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

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

Recommended hotels in Sheffield

Interior detail

1. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."
United States
Liliana
The price is CA $229
CA $256 total
includes taxes & fees
Nov 10 - Nov 11
Wilder House Berkshires
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

2. 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 CA $248
CA $572 total
includes taxes & fees
Nov 19 - Nov 20
Cheerful 3-bedroom cottage with woodstove
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

3. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,000 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
United States
Lynne
The price is CA $106
CA $118 total
includes taxes & fees
Nov 29 - Nov 30
Quality Inn Great Barrington
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

4. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (939 reviews)
"Super clean and cozy and safe"
United States
Andrea
The price is CA $84
CA $93 total
includes taxes & fees
Nov 8 - Nov 9
Monument Mountain Motel
An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

5. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (854 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
The price is CA $116
CA $130 total
includes taxes & fees
Dec 3 - Dec 4
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

6. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (626 reviews)
"Stay was great. Staff very friendly and helpful. 1 guest was screaming at someone at 4am but other than that it was a great stay"
United States
Sherry
The price is CA $110
CA $123 total
includes taxes & fees
Nov 6 - Nov 7
Travelodge by Wyndham Great Barrington Berkshires
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

7. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (820 reviews)
"Nice view and location for fall color."
United States
Md
The price is CA $224
CA $251 total
includes taxes & fees
Nov 10 - Nov 11
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

8. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (58 reviews)
"East Rock was a nice, clean, and comfortable place to stay. Everything was great, and I enjoyed my stay."
United States
Sharon
The price is CA $172
CA $192 total
includes taxes & fees
Dec 6 - Dec 7
East Rock Inn
A large house with a balcony and a grassy yard.

9. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (637 reviews)
"A fine place for a quick overnight trip to the Berkshires."
United States
David
The price is CA $116
CA $129 total
includes taxes & fees
Nov 9 - Nov 10
The Little Lion
A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

10. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (454 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
The price is CA $147
CA $169 total
includes taxes & fees
Nov 6 - Nov 7
Locust Tree Bed and Breakfast LLC
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

11. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (155 reviews)
"Beyond amazing, we loved it so much!"
United States
Stacy
The price is CA $200
CA $224 total
includes taxes & fees
Dec 6 - Dec 7
Little Cat Lodge
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

12. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is CA $107
CA $149 total
includes taxes & fees
Nov 12 - Nov 13
Cozy 1-bedroom studio in serene Great Barrington with AC
A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

13. the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (291 reviews)
"Super cute, fairly clean and such a lovely breakfast!"
United States
Luis
The price is CA $231
CA $258 total
includes taxes & fees
Nov 20 - Nov 21
the Alander
A wooden cabin with a deck, large windows, and outdoor seating.

14. The Cozy Cat Motel

The Cozy Cat Motel
Copake Falls
The price is CA $208
CA $233 total
includes taxes & fees
Nov 8 - Nov 9
The Cozy Cat Motel
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

15. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (251 reviews)
"Great Breakfast Bed was okay Room very quaint hotel was very nice inside"
United States
Melanie
The price is CA $247
CA $284 total
includes taxes & fees
Nov 11 - Nov 12
Blackberry River Inn
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

16. Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
10.0 out of 10, Exceptional, (51 reviews)
"Great experience!"
United States
Sunny
The price is CA $334
CA $420 total
includes taxes & fees
Nov 30 - Dec 1
Prospect Berkshires
A room with a round table and two chairs, a window with a view of trees and a building, and an air conditioning unit.

17. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (713 reviews)
"It was super clean and safe"
United States
Fernando
The price is CA $78
CA $88 total
includes taxes & fees
Dec 2 - Dec 3
Econo Lodge Lee - Great Barrington
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

18. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,006 reviews)
"Enjoyed staying in the old hotel and loved the large porch with the bar to relax on."
United States
Mallory
The price is CA $220
CA $315 total
includes taxes & fees
Nov 12 - Nov 13
The Red Lion Inn
A dining area with round tables set for two, a fireplace, and a mural on the wall.

19. The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (96 reviews)
"Lovely property.unique historic buildings and rooms with updated amenities! Quiet and peaceful beautiful dinner!"
United States
mary ellen
The price is CA $405
CA $489 total
includes taxes & fees
Nov 6 - Nov 7
The Old Inn On The Green
A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

20. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,000 reviews)
"Nice place to stay"
United States
Michael
The price is CA $163
CA $210 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
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

The Whitlock

The Whitlock

10/10 Excellent
"Logan, the Innkeeper, was fantastic and so helpful. The property is beautiful! Spacious rooms, fabulous location. The restaurant/bar was closed onsite in October - so FYI on that. Overall, a wonderful stay!"
Kristina 1-night trip
Posted 5 hours ago
The Whitlock

Find out more about Sheffield

Sheffield Resorts information

Number of reviews
5,655
Accommodation
4 Resorts
Lowest Price
CA $88
Highest Price
CA $572

Frequently asked questions

What can I expect from a resort vacation in Sheffield?
Longing for a relaxing getaway? Indulge in all the comforts of a resort, where you can find everything you need for your stay from convenient food and drink options to activities and shopping. Browse the resort options in the area and discover the right one for you, whether you envision yourself sipping drinks by a sprawling pool or hitting the golf course for an afternoon game.
What's a top resort in Sheffield?
Here are our top-rated resorts around Sheffield: Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA - 12.1 mi (19.5 km) from Sheffield. Has a fitness center. Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA - 12.1 mi (19.5 km) from Sheffield. Enjoy the fitness center. July 12-19 2026: Resort with 2 bedrooms and AC in the delightful Berkshires - 12.3 mi (19.8 km) from Sheffield. Amenities include a fitness center. Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA - 12.1 mi (19.5 km) from Sheffield. Access to a fitness center.
What can I do in Sheffield?
Housatonic River, Suter Farm, and Ashley House are a few of the interesting sights to visit. Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary are a few additional attractions in the area that you might like.
What's the weather like in Sheffield?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around Sheffield?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 22 mi (35.4 km) from the city center. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.9 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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