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Our top choices for Sheffield holiday homes
1. Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstoveSheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
Kelly R.
The price is NZ$724
includes taxes & fees
19 Nov - 20 Nov
2. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
Janet G.
The price is NZ$542
includes taxes & fees
13 Dec - 14 Dec
3. Cozy. Clean. Free bagel shop. 3 Fireplaces.
Cozy. Clean. Free bagel shop. 3 Fireplaces.Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
"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!"
Mary R.
The price is NZ$1,163
includes taxes & fees
20 Nov - 21 Nov
4. A Cozy Berkshire Escape l Close to the Slopes
A Cozy Berkshire Escape l Close to the SlopesGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
Kelly B.
The price is NZ$539
includes taxes & fees
16 Nov - 17 Nov
5. Fantastic 2-bedroom house with AC in quaint Hillsdale.
Fantastic 2-bedroom house with AC in quaint Hillsdale.Hillsdale
The price is NZ$1,077
includes taxes & fees
15 Nov - 16 Nov
6. Sweet Cozy Victorian in Housatonic. Close to everything.
Sweet Cozy Victorian in Housatonic. Close to everything.Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
Eric H.
The price is NZ$544
includes taxes & fees
15 Nov - 16 Nov
7. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness roomGreat Barrington
10.0 out of 10, Exceptional, (10 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!"
Roberta
The price is NZ$2,145
includes taxes & fees
20 Nov - 21 Nov
8. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
William C B.
The price is NZ$508
includes taxes & fees
18 Nov - 19 Nov
9. Peaceful and cozy 1 bed 1 bath in quaint Winchester
Peaceful and cozy 1 bed 1 bath in quaint WinchesterWinchester
10.0 out of 10, Exceptional, (6 reviews)
The price is NZ$331
includes taxes & fees
22 Nov - 23 Nov
10. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, CanoeingSherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
Frank M.
The price is NZ$661
includes taxes & fees
15 Nov - 16 Nov
11. Secluded Family Home in Serene Stockbridge Woods
Secluded Family Home in Serene Stockbridge WoodsStockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
Ofer C.
The price is NZ$1,076
includes taxes & fees
16 Nov - 17 Nov
12. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
Brian C.
The price is NZ$640
includes taxes & fees
15 Nov - 16 Nov
13. 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, (42 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
Anonymous traveller
The price is NZ$1,463
includes taxes & fees
7 Dec - 8 Dec
14. Beautiful and Private Home Centrally Located in the Berkshires
Beautiful and Private Home Centrally Located in the BerkshiresWest Stockbridge
The price is NZ$2,234
includes taxes & fees
30 Nov - 1 Dec
15. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.Chatham
10.0 out of 10, Exceptional, (18 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
Jess S.
The price is NZ$586
includes taxes & fees
15 Nov - 16 Nov
16. Sun Filled Lenox Retreat - Minutes to Tanglewood!
Sun Filled Lenox Retreat - Minutes to Tanglewood!Lee
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
Patricia O.
The price is NZ$1,077
includes taxes & fees
15 Nov - 16 Nov
17. A Country Lodge Straight Out of the Pages of a Great Novel
A Country Lodge Straight Out of the Pages of a Great NovelPine Plains
10.0 out of 10, Exceptional, (15 reviews)
"Stayed with a group for Millbrook Horse Trials, we had an amazing weekend at this calm and relaxing home with plenty of beds and amenities! What a treat!"
Marianne R.
The price is NZ$2,241
includes taxes & fees
16 Nov - 17 Nov
18. Lockwood Manor: Autumn Escape on Six Private Acres with Heated Pool
Lockwood Manor: Autumn Escape on Six Private Acres with Heated PoolHillsdale
The price is NZ$2,669
includes taxes & fees
15 Nov - 16 Nov
19. Charming Hudson Valley Escape | Autumn Vibes & Fire Pit
Charming Hudson Valley Escape | Autumn Vibes & Fire PitClaverack-Red Mills
10.0 out of 10, Exceptional, (1 review)
"amazing property - best rental i’ve ever stayed at. can’t recommend it enough"
jessica c.
20. The George is an elegant restored home in the Hudson Valley
The George is an elegant restored home in the Hudson ValleyStanfordville
9.8 out of 10, Exceptional, (15 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
Polly J.
The price is NZ$2,146
includes taxes & fees
22 Nov - 23 Nov
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.
Learn more about Sheffield
Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green.
