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Compare 368 Vacation Homes in Sheffield with updated reviews, rates, and availability.

Spectacular views and close to Great Barrington.
Private kitchen

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Breakfast Nook - wake up to the best sunshine ever!

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.
Christmas at Lakeview Retreat

Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

10.0 out of 10, Exceptional, (20)
"clean, wonderful views of the lake. "
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.
Berkshire Ski House on Lake Garfield w/HT By Great Barrington
Our house location

Berkshire Ski House on Lake Garfield w/HT By Great Barrington

10.0 out of 10, Exceptional, (3)
"We had a lovely stay! The space was perfect for our group of 4 moms looking for a peaceful getaway. The host was very responsive. Only note for those visiting, rideshares (Uber and otherwise) are few and far between. Schedule ahead! We'd definitely stay again :)"
Berkshire Ski House on Lake Garfield w/HT By Great Barrington
Beautiful Berkshire Farm House on 160+ Acres
Exterior

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (34)
"The house was spacious and comfortable for our large group (13 people). The basketball court in the barn was a lot of fun."
Beautiful Berkshire Farm House on 160+ Acres
Quintessential 6-BR Berkshires Lodge

Quintessential 6-BR Berkshires Lodge

9.8 out of 10, Exceptional, (8)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Great Room with lake view

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

10.0 out of 10, Exceptional, (90)
"Very clean, spacious, and comfortable. Property manager’s information was helpful."
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Exterior

Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

10.0 out of 10, Exceptional, (112)
"A very nice place in a very nice part of the state. Perfect for groups and families. "
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Hudson Valley and The Berkshires getaway
Kitchen and dining room

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (3)
"We very much enjoyed our stay at this lovely home. The hosts were wonderful communicators!"
Hudson Valley and The Berkshires getaway
Serene Salisbury Rental Home on 26 Acres w/ Deck!
Salisbury Vacation Rental | 6BR | 3.5BA | 2,525 Sq Ft | 2 Steps to Enter

Serene Salisbury Rental Home on 26 Acres w/ Deck!

9.8 out of 10, Exceptional, (7)
"Great weekend getaway with family to celebrate "
Serene Salisbury Rental Home on 26 Acres w/ Deck!
Woodland Zen by AvantStay | Modern Design + Patio
Welcome to Woodland Zen!

Woodland Zen by AvantStay | Modern Design + Patio

10.0 out of 10, Exceptional, (5)
"This home is large, full of light and has modern decor. Mostly bare floors so bring slippers/socks for cold nights. Fully appointed kitchen that has everything, including plenty of trash bags, dish soap, pots, pans, dishes, etc. We cooked several meals there and it was easy to do. Bedroom windows have blinds, bathroom windows do not! The house is surrounded by trees but showering in a room with bare windows took some getting used to. There are many light switches that some labeling might be...
Woodland Zen by AvantStay | Modern Design + Patio
Beautiful home on acres with deck, fenced area & fireplace

Beautiful home on acres with deck, fenced area & fireplace

10.0 out of 10, Exceptional, (2)
Beautiful home on acres with deck, fenced area & fireplace
Pristine Home In Becket Woods

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Living area

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (18)
"Very nice, as expected! "
The price is AED 694
AED 1,353 total
includes taxes & fees
30 Nov - 1 Dec
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Great Barrington Walkable to Lake and Town!

Great Barrington Walkable to Lake and Town!

9.6 out of 10, Exceptional, (5)
"Needed a rental in a hurry, lucked into Lucas’ house. Quiet, comfortable and cozy. Great visit. Thank you for hosting me and Birdie. "
Great Barrington Walkable to Lake and Town!
Enjoy comfortable elegance in this secluded grand home located in town
Property grounds

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (65)
"Beautiful home perfect for our multi-generational family. We loved the separate spaces and easy walk to the town center. We can’t wait to come back!"
Enjoy comfortable elegance in this secluded grand home located in town
Private Access To Laurel Lake, Enjoy Lake Life

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life
Modern Glass House designed by renowned architect Thomas Phifer
Property grounds

Modern Glass House designed by renowned architect Thomas Phifer

8.8 out of 10, Excellent, (3)
"For those of us who live in big Cities. This is truly a rare find! It’s so different and so unique! We were thrilled with the view and massive outdoor space. We love it so much! We will keep this house when we are in the area in the future! "
Modern Glass House designed by renowned architect Thomas Phifer
Elegant 19th Century New England 2BR vacation rental at Garfield House
Exterior

Elegant 19th Century New England 2BR vacation rental at Garfield House

10.0 out of 10, Exceptional, (88)
"Pretty darn perfect but not quite as clean as last year. Maybe different crew?"
Elegant 19th Century New England 2BR vacation rental at Garfield House
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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Other property types in Sheffield

Cheerful 3-bedroom cottage with woodstove
great kitchen for cooking in

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (30)
"Delightful home in very quiet neighborhood near hiking trails. House had every amenity you might need (except tissues). Less than 20 minutes drive from Sheffield. Great restaurants in town. We very much enjoyed our stay in this house in the country and would highly recommend it to anyone wanting to stay in the area."
The price is AED 871
AED 1,863 total
includes taxes & fees
4 Dec - 5 Dec
Cheerful 3-bedroom cottage with woodstove
Antique Farmhouse Totally Restored
Sunrise lights up the front of the house. Moon sets over the mountain.

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake
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.