Top 10 Hotels in Sheffield, MA from ￥10,528 - Competitive Prices

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Our top choices for Sheffield hotels

1. Wilder House Berkshires

Sheffield

Liliana

￥28,827 total

includes taxes & fees

Oct 29 - Oct 30

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

2. Quality Inn Great Barrington

Downtown Great Barrington

Lynne

￥13,210 total

includes taxes & fees

Nov 22 - Nov 23

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

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

Great Barrington

Md

￥25,270 total

includes taxes & fees

Nov 3 - Nov 4

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

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

Great Barrington

Cynthia

￥15,832 total

includes taxes & fees

Nov 12 - Nov 13

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

5. Monument Mountain Motel

Great Barrington

Andrea

￥10,528 total

includes taxes & fees

Nov 1 - Nov 2

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

6. East Rock Inn

Great Barrington

Sharon

￥22,552 total

includes taxes & fees

Nov 28 - Nov 29

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

7. Little Cat Lodge

Copake Falls

Stacy

￥26,828 total

includes taxes & fees

Nov 2 - Nov 3

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

8. Prospect Berkshires

Egremont

Conor

￥55,149 total

includes taxes & fees

Nov 16 - Nov 17

A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

9. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Sherry

￥13,898 total

includes taxes & fees

Oct 31 - Nov 1

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

10. The White Hart

Salisbury

William

￥54,180 total

includes taxes & fees

Nov 15 - Nov 16

A large house with a balcony and a grassy yard.

11. The Little Lion

Great Barrington

David

￥18,207 total

includes taxes & fees

Oct 29 - Oct 30

A dining area with round tables set for two, a fireplace, and a mural on the wall.

12. The Old Inn On The Green

Great Barrington

mary ellen

￥55,112 total

includes taxes & fees

Nov 3 - Nov 4

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

13. Blackberry River Inn

Norfolk

Melanie

￥32,003 total

includes taxes & fees

Nov 3 - Nov 4

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

14. the Alander

Copake

Luis

￥29,104 total

includes taxes & fees

Nov 20 - Nov 21

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

15. The Red Lion Inn

Stockbridge

Mallory

￥34,181 total

includes taxes & fees

Nov 8 - Nov 9

A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

16. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

￥19,016 total

includes taxes & fees

Nov 3 - Nov 4

A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

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

South Lee

Michael

￥25,087 total

includes taxes & fees

Nov 2 - Nov 3

18. Quality Inn Lee - Lenox South

Lee

James

￥16,298 total

includes taxes & fees

Nov 17 - Nov 18

A dining table with pastries, a coffee pot, and a vase of sunflowers.

19. Granville House

Housatonic

Cynthia

￥44,860 total

includes taxes & fees

Nov 3 - Nov 4

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

20. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Gustavo

￥19,289 total

includes taxes & fees

Nov 22 - Nov 23

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Stay near popular Sheffield attractions

Ashley House

Built in 1735, the Ashley House is where Elizabeth Freeman successfully sued for her freedom, helping end slavery in Massachusetts. Tour the historic rooms and learn about this pivotal chapter in American history.

See properties

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 Sheffield Hotel Reviews

Berkshire Mountain Lodge

8/10 Good

"Clean and comfortable"

The Yankee Inn

8/10 Good

"We stayed at the Yankee Inn for 1 night. We had no problems with check-in. Our room was clean but outdated except the bathroom which was very nice. Good water pressure in the shower and the bed was comfortable. Unfortunately, due to myself not feeling well, we did not use the hot tub, enjoy the fire pit or try breakfast all of which would have likely improved our stay. Maybe next time!"

Quality Inn Lee - Lenox South

8/10 Good

"Bed was comfortable, breakfast was fine, and it's a generally attractive property. We were in room 125, which was awkwardly laid out. The toilet was mashed up against the sink, and the desk was opposite the foot of the bed, making a traffic bottleneck. I'd guess 126 is the same, but hopefully the rest of the rooms weren't."

More cheap stays in Sheffield

Quality Inn Great Barrington

372 Main Street Great Barrington MA

￥11,827

￥13,210 total

Nov 22 - Nov 23

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

Frequently asked questions

Where is the best place to stay in Sheffield?

Wilder House Berkshires is one of the top choices for your stay based on our traveler data. This B&B offers free breakfast and free parking. Other good choices for your trip to the area are Berkshire Mountain Lodge and Quality Inn Great Barrington. See all available top hotels, or vacation rentals in Sheffield.

What are some of the best vacation home rentals that Sheffield has to offer?

Antique Farmhouse Totally Restored: This highly rated vacation home rental in Sheffield is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. See all vacation rentals in Sheffield.

If I need to cancel my hotel reservation in Sheffield, will I receive a refund?

Yes! The majority of hotel room reservations are refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your check-in date. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.

Where can I learn more about changing or cancelling my trip to Sheffield?

To access more information about changing or cancelling your trip to Sheffield, go to https://www.expedia.com/service/.

What's the best place to stay near Ashley House?

Sheffield 1802 House is one of the top choices for your stay based on our traveler data, and this 3.5-star B&B offers free breakfast and free parking. It's located 3.2 mi (5.1 km) from Ashley House. Another good option is Locust Tree Bed and Breakfast, located 3.8 mi (6.2 km) away.

What about the best place to stay near Magnolia Bluffs Casino?

One of the top choices for your stay is Sheffield 1802 House, located 1.6 mi (2.6 km) from Magnolia Bluffs Casino, and this 3.5-star B&B offers free breakfast and free parking.

What are some accommodations with pools in Sheffield?

Berkshire Mountain Lodge: Provides free self parking, an indoor pool, and complimentary wireless internet access. The Yankee Inn and The Red Lion Inn are a couple of other choices that offer an onsite pool. View all hotels with pools in Sheffield.

What is the best accommodation for staying close to Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

What's it like staying in Sheffield?

Visitors can enjoy all that Sheffield has to offer including the casinos and local tours. In Sheffield, there are 32 hotels and other accommodations to choose from. Find out more about Sheffield.

What should I see while I'm in Sheffield?

Favorite places to visit include Housatonic River, Suter Farm, and Ashley House. A couple of additional sights to add to your agenda are Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary. Check out what more to see and do in Expedia's Sheffield guide.

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.

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Find hotels in Sheffield, MA from ￥10,528

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Our top choices for Sheffield hotels

1. Wilder House Berkshires

2. Quality Inn Great Barrington

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

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

5. Monument Mountain Motel

6. East Rock Inn

7. Little Cat Lodge

8. Prospect Berkshires

9. Travelodge by Wyndham Great Barrington Berkshires

10. The White Hart

11. The Little Lion

12. The Old Inn On The Green

13. Blackberry River Inn

14. the Alander

15. The Red Lion Inn

16. Locust Tree Bed and Breakfast LLC

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

18. Quality Inn Lee - Lenox South

19. Granville House

20. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Stay near popular Sheffield attractions

Ashley House

Learn more about Sheffield

Top Sheffield Hotel Reviews

Berkshire Mountain Lodge

More cheap stays in Sheffield

Quality Inn Great Barrington

Frequently asked questions

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