Top 10 Hotels in Sheffield, MA from ￥10,568 - Competitive Prices

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

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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

￥25,904

￥28,935 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.

A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.

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

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

2. Quality Inn Great Barrington

Downtown Great Barrington

Scott Patterson

￥11,959

￥13,358 total

includes taxes & fees

Nov 5 - Nov 6

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

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

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

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

Great Barrington

￥22,708

￥25,365 total

includes taxes & fees

Nov 2 - Nov 3

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

A kitchenette with a microwave, coffee maker, and coffee cups.

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

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

￥14,071

￥15,718 total

includes taxes & fees

Nov 15 - Nov 16

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

A hotel room with a wooden dresser, a television, a microwave, and a mirror.

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

Andrea

￥9,461

￥10,568 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.

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

6. East Rock Inn

Great Barrington

ERIK

￥19,232

￥21,482 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.

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

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

A motel with a two-story structure, multiple rooms with red doors, and a central staircase.

7. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

￥12,488

￥13,949 total

includes taxes & fees

Oct 18 - Oct 19

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 wall with a white pendant light fixture.

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

8. Prospect Berkshires

Egremont

Conor

￥44,815

￥55,355 total

includes taxes & fees

Nov 10 - Nov 11

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

A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

A house with a stone patio and wooden stools.

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

9. Little Cat Lodge

Copake Falls

Stacy

￥21,402

￥23,970 total

includes taxes & fees

Nov 16 - Nov 17

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

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

A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

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

10. The Old Inn On The Green

Great Barrington

Catherine

￥45,843

￥55,318 total

includes taxes & fees

Nov 1 - Nov 2

A large house with a balcony and a grassy yard.

A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

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

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.

11. The Little Lion

Great Barrington

Lidia

￥16,361

￥18,276 total

includes taxes & fees

Oct 18 - Oct 19

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

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

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

A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.

12. Blackberry River Inn

Norfolk

Donna

￥30,035

￥34,540 total

includes taxes & fees

Oct 18 - Oct 19

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

A dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.

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

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.

13. The White Hart

Salisbury

William

￥48,805

￥56,127 total

includes taxes & fees

Nov 15 - Nov 16

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

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

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

A covered porch with white railings and rocking chairs.

14. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

￥16,598

￥19,088 total

includes taxes & fees

Oct 18 - Oct 19

A building with a porch and multiple windows, surrounded by purple flowers.

A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

A café with a display case, a frozen food section, and a marketplace sign.

A living room with a sofa, armchair, coffee table, and a patterned rug.

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

South Lee

Michael

￥18,495

￥23,749 total

includes taxes & fees

Oct 26 - Oct 27

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

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

A dog standing at a door entrance with a wooden floor and a mat with paw prints.

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.

16. the Alander

Copake

Luis

￥26,083

￥29,213 total

includes taxes & fees

Oct 31 - Nov 1

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

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

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

A bar with wooden floors and shelves filled with bottles.

17. The Red Lion Inn

Stockbridge

Stephan

￥24,900

￥35,667 total

includes taxes & fees

Nov 3 - Nov 4

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

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

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

18. Quality Inn Lee - Lenox South

Lee

Lucinda

￥14,646

￥16,360 total

includes taxes & fees

Nov 5 - Nov 6

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

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.

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

19. Granville House

Housatonic

Cynthia

￥40,152

￥44,850 total

includes taxes & fees

Oct 25 - Oct 26

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

A compact kitchen with a wooden countertop, a coffee machine, and a small shelf with a hair dryer and cups.

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

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

20. The Brooks Motel

Hillsdale

Nelson

￥23,048

￥25,814 total

includes taxes & fees

Oct 18 - Oct 19

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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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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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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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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

Prospect Berkshires

10/10 Excellent

"Peaceful place. Quiet and relaxing. Minimalistic luxury"

The Red Lion Inn

10/10 Excellent

"Wonderful"

Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"Sitting around the fire pit after a long day of leaf peeping was glorious..."

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

10/10 Excellent

"New hotel with clean"

the Alander

8/10 Good

"Super cute, fairly clean and such a lovely breakfast!"

The Cornell Inn, Lenox & The Berkshires

8/10 Good

"Our room was very nice with a comfortable bed, but the door to the room did not fit properly so lots of light came through the edges. Also we could hear the guests above us ( we were on first floor in carriage house) tramping around at 6:00 am. It would help to carpet the floors. The breakfast, which was much hyped, was only okay. The ingredients were nothing special, for example the bread used for toast appeared to be off the grocery store shelf."

Quality Inn Great Barrington

10/10 Excellent

"good location, friendly helpful staff"

Quality Inn Lee - Lenox South

8/10 Good

"Had a comfortable stay."

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Nice place to stay"

More cheap stays in Sheffield

Quality Inn Great Barrington

372 Main Street Great Barrington MA

￥11,959

￥13,358 total

Nov 5 - Nov 6

includes taxes & fees

8.6/10 Excellent! (1,001 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

￥12,488

￥13,949 total

Oct 18 - Oct 19

includes taxes & fees

7.6/10 Good! (926 reviews)

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

￥14,646

￥16,360 total

Nov 5 - Nov 6

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

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

1055 South Street Pittsfield MA

￥15,652

￥17,483 total

Nov 15 - Nov 16

includes taxes & fees

9.4/10 Exceptional! (238 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

￥16,756

￥18,716 total

Nov 1 - Nov 2

includes taxes & fees

The Whitlock

16 Church St Lenox MA

￥20,079

￥22,428 total

Nov 1 - Nov 2

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 ￥10,568

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. Prospect Berkshires

9. Little Cat Lodge

10. The Old Inn On The Green

11. The Little Lion

12. Blackberry River Inn

13. The White Hart

14. Locust Tree Bed and Breakfast LLC

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

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

Bartholomew's Cobble

Bartholomews Cobble

Drury Preserve

Lime Kiln Farm Wildlife Sanctuary

Learn more about Sheffield

Top Sheffield Hotel Reviews

Prospect Berkshires

The Red Lion Inn

Courtyard by Marriott Lenox Berkshires

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

the Alander

The Cornell Inn, Lenox & The Berkshires

Quality Inn Great Barrington

Quality Inn Lee - Lenox South

Holiday Inn Club Vacations Oak 'n Spruce Resort

More cheap stays in Sheffield

Quality Inn Great Barrington

Howard Johnson by Wyndham Lenox

Quality Inn Lee - Lenox South

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

The Yankee Inn

The Whitlock

Frequently asked questions

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