Holiday Homes in Sheffield

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Sheffield holiday homes

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

1. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AU$588
includes taxes & fees
18 Nov - 19 Nov
Cheerful 3-bedroom cottage with woodstove
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

2. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is AU$463
includes taxes & fees
9 Nov - 10 Nov
Home in Great Barrington
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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!"
United States
Mary R.
The price is AU$955
includes taxes & fees
16 Nov - 17 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A modern interior with a loft-style ceiling, a grey sofa, a wooden coffee table, and a kitchen area with a large TV.

4. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is AU$879
includes taxes & fees
21 Nov - 22 Nov
Fantastic 2-bedroom house with AC in quaint Hillsdale.
A dining area with a wooden table, chairs, and a ceiling fan.

5. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great 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."
United States
Kelly B.
The price is AU$435
includes taxes & fees
9 Nov - 10 Nov
Leaf-Peeper Paradise in the Berkshires
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

6. 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, (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!"
United States
Roberta
The price is AU$1,807
includes taxes & fees
20 Nov - 21 Nov
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

7. 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."
United States
Eric H.
The price is AU$425
includes taxes & fees
9 Nov - 10 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.
A covered outdoor area with a brick floor, wooden furniture, and a fireplace.

8. Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington

Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington
Great Barrington
The price is AU$1,971
includes taxes & fees
10 Nov - 11 Nov
Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

9. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood 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!"
United States
William C B.
The price is AU$412
includes taxes & fees
12 Nov - 13 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A wooden cabin interior with a bench, a rug, and a hanging plant.

10. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (5 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is AU$276
includes taxes & fees
15 Nov - 16 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A rectangular swimming pool surrounded by a grassy area with a wooden fence and trees in the background.

11. Lockwood Manor: Autumn Escape on Six Private Acres with Heated Pool

Lockwood Manor: Autumn Escape on Six Private Acres with Heated Pool
Hillsdale
The price is AU$2,128
includes taxes & fees
15 Nov - 16 Nov
Lockwood Manor: Autumn Escape on Six Private Acres with Heated Pool
A hot tub with a string of lights above it, set against a dark night sky.

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AU$537
includes taxes & fees
15 Nov - 16 Nov
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

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 :)"
United States
Anonymous traveller
The price is AU$1,168
includes taxes & fees
1 Dec - 2 Dec
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

14. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is AU$894
includes taxes & fees
9 Nov - 10 Nov
Secluded Family Home in Serene Stockbridge Woods
A modern living room with a sectional sofa, wooden beams, a large window, and a view of the outdoors.

15. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires
West Stockbridge
The price is AU$1,820
includes taxes & fees
16 Nov - 17 Nov
Beautiful and Private Home Centrally Located in the Berkshires
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

16. 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."
United States
Brian C.
The price is AU$511
includes taxes & fees
9 Nov - 10 Nov
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A living room with a sofa, armchairs, a coffee table, and a television.

17. 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."
United States
Patricia O.
The price is AU$866
includes taxes & fees
9 Nov - 10 Nov
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A modern kitchen with white cabinets, a large island, and a skylight.

18. 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, (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!"
United States
Marianne R.
The price is AU$1,973
includes taxes & fees
9 Nov - 10 Nov
A Country Lodge Straight Out of the Pages of a Great Novel
A camping setup with a metal chair and a table by a river in a forest.

19. 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, (17 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is AU$472
includes taxes & fees
9 Nov - 10 Nov
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

20. NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is AU$1,034
includes taxes & fees
9 Nov - 10 Nov
NEW: Chic Modern Barn Style Home in Fun Area
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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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.

See all hotels in Sheffield
A lakeside town with autumn foliage, a bridge, and a rocky shoreline.