Top 10 Hotels in Sheffield, MA from ￥10,634 - Competitive Prices

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

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Our top choices for Sheffield hotels

A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.

1. Wilder House Berkshires

Sheffield

Mark

￥32,479

￥36,279 total

includes taxes & fees

Oct 25 - Oct 26

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

A hotel room with a bathroom, a bed, a desk, and a nightstand.

A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

A Quality Inn sign, a brick building, and a parking lot with cars.

2. Quality Inn Great Barrington

Great Barrington

Joan

￥15,918

￥17,780 total

includes taxes & fees

Oct 21 - Oct 22

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

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

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

Great Barrington

Bruce

￥30,632

￥34,216 total

includes taxes & fees

Oct 5 - Oct 6

A modern hotel lobby with seating areas, tables, and a reception desk.

A hotel room with two beds, a desk, a TV, and a window with curtains.

A breakfast area with a counter, coffee machine, and a display of pastries.

A coffee station with two coffee machines and a variety of coffee pods and cups.

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

Great Barrington

Maria Dulce

￥18,727

￥20,918 total

includes taxes & fees

Oct 19 - Oct 20

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

A motel with a parking lot and several cars parked.

A row of white plastic chairs on a covered outdoor area with a white building in the background.

A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

5. Monument Mountain Motel

Great Barrington

Victor

￥10,764

￥12,023 total

includes taxes & fees

Oct 26 - Oct 27

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

A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

A grassy outdoor area with four blue Adirondack chairs arranged in a circle.

6. East Rock Inn

Great Barrington

ERIK

￥22,499

￥25,132 total

includes taxes & fees

Oct 19 - Oct 20

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

A living room with a patterned carpet, two sofas, a dining table, and chairs.

A circular pool with a tiled edge, surrounded by a concrete deck and a grassy area with chairs and a small shed.

A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

7. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

￥12,432

￥13,886 total

includes taxes & fees

Oct 1 - Oct 2

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

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

A house with a stone patio and wooden stools.

8. Little Cat Lodge

Copake Falls

Kees

￥28,185

￥31,566 total

includes taxes & fees

Oct 4 - Oct 5

A rustic wooden building labeled 'GEDNEY FARM' with a signboard indicating 'SERVING DINNER WED-FRI 5:00-9:00pm'.

A wooden sign with "GEDNEY FARM" written on it, surrounded by lush greenery and purple flowers.

An outdoor patio with wooden tables and chairs, surrounded by greenery.

A rustic barn-style venue with round tables and chairs, string lights, and a central bar area.

9. Gedney Farm

Great Barrington

Terri

￥31,740

￥34,819 total

includes taxes & fees

Oct 8 - Oct 9

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

A wooden deck with a dog silhouette against a backdrop of autumn foliage.

A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.

10. Prospect Berkshires

Egremont

Conor

￥65,859

￥78,838 total

includes taxes & fees

Oct 1 - Oct 2

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

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

A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.

11. The Old Inn On The Green

Great Barrington

Catherine

￥51,932

￥62,666 total

includes taxes & fees

Oct 1 - Oct 2

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

A room with a fireplace, two striped armchairs, and a floral drape.

A cozy living room with floral wallpaper, a sofa, a coffee table, and two lamps.

A grand hallway with a chandelier, a staircase, and a table with flowers.

12. Blackberry River Inn

Norfolk

Brian

￥23,606

￥27,146 total

includes taxes & fees

Oct 8 - Oct 9

A large house with a balcony and a grassy yard.

A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.

A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

A two-story building with a gabled roof and a chimney.

13. The Little Lion

Great Barrington

Lidia

￥16,288

￥18,193 total

includes taxes & fees

Oct 18 - Oct 19

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

A framed painting of a white horse on a wooden dresser, a white fireplace with a black mantle, and two green vases with white flowers on the wall.

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

A covered porch with a dining area, a sofa, and decorative wall art.

14. The White Hart

Salisbury

William

￥70,887

￥81,520 total

includes taxes & fees

Oct 7 - Oct 8

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

A bedroom with a wooden bed, two bedside tables, a window with curtains, and a radiator.

A two-story building with a flat roof, solar panels, and a small patio area.

A dining room with a wooden table, chairs, a vase with flowers, and red curtains.

15. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

￥16,524

￥19,003 total

includes taxes & fees

Oct 4 - Oct 5

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

A modern living room with a sofa, armchair, and coffee table. There is a bed with a headboard and pillows, a lamp, and a shelf with items.

A bar area with a green counter, two pendant lights, and shelves stocked with bottles.

A dining table set with plates of food, wine glasses, and bottles, with a chandelier above and shelves above holding glasses and bottles.

16. the Alander

Copake

Thomas

￥22,740

￥25,470 total

includes taxes & fees

Oct 4 - Oct 5

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

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

A bar with wooden floors and shelves filled with bottles.

17. The Red Lion Inn

Stockbridge

Stephan

￥27,974

￥39,064 total

includes taxes & fees

Oct 19 - Oct 20

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

18. Quality Inn Lee - Lenox South

Lee

Christine

￥17,256

￥19,274 total

includes taxes & fees

Oct 21 - Oct 22

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

A large, two-story white building with a symmetrical facade, columns, and a central entrance.

A bedroom with a wooden bed, bedside tables, a desk, and a chair.

A pool table in a room with a patterned rug, a shelf with decorative items, and a window with a view of greenery.

19. Granville House

Housatonic

Nicole

￥43,277

￥48,341 total

includes taxes & fees

Oct 12 - Oct 13

A modern bedroom with a large bed, two bedside tables, and a textured wall behind the bed.

A dining area with a wooden table, chairs, and a colorful striped rug.

A snow-covered landscape with a house and a sign that reads "the brooks".

A living room with a sofa, a coffee table, a fireplace, and a ceiling fan.

20. The Brooks Motel

Hillsdale

Nelson

￥21,109

￥23,644 total

includes taxes & fees

Oct 5 - Oct 6

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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.

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Thom Reed UFO Monument Park

8.0/10 (1 review)

America's first officially documented UFO encounter is commemorated at this riverside park in Sheffield. Explore plaques about the Reed family's 1969 experience while enjoying Housatonic River views.

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Bartholomews Cobble

Twin rocky knolls form this National Natural Landmark, home to one of North America's most diverse fern collections. Explore five miles of trails through forests and riverbanks for exceptional wildlife viewing.

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Drury Preserve

Explore diverse ecosystems along a serene 2.4-mile trail through hemlock forests and calcareous wetlands. Cross wooden boardwalks to a tranquil pond where great blue herons and other wildlife await.

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Bartholomew's Cobble

10.0/10 (1 review)

This National Natural Landmark features twin rocky knolls and North America's most diverse fern collection. Explore its trails through varied ecosystems while watching for peregrine falcons and rare plants.

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Lime Kiln Farm Wildlife Sanctuary

This wildlife sanctuary showcases diverse plant species across limestone ridges and conifer forests. Explore trails to spot numerous butterfly species and Pileated Woodpeckers in the tranquil Berkshires landscape.

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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

Top Sheffield Hotel Reviews

Berkshires Untold

8/10 Good

"All was good for the price. Great location. Gentlemen at the bar and check-in was very pleasant and helpful. Dinner could have been better prepared."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"Most helpful staff, very clean and best breakfast around"

The Red Lion Inn

8/10 Good

"Very unique property. Great nostalgic atmosphere."

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Wonderful resort"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"This was a nice clean convenient hidden gem. Situated on the water, a little cool right now , but the beginning of fall follege was very pretty. Staff was polite and helpful. I would return."

Quality Inn Lee - Lenox South

10/10 Excellent

"Very sweet desk clerk answered my question about late arrival quickly and cheerfully."

Quality Inn Great Barrington

10/10 Excellent

"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."

The Yankee Inn

10/10 Excellent

"Nice room. Exceptionally clean. Great staff"

Hampton Inn & Suites Berkshires-Lenox

8/10 Good

"Breakfast was great"

More cheap stays in Sheffield

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

￥12,432

￥13,886 total

Oct 1 - Oct 2

includes taxes & fees

7.6/10 Good! (917 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

￥15,918

￥17,780 total

Oct 21 - Oct 22

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

1055 South Street Pittsfield MA

￥16,681

￥18,633 total

Oct 29 - Oct 30

includes taxes & fees

9.4/10 Exceptional! (221 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

￥16,996

￥18,985 total

Oct 27 - Oct 28

includes taxes & fees

9.2/10 Wonderful! (1,016 reviews)

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

￥17,256

￥19,274 total

Oct 21 - Oct 22

includes taxes & fees

8.6/10 Excellent! (1,010 reviews)

The Whitlock

16 Church St Lenox MA

￥23,676

￥26,447 total

Oct 28 - Oct 29

includes taxes & fees

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 ￥10,634

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Sheffield

Check prices for these dates

Filter by

Property class

Guest rating

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. Travelodge by Wyndham Great Barrington Berkshires

8. Little Cat Lodge

9. Gedney Farm

10. Prospect Berkshires

11. The Old Inn On The Green

12. Blackberry River Inn

13. The Little Lion

14. The White Hart

15. Locust Tree Bed and Breakfast LLC

16. the Alander

17. The Red Lion Inn

18. Quality Inn Lee - Lenox South

19. Granville House

20. The Brooks Motel

Stay near popular Sheffield attractions

Ashley House

Thom Reed UFO Monument Park

Bartholomews Cobble

Drury Preserve

Bartholomew's Cobble

Lime Kiln Farm Wildlife Sanctuary

Learn more about Sheffield

Top Sheffield Hotel Reviews

Berkshires Untold

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

The Red Lion Inn

Holiday Inn Club Vacations Oak 'n Spruce Resort

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Quality Inn Lee - Lenox South

Quality Inn Great Barrington

The Yankee Inn

Hampton Inn & Suites Berkshires-Lenox

More cheap stays in Sheffield

Howard Johnson by Wyndham Lenox

Quality Inn Great Barrington

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

The Yankee Inn

Quality Inn Lee - Lenox South

The Whitlock

Frequently asked questions

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