug - 20 Aug
The George is an elegant restored home in the Hudson Valley
rural, serene + sophisticated space
Interior

rural, serene + sophisticated space

10.0 out of 10, Exceptional, (7)
"Beautiful property with unique accommodations in the Hudson Valley"
The price is £330
includes taxes & fees
16 Sept - 17 Sept
rural, serene + sophisticated space
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, WiFi, bed sheets

Elegant Carriage House room with a queen bed and private patio.

The price is £241
includes taxes & fees
3 Sept - 4 Sept
Elegant Carriage House room with a queen bed and private patio.
Cozy Carriage House room with a double bed and private balcony
1 bedroom, bed sheets

Cozy Carriage House room with a double bed and private balcony

The price is £256
includes taxes & fees
1 Sept - 2 Sept
Cozy Carriage House room with a double bed and private balcony
Historic Susan B. Anthony Room - Cozy & Charming Stay
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is £271
includes taxes & fees
1 Sept - 2 Sept
Historic Susan B. Anthony Room - Cozy & Charming Stay
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Fireplace

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

The price is £344
includes taxes & fees
1 Sept - 2 Sept
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
1 bedroom, bed sheets

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

The price is £368
includes taxes & fees
14 Sept - 15 Sept
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Fireplace

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

The price is £414
includes taxes & fees
15 Sept - 16 Sept
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
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

Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"A great mom & pop motel. Clean and friendly "
Glenn 1-night trip
Posted 2 days ago
Monument Mountain Motel