Top 10 Hotels in Sheffield, MA from ￥10,605 - 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 bedroom with a large bed, a dresser, a chair, and a mirror.

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

1. Wilder House Berkshires

Sheffield

Mark

￥29,467

￥32,915 total

includes taxes & fees

Nov 8 - Nov 9

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

2. Quality Inn Great Barrington

Downtown Great Barrington

Joan

￥12,312

￥13,753 total

includes taxes & fees

Nov 10 - Nov 11

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.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

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

Kelly

￥22,746

￥25,408 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 coffee station with two coffee machines and a variety of coffee pods and cups.

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

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

Great Barrington

Maria Dulce

￥13,167

￥14,709 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.

A motel with a parking lot and several cars parked.

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

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

5. Monument Mountain Motel

Great Barrington

Andrea

￥9,495

￥10,605 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.

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

6. East Rock Inn

Great Barrington

ERIK

￥23,026

￥25,720 total

includes taxes & fees

Nov 1 - Nov 2

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

Mark

￥12,509

￥13,973 total

includes taxes & fees

Oct 18 - Oct 19

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

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.

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

8. Prospect Berkshires

Egremont

Conor

￥43,361

￥53,750 total

includes taxes & fees

Nov 4 - Nov 5

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

9. Little Cat Lodge

Copake Falls

Stacy

￥24,083

￥26,972 total

includes taxes & fees

Nov 12 - Nov 13

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

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.

10. The Little Lion

Great Barrington

Lidia

￥16,388

￥18,305 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 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.

11. Blackberry River Inn

Norfolk

Donna

￥30,085

￥34,597 total

includes taxes & fees

Oct 25 - Oct 26

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

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.

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

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

12. The Old Inn On The Green

Great Barrington

Catherine

￥45,919

￥55,410 total

includes taxes & fees

Nov 2 - Nov 3

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

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.

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

￥86,287

￥99,230 total

includes taxes & fees

Nov 14 - Nov 15

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 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.

14. the Alander

Copake

Joseph

￥26,918

￥30,149 total

includes taxes & fees

Oct 20 - Oct 21

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

A covered porch with white railings and rocking chairs.

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

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

15. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

￥16,626

￥19,120 total

includes taxes & fees

Oct 18 - Oct 19

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 bar with wooden floors and shelves filled with bottles.

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

16. The Red Lion Inn

Stockbridge

Stephan

￥24,942

￥35,727 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

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

South Lee

Jared

￥18,526

￥23,790 total

includes taxes & fees

Oct 28 - Oct 29

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

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

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

18. Quality Inn Lee - Lenox South

Lee

Christine

￥14,670

￥16,386 total

includes taxes & fees

Nov 8 - Nov 9

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

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

Cynthia

￥40,218

￥44,924 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 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.

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

20. The Brooks Motel

Hillsdale

Nelson

￥23,086

￥25,855 total

includes taxes & fees

Oct 15 - Oct 16

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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

Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"Highly recommended, comfortable bed and beautiful cozy hotel"

The Yankee Inn

10/10 Excellent

"This is a gem of a small hotel/motel. Super comfortable rooms, updated bathrooms, and well done self serve breakfast included. Also has an indoor pool and an outdoor pool during the season. And a very nice hiking trail off of the back. An excellent change from the Run of the middle courtyard Marriott!"

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

10/10 Excellent

"Very clean and nice options for breakfast. Helpful staff."

Berkshires Untold

8/10 Good

"Enjoyed the view and the aesthetic"

The Red Lion Inn

8/10 Good

"I enjoyed my stay, lovely little town. The Inn is beginning to show some signs of wear. A broken tile (baseboard) by the tub. However, staff pleasant and helpful. Excellent restaurants."

Berkshire Mountain Lodge

10/10 Excellent

"Great to have a whole suite not just a room. Even though a little outdated still very nice. Downsides were an absence of food vending machines for when you need a quick snack and don’t want to leave, and hot tub was under renovations which we weren’t made aware of until online check in. Overall very happy."

Quality Inn Lee - Lenox South

8/10 Good

"Short stay for business, but good value and a well-kept facility. No issues, Will stay there again."

Quality Inn Great Barrington

10/10 Excellent

"Beds were comfortable, room was clean, train was not often"

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"It's a perfect stop on our little Berkshires trip. The Inn had everything we needed and more. The property was beautiful, and the staff was beyond helpful. We will certainly be back."

More cheap stays in Sheffield

Quality Inn Great Barrington

372 Main Street Great Barrington MA

￥12,312

￥13,753 total

Nov 10 - Nov 11

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

￥12,509

￥13,973 total

Oct 18 - Oct 19

includes taxes & fees

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

￥14,670

￥16,386 total

Nov 8 - Nov 9

includes taxes & fees

8.6/10 Excellent! (1,005 reviews)

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

1055 South Street Pittsfield MA

￥15,676

￥17,509 total

Nov 11 - Nov 12

includes taxes & fees

9.2/10 Wonderful! (237 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

￥16,784

￥18,747 total

Nov 1 - Nov 2

includes taxes & fees

9.2/10 Wonderful! (1,010 reviews)

The Whitlock

16 Church St Lenox MA

￥22,484

￥25,115 total

Nov 2 - Nov 3

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 ￥10,605

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 Little Lion

11. Blackberry River Inn

12. The Old Inn On The Green

13. The White Hart

14. the Alander

15. Locust Tree Bed and Breakfast LLC

16. The Red Lion Inn

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

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

Courtyard by Marriott Lenox Berkshires

The Yankee Inn

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

Berkshires Untold

The Red Lion Inn

Berkshire Mountain Lodge

Quality Inn Lee - Lenox South

Quality Inn Great Barrington

The Cornell Inn, Lenox & The Berkshires

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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