A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

Holiday Homes in Sheffield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is €374
includes taxes & fees
9 Nov - 10 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, (39 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is €323
includes taxes & fees
26 Oct - 27 Oct
Home in Great Barrington
A staircase with a wooden handrail and a white wall with a light switch.

3. 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 €247
includes taxes & fees
26 Oct - 27 Oct
Leaf-Peeper Paradise 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 €639
includes taxes & fees
19 Oct - 20 Oct
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A dining area with a wooden table, black chairs, and a vase with green plants.

5. 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)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is €310
includes taxes & fees
18 Oct - 19 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
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, (9 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 €1,182
includes taxes & fees
22 Oct - 23 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

7. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 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 €509
includes taxes & fees
9 Nov - 10 Nov
Treetop Hideaway in Tyringham
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

8. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (29 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is €589
includes taxes & fees
20 Oct - 21 Oct
Secluded Family Home in Serene Stockbridge Woods
A wooden cabin interior with a bench, a rug, and a hanging plant.

9. 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, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is €196
includes taxes & fees
1 Nov - 2 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 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 €279
includes taxes & fees
3 Nov - 4 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A two-story house with a balcony, a deck, and a view of the surrounding forest.

11. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (134 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 €538
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
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.

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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is €342
includes taxes & fees
27 Oct - 28 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

13. 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.
Stylish Mid-century Modern Berkshires Cape
A hot tub with a string of lights above it, set against a dark night sky.

14. 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, (18 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is €356
includes taxes & fees
28 Oct - 29 Oct
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A modern living room with a sofa, armchair, coffee table, and TV.

15. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.6 out of 10, Exceptional, (4 reviews)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is €528
includes taxes & fees
19 Oct - 20 Oct
Spacious Central Berkshires Home for Groups
A living room with a sofa, armchairs, a coffee table, and a television.

16. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (11 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 €554
includes taxes & fees
16 Oct - 17 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A camping setup with a metal chair and a table by a river in a forest.

17. 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, (16 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 €304
includes taxes & fees
19 Oct - 20 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

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

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is €621
includes taxes & fees
25 Oct - 26 Oct
Ellie’s Overlook, best view in the Berkshires!
A cozy living room with a sofa, a fireplace, and large windows.

19. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is €624
includes taxes & fees
21 Oct - 22 Oct
Luxury Barn Near Hudson With New Private Sauna
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

20. 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 €932
includes taxes & fees
21 Oct - 22 Oct
Chic Barn Style * Fireplace * Near Stissing 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sheffield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Wonderful"
Philippe 2-night trip
Posted 1 hour ago
The Red Lion Inn

Find out more about Sheffield

Sheffield Holiday Homes information

Number of reviews
365
Accommodation
409 Holiday Homes
Lowest Price
€196
Highest Price
€1,182