Holiday Homes in Sheffield

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Featured Holiday Homes in Sheffield

Amore Estate - beautiful room with many places to explore and relax in.
9.6 out of 10, Exceptional, (15)
"Our mix of family and friends had a wonderful time at your home over the Labor Day weekend. The space was clean, spacious and beautiful. The property had plenty for everyone to do. We will definitely be booking again. "
Amore Estate - beautiful room with many places to explore and relax in.
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
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (26)
"Impeccably clean, wonderful owner, kitchen with everything, strong WiFi, luxurious master bath. "
The price is NZ$798
includes taxes & fees
13 Oct - 14 Oct
Cheerful 3-bedroom cottage with woodstove
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.
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (20)
"The house is lovely and so perfectly located. The two bedrooms were sufficiently apart and next to their own bathrooms so both couples had privacy.the screened in porch was perfect to hang out and play cards at night and my dog absolutely loved the back yard. The location is superb, conviently located central to Stockbridge, ,lenox and Great Barrington. Fifteen minutes to Tanglewood and the Norman Rockwell museums. There are so many hiking trails with fabulous mountain views nearby."
Stockbridge Home, Come Experience The Berkshires!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.6 out of 10, Exceptional, (13)
"Me and my husband and my sister and her husband came to the Hudson Valley to place a bench in his hometown in his memory. We thoroughly enjoyed our time at this property. It was just exactly what we needed-quiet and relaxing!"
The price is NZ$525
includes taxes & fees
29 Sept - 30 Sept
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Relax or be active! The choice is yours in this pet-friendly family home.
10.0 out of 10, Exceptional, (5)
"The house was so New England! Huge yard private setting. House was fully stocked and the kitchen had great appliances with anything you would need . Deck off the kitchen was so nice . Plenty of space to spread out . I would definitely recommend this home to anyone ! Thanks Terri Marino"
Relax or be active! The choice is yours in this pet-friendly family home.
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, (141)
"Great place and views. "
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
9.4 out of 10, Exceptional, (34)
"My grown daughter and I stayed here for a two night visit to the Berkshires. It was so nice to have an entire house rather than a hotel room! We received our check in email in plenty of time, the house was clean and furnished with generous amenities such as soaps, shampoos, coffee, etc., the owner was readily available. The house is close to the road, but it really wasn’t a problem…white noise machines and air purifiers made sleeping very comfortable, and there was very little traffic noise....
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
The Goshen Glass Chalet
9.4 out of 10, Exceptional, (24)
"Everything was clean, and was a very comfortable home for friends and family."
The Goshen Glass Chalet
Enjoy comfortable elegance in this secluded grand home located in town
10.0 out of 10, Exceptional, (64)
"Perfectly located and lovely appointments make this the place to stay when visiting Lenox, Tanglewood, etc. The home is farm in style but elegantly decorated with thoughtful combinations of old and new. Well laid out floor plan allows groups to host friends and families at the same time. You will be delighted by mornings in the kitchen or evenings in the living spaces. Enjoy! "
Enjoy comfortable elegance in this secluded grand home located in town
Private Access To Laurel Lake, Enjoy Lake Life
9.8 out of 10, Exceptional, (10)
"Enjoy easy access to Laurel Lake, Lenox and High Lawn Farm from this lovely space! A quick walk to the dock across the street affords time by the water to read, swim or kayak. The kitchen is nicely appointed, the house heats and cools very efficiently and the owners are wonderfully communicative. Had a great stay and would return!"
Private Access To Laurel Lake, Enjoy Lake Life
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10.0 out of 10, Exceptional, (17)
"At the end of a dead-end street but only two blocks from the center of Stockbridge, this century-old charmer may be the best-kept and best-supplied rental in the Berkshires. We stayed a month(!) and loved it. The location is unbeatable, an easy walk from the Red Lion and within 15 minutes of Tanglewood, The Mount, the Rockwell museum and other attractions. Four local trails begin 100 feet away, including the Ice Glen. A beautiful, productive garden awaits, and the screened front porch may be...
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Cozy Retreat on Copake Lake in our Charming Home
9.6 out of 10, Exceptional, (38)
"We had a lovely weekend at Alex's home. We had everything we needed as the house was well stocked. Alex was very quick to respond to all our inquiries! We loved the central location and the fireplace was perfect for the cool nights! We hiked, shopped and enjoyed the board games at night! Would recommend! "
Cozy Retreat on Copake Lake in our Charming Home
Whitney by AvantStay | Private Berkshires Estate
8.0 out of 10, Very good, (7)
"We spent a lovely 2 weeks here. We had some septic issues that were remedied quickly. Overall, the house was comfortable and provided easy access to all the Berkshires have to offer."
Whitney by AvantStay | Private Berkshires Estate
Your Invited to the Berkshires!
9.8 out of 10, Exceptional, (29)
"Clean, updated home in the perfect location. Loved the screens in porch! Holly is a wonderful host and her home is a perfect getaway."
Your Invited to the Berkshires!
Mountain View Getaway
10.0 out of 10, Exceptional, (41)
"This is our second year staying with at Karen and Larry’s property and it did not disappoint. They are incredible hosts and their home is conveniently located near the Lime Rock Track (less than 3 miles). It’s a beautiful and peaceful setting and extremely comfortable home. We highly recommend."
Mountain View Getaway
Private, lake community house in the serene Berkshire Foothills with pool table
10.0 out of 10, Exceptional, (3)
Private, lake community house in the serene Berkshire Foothills with pool table
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (9)
"Near Jacob's Pillow!"
Pristine Home In Becket Woods
Peace and quiet on the lake
9.6 out of 10, Exceptional, (190)
"Loved it!"
Peace and quiet on the lake
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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
10.0 out of 10, Exceptional, (26)
"Impeccably clean, wonderful owner, kitchen with everything, strong WiFi, luxurious master bath. "
The price is NZ$798
includes taxes & fees
13 Oct - 14 Oct
Cheerful 3-bedroom cottage with woodstove
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (82)
"We had 15 people stay for three nights for a family reunion - 9 adults and 6 kids. The house worked well, as all had reasonably private spaces. The countryside is beautiful. Visits to a lake for swimming and several local waterfalls worked well for all."
Antique Farmhouse Totally Restored
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (205)
"My stay was shorter than I had planned but the few days I was here was so relaxing. First of all, the bed is so comfortable, I slept like a baby. Very quiet area. Nice to walk around with my dogs and explore. The cottage was nicely outfitted with any needs you might have. Beautiful time of year to stay here! I cannot wait to go back. I also want to say I appreciate that they allowed my two dogs. My dogs are very well behaved, and I travel with them quite often. Not all places allow this, so I...
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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.