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Our top choices for Sheffield vacation homes

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ¥37,408
¥79,692 total
includes taxes & fees
Mar 30 - Mar 31
Cheerful 3-bedroom cottage with woodstove

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is ¥25,286
¥62,271 total
includes taxes & fees
Mar 30 - Mar 31
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
Goshen
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is ¥16,763
¥101,986 total
includes taxes & fees
Mar 23 - Mar 24
CT Gate House Goshen CT, Gate House Goshen CT

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is ¥29,264
¥47,498 total
includes taxes & fees
Mar 25 - Mar 26
Home in Great Barrington

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ¥23,013
¥57,970 total
includes taxes & fees
Apr 1 - Apr 2
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ¥31,963
¥49,984 total
includes taxes & fees
Mar 22 - Mar 23
Cozy Riverside Berkshires Retreat

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is ¥41,670
¥88,424 total
includes taxes & fees
Mar 31 - Apr 1
Treetop Hideaway in Tyringham

Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (2 reviews)
"Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! "
United States
Timothy S.
The price is ¥52,876
¥98,997 total
includes taxes & fees
Mar 24 - Mar 25
Luxury Barn Retreat — All-Season Escape Awaits!

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Goshen
10.0 out of 10, Exceptional, (1 review)
"Without a doubt, we will be back! Your home was so beautiful, warm and comfortable. Our host was so helpful and friendly. We can't thank you enough for providing such a wonderful experience to our trip. "
United States
Linda D.
The price is ¥41,828
¥92,455 total
includes taxes & fees
Mar 30 - Mar 31
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 reviews)
"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."
United States
Paulo I.
The price is ¥28,411
¥72,638 total
includes taxes & fees
Mar 29 - Mar 30
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (35 reviews)
"Julie was an excellent host. She responded quickly to my questions and provided us with a long list of local restaurants and activities.The house is lovely! It was very clean and had everything that we would need for our stay. We appreciated the big kitchen and the open living room- dining room space. "
United States
Kathleen E.
The price is ¥56,665
¥114,600 total
includes taxes & fees
Mar 26 - Mar 27
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is ¥59,190
¥115,834 total
includes taxes & fees
Apr 1 - Apr 2
Spacious 5-bedroom house in charming Lee with WiFi

rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is ¥47,194
¥67,530 total
includes taxes & fees
Mar 24 - Mar 25
rural, serene + sophisticated space

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

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"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 ¥90,889
¥212,898 total
includes taxes & fees
Mar 22 - Mar 23
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
8.0 out of 10, Very Good, (1 review)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is ¥27,622
¥48,261 total
includes taxes & fees
Mar 31 - Apr 1
Renovated house. Built in 1890s. No neighbors in sight.

The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.4 out of 10, Exceptional, (6 reviews)
"This our 3rd stay at the property and once again we thoroughly enjoyed the house and the grounds. We had an opportunity to enjoy horseback riding on site and would definitely recommend that to any visitors. The hosts were very kind and hospitable. "
United States
Eric L.
The price is ¥113,645
¥174,273 total
includes taxes & fees
Mar 31 - Apr 1
The George is an elegant restored home in the Hudson Valley

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is ¥63,916
¥106,021 total
includes taxes & fees
Apr 14 - Apr 15
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Whispering Estate Guest House - Countryside Getaway

Whispering Estate Guest House - Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is ¥85,234
¥136,137 total
includes taxes & fees
Mar 21 - Mar 22
Whispering Estate Guest House - Countryside Getaway

Secluded escape w/ hot tub + pizza oven+ fireplace

Secluded escape w/ hot tub + pizza oven+ fireplace
Taghkanic
The price is ¥67,556
¥173,246 total
includes taxes & fees
Apr 20 - Apr 21
Secluded escape w/ hot tub + pizza oven+ fireplace

A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (13 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is ¥140,478
¥229,983 total
includes taxes & fees
Apr 3 - Apr 4
A Country Lodge Straight Out of the Pages of a Great Novel
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

Find out more about Sheffield

Sheffield Vacation Homes information

Number of reviews
203
Accommodation
437 Vacation Homes
Lowest Price
¥47,498
Highest Price
¥229,983