A covered wooden structure with a sloped roof, surrounded by greenery and trees.

Holiday Homes in Sheffield

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 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, (44 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AU$606
includes taxes & fees
12 Oct - 13 Oct
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, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is AU$467
includes taxes & fees
24 Sept - 25 Sept
Home in Great Barrington
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

3. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (26 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$439
includes taxes & fees
23 Sept - 24 Sept
Riverside Retreat in the Berkshires
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

4. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is AU$1,021
includes taxes & fees
23 Sept - 24 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

5. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is AU$811
includes taxes & fees
23 Sept - 24 Sept
Treetop Hideaway in Tyringham
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, (7 reviews)
"Beautiful house with great amenities in a convenient location. We loved the open concept that provided a great space for cooking, hanging out and playing games together while enjoying a beautiful view. The gameroom was so much fun, and we’d love to visit again when the sauna is finished. Our family of 6 and family dog loved it!"
United States
Rebecca K.
The price is AU$1,813
includes taxes & fees
23 Sept - 24 Sept
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very good, (1 review)
"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$402
includes taxes & fees
24 Sept - 25 Sept
Real Estate: Therapy - Lake, Laundry, Love it
A hot tub with a string of lights above it, set against a dark night sky.

8. 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, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AU$540
includes taxes & fees
27 Sept - 28 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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.

9. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$512
includes taxes & fees
29 Sept - 30 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

10. 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, (40 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$1,172
includes taxes & fees
2 Oct - 3 Oct
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

11. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
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$889
includes taxes & fees
23 Sept - 24 Sept
Chic Barn Style * Fireplace * Near Stissing House
A wooden cabin interior with a bench, a rug, and a hanging plant.

12. 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, (2 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is AU$314
includes taxes & fees
4 Oct - 5 Oct
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A camping setup with a metal chair and a table by a river in a forest.

13. 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, (15 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$466
includes taxes & fees
23 Sept - 24 Sept
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A two-story house with a balcony, a deck, and a view of the surrounding forest.

14. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (133 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is AU$1,021
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

15. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is AU$1,195
includes taxes & fees
18 Oct - 19 Oct
Stylish Mid-century Modern Berkshires Cape
A flat landscape with a clear sky and distant hills.

16. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is AU$1,005
includes taxes & fees
28 Sept - 29 Sept
Ellie’s Overlook, best view in the Berkshires!
A spacious room with a wooden ceiling, large windows, and a chandelier.

17. Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is AU$1,034
includes taxes & fees
28 Sept - 29 Sept
Luxury Barn Retreat — All-Season Escape Awaits!
A covered outdoor deck with a grill, a chair, and a view of a lake and forest.

18. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is AU$974
includes taxes & fees
23 Sept - 24 Sept
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A modern kitchen with white cabinets, a large island, and a skylight.

19. 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)
"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 AU$1,854
includes taxes & fees
16 Oct - 17 Oct
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"We go to Western Massachusetts twice a year - some years it's more. Since discovering Berkshire Mountain Lodge, we have not been able to stay anywhere else. The staff have always been so pleasant and the room always smelled clean when you walk through the door."
Jonathan 2-night trip
Posted less than an hour ago
Berkshire Mountain Lodge

Find out more about Sheffield

Sheffield Holiday Homes information

Number of reviews
6,991
Accommodation
416 Holiday Homes
Lowest Price
AU$109
Highest Price
AU$562