The Best Sheffield, MA Resorts from $62

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Recommended hotels in Sheffield

1. Wilder House Berkshires

Sheffield

Liliana

$182 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

2. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

$366 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

Downtown Great Barrington

Lynne

$76 nightly

Nov 29 - Nov 30

Total with taxes and fees

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

4. Monument Mountain Motel

Great Barrington

Andrea

$67 nightly

Nov 8 - Nov 9

Total with taxes and fees

A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

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

Great Barrington

Cynthia

$83 nightly

Dec 3 - Dec 4

Total with taxes and fees

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

Great Barrington

Sherry

$79 nightly

Nov 6 - Nov 7

Total with taxes and fees

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

Great Barrington

Md

$161 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

8. East Rock Inn

Great Barrington

Sharon

$120 nightly

Dec 6 - Dec 7

Total with taxes and fees

A picnic table with a red umbrella in a grassy area with trees in the background.

9. The Little Lion

Great Barrington

David

$86 nightly

Nov 8 - Nov 9

Total with taxes and fees

A covered porch with white railings and rocking chairs.

10. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

$105 nightly

Nov 6 - Nov 7

Total with taxes and fees

A house with a stone patio and wooden stools.

11. Little Cat Lodge

Copake Falls

Stacy

$147 nightly

Dec 6 - Dec 7

Total with taxes and fees

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Great Barrington

Deborah S.

$96 nightly

Nov 12 - Nov 13

Total with taxes and fees

A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

13. the Alander

Copake

Luis

$165 nightly

Nov 20 - Nov 21

Total with taxes and fees

A wooden cabin with a deck, large windows, and outdoor seating.

14. The Cozy Cat Motel

Copake Falls

$149 nightly

Nov 8 - Nov 9

Total with taxes and fees

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

15. Blackberry River Inn

Norfolk

Melanie

$174 nightly

Nov 8 - Nov 9

Total with taxes and fees

A wooden boat on calm water with a house in the background.

16. Prospect Berkshires

Egremont

Sunny

$295 nightly

Nov 30 - Dec 1

Total with taxes and fees

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

Lee

Fernando

$56 nightly

Nov 30 - Dec 1

Total with taxes and fees

A straw hat, sunglasses, and two drinks on a striped towel by a body of water.

18. The Red Lion Inn

Stockbridge

Mallory

$195 nightly

Nov 12 - Nov 13

Total with taxes and fees

A white two-story house with a front door, windows, and a chimney.

19. The Old Inn On The Green

Great Barrington

mary ellen

$319 nightly

Nov 6 - Nov 7

Total with taxes and fees

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

South Lee

Michael

$135 nightly

Nov 8 - Nov 9

Total with taxes and fees

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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.

Top reviews in Sheffield

Wilder House Berkshires

Sheffield

10/10 Excellent

Liliana

Quality Inn Great Barrington

Downtown Great Barrington

10/10 Excellent

Andrew

Monument Mountain Motel

Great Barrington

10/10 Excellent

We have stayed here a half dozen times, and if you are simply looking for a clean place to lay your head for the night with no frills, then this place is perfect! The rooms have always been clean and everything in good working order. So what that they don't have breakfast...there is an AMAZING breakfast spot right across the street. Take HALF the money you saved by avoiding big name hotels and you'll get a much better breakfast! We've never had noise issues, never felt "unsafe", and the staff is...

Anthony

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

10/10 Excellent

We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!

Anonymous traveler

Locust Tree Bed and Breakfast LLC

East Canaan

10/10 Excellent

rose

Little Cat Lodge

Copake Falls

10/10 Excellent

Elisabeth

The Little Lion

Great Barrington

10/10 Excellent

Hong

Blackberry River Inn

Norfolk

10/10 Excellent

Brandon

Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

10/10 Excellent

Kunal and his family were very hospitable and helpful, making my stay very comfortable in Great Barrington in the heart of Berkshire County! Their accommodations are quite clean and truly have all you might need for your stay and the price was also the best I found with good quality! They also have a nice continental breakfast...where I met a number of families...traveling for the school vacation week...to be close to the mountains and skiing. I was traveling for business so Great Barrington...

Travelling NP

The Old Inn On The Green

Great Barrington

10/10 Excellent

Rishi

A bedroom with a large bed, a chair, and a window with curtains.

The White Hart

Salisbury

10/10 Excellent

We enjoyed our stay at the White Hart. We got a room in the back of the building overlooking a garden. We loved sitting out there and relaxing. The room was a nice size and comfortable. The complementary breakfast provided a good selection and was tasty. The lobby is a nice place to have coffee or wine. The chairs are everywhere and make it a nice place to relax. Service was friendly and attentive and Provisions provides excellent sandwiches. We were also able to park right outside our...

thomas

A lodge with a large building and a dock by a lake, surrounded by forest.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

Sheila

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

South Lee

10/10 Excellent

I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...

David

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

The Red Lion Inn

Stockbridge

10/10 Excellent

Michael

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.

Best Resorts in Sheffield

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Check prices for these dates

Recommended hotels in Sheffield

1. Wilder House Berkshires

2. Cheerful 3-bedroom cottage with woodstove

3. Quality Inn Great Barrington

4. Monument Mountain Motel

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

6. Travelodge by Wyndham Great Barrington Berkshires

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

8. East Rock Inn

9. The Little Lion

10. Locust Tree Bed and Breakfast LLC

11. Little Cat Lodge

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

13. the Alander

14. The Cozy Cat Motel

15. Blackberry River Inn

16. Prospect Berkshires

17. Econo Lodge Lee - Great Barrington

18. The Red Lion Inn

19. The Old Inn On The Green

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

Learn more about Sheffield

Top reviews in Sheffield

Wilder House Berkshires

10/10 Excellent

Frequently Asked Questions

What can I expect from a resort vacation in Sheffield?

What's a top resort in Sheffield?

What can I do in Sheffield?

What's the weather like in Sheffield?

What's the best way to get to and around Sheffield?

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