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Vacation Homes in Sheffield

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 SAR 889
SAR 1,857 total
includes taxes & fees
9 Sep - 10 Sep
Cheerful 3-bedroom cottage with woodstove

The Race Mountain House

2.0 star property
9.2 out of 10, Wonderful, (5)
"I spent my 60th birthday with a few friends at Mountain House and it was even better than I dreamed. The comfort and simplicity of the decor along with the mountain views. A must for those who like simple elegance."
The Race Mountain House

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 SAR 608
SAR 1,488 total
includes taxes & fees
24 Sep - 25 Sep
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
10.0 out of 10, Exceptional, (5)
"Wonderful stay. It really is a gate house. The property is beautiful and the house is spacious. If I was eloquent,I could go on and on... "
The price is SAR 664
SAR 2,726 total
includes taxes & fees
9 Oct - 10 Oct
CT Gate House Goshen CT, Gate House Goshen CT

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."
The price is SAR 668
SAR 1,559 total
includes taxes & fees
22 Sep - 23 Sep
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Enjoyed our stay!!!"
The price is SAR 604
SAR 1,011 total
includes taxes & fees
10 Sep - 11 Sep
Home in Great Barrington

Sun Filled Lenox Retreat - Minutes to Tanglewood!

10.0 out of 10, Exceptional, (2)
"Clean, nicely decorated, very well equipped home . We were 3 couples having a family reunion and attending a concert at Tanglewood. Comfortable beds. The wagon was very useful for our trip to Tanglewood. Would return again. Suggestions are to provide an umbrella for the deck- it was hot. Would have liked lawn chairs ( there was only 1) . Needs new decking. "
The price is SAR 856
SAR 1,928 total
includes taxes & fees
9 Sep - 10 Sep
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Whispering Estate Guest House - A Romantic Countryside Getaway

10.0 out of 10, Exceptional, (2)
"Beautiful property and great location. A true retreat. "
The price is SAR 1,501
SAR 2,651 total
includes taxes & fees
9 Sep - 10 Sep
Whispering Estate Guest House - A Romantic Countryside Getaway

Cozy 2BR/1BA Furnished In-Apartment – Quiet Country

The price is SAR 396
SAR 1,204 total
includes taxes & fees
9 Sep - 10 Sep
Cozy 2BR/1BA Furnished In-Apartment – Quiet Country

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (2)
"Great location, very clean and well appointed with everyth"
The price is SAR 1,407
SAR 1,911 total
includes taxes & fees
9 Sep - 10 Sep
Bungalow in the Berkshires

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Spacious 5-bedroom house in charming Lee with WiFi

The price is SAR 1,098
SAR 2,307 total
includes taxes & fees
15 Sep - 16 Sep
Spacious 5-bedroom house in charming Lee with WiFi

Cozy Carriage House room with a double bed and private balcony

The price is SAR 898
SAR 1,293 total
includes taxes & fees
14 Sep - 15 Sep
Cozy Carriage House room with a double bed and private balcony

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. "
The price is SAR 1,126
SAR 1,995 total
includes taxes & fees
1 Oct - 2 Oct
Great Barrington Get Away

Cozy. Clean. Free bagel shop. 3 Fireplaces.

The price is SAR 1,351
SAR 2,263 total
includes taxes & fees
11 Sep - 12 Sep
Cozy. Clean. Free bagel shop. 3 Fireplaces.

The George is an elegant restored home in the Hudson Valley

9.2 out of 10, Wonderful, (5)
"Wonderful property."
The price is SAR 2,161
SAR 3,485 total
includes taxes & fees
9 Sep - 10 Sep
The George is an elegant restored home in the Hudson Valley

rural, serene + sophisticated space

10.0 out of 10, Exceptional, (7)
"Beautiful property with unique accommodations in the Hudson Valley"
The price is SAR 1,122
SAR 1,647 total
includes taxes & fees
14 Sep - 15 Sep
rural, serene + sophisticated space

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

The price is SAR 838
SAR 1,217 total
includes taxes & fees
10 Sep - 11 Sep
Elegant Carriage House room with a queen bed and private patio.

Experience Timeless Elegance in The Edith Wharton Room!

The price is SAR 778
SAR 1,142 total
includes taxes & fees
9 Sep - 10 Sep
Experience Timeless Elegance in The Edith Wharton Room!

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

The price is SAR 1,349
SAR 1,858 total
includes taxes & fees
10 Sep - 11 Sep
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
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