Top 10 Hotels in Sheffield, MA from ￥10,627 - 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 bedroom with a large bed, a dresser, a chair, and a mirror.

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

￥32,461

￥36,258 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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.

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

Great Barrington

Bruce

￥30,615

￥34,196 total

includes taxes & fees

Oct 4 - Oct 5

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 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'.

3. Quality Inn Great Barrington

Great Barrington

Joan

￥15,909

￥17,771 total

includes taxes & fees

Oct 18 - Oct 19

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

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.

A motel with a parking lot and several cars parked.

4. Monument Mountain Motel

Great Barrington

Victor

￥10,758

￥12,016 total

includes taxes & fees

Oct 25 - Oct 26

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.

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

Great Barrington

Maria Dulce

￥18,716

￥20,905 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 hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

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

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

6. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Kevin

￥11,796

￥13,177 total

includes taxes & fees

Sep 29 - Sep 30

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

A covered porch with white railings and rocking chairs.

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.

7. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

￥16,514

￥18,991 total

includes taxes & fees

Sep 29 - Sep 30

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.

8. Little Cat Lodge

Copake Falls

Kees

￥28,169

￥31,550 total

includes taxes & fees

Sep 29 - Sep 30

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

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

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.

9. Blackberry River Inn

Norfolk

Brian

￥20,289

￥23,333 total

includes taxes & fees

Oct 6 - Oct 7

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.

10. The Little Lion

Great Barrington

Lidia

￥16,278

￥18,183 total

includes taxes & fees

Oct 18 - Oct 19

A round wooden table with two wine glasses and a green bottle, set against a window with a view of a blue railing and trees.

A hotel reception desk with an orange counter, a computer, a beverage cooler, and framed awards on the wall.

A hotel room with a bed, a desk, and two wall-mounted lamps.

A motel with multiple rooms, a well-maintained lawn, and a stone pathway.

11. Econo Lodge Lee - Great Barrington

Lee

Anna

￥10,454

￥11,677 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.

12. East Rock Inn

Great Barrington

ERIK

￥22,486

￥25,117 total

includes taxes & fees

Oct 12 - Oct 13

A group of people performing yoga in an outdoor setting with grass and trees.

A reception desk with a framed floral painting, a deer head, and a sign about pets.

A motel with a row of rooms, a parking lot, and a hilly backdrop.

A hotel room with a flat-screen TV, a microwave, a refrigerator, a wooden dresser, a bedside lamp, and a framed picture on the wall.

13. Pleasant Valley Motel West Stockbridge

West Stockbridge

James

￥9,688

￥10,627 total

includes taxes & fees

Sep 29 - Sep 30

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

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

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

14. Quality Inn Lee - Lenox South

Lee

Wendy

￥17,246

￥19,263 total

includes taxes & fees

Oct 19 - Oct 20

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 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.

15. the Alander

Copake

Thomas

￥22,727

￥25,454 total

includes taxes & fees

Sep 30 - Oct 1

16. Berkshire Travel Lodge

Austerlitz

Kris

￥10,615

￥11,889 total

includes taxes & fees

Sep 29 - Sep 30

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

17. Howard Johnson by Wyndham Lenox

Lenox

COLLEEN

￥12,425

￥13,879 total

includes taxes & fees

Sep 29 - Sep 30

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

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

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.

18. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Jared

￥18,401

￥23,629 total

includes taxes & fees

Oct 18 - Oct 19

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 small cabin with two Adirondack chairs in a grassy field, surrounded by trees and a mountain in the background.

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

19. Granville House

Housatonic

Nicole

￥35,231

￥39,353 total

includes taxes & fees

Sep 29 - Sep 30

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

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

20. The Brooks Motel

Hillsdale

Nelson

￥21,326

￥23,885 total

includes taxes & fees

Oct 6 - Oct 7

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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

10/10 Excellent

"Amazing!"

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"The room was very nice. Updated and clean Miniature golf fun . A lot of things to do. The staff pleasant and helpful. Would stay again"

Hampton Inn & Suites Berkshires-Lenox

8/10 Good

"Breakfast was great"

Quality Inn Lee - Lenox South

8/10 Good

"Typical every day hotel, but clean and comfortable bed. Water pressure could be better."

The Yankee Inn

10/10 Excellent

"There was a nice set up for the complimentary breakfast."

Quality Inn Great Barrington

10/10 Excellent

"Front desk guy was great very helpful.. rooms were clean,good location"

The Red Lion Inn

10/10 Excellent

"Another unforgettable experience at the Red Lion. My family has been coming up for 50 years, we’re happy to continue the tradition. Wether Fall, Spring, Summer or Winter, the 4 seasons at the Red Lion are always a favorite!"

Wilder House Berkshires

10/10 Excellent

"Wonderful stay! Intend to be back here."

The Whitlock

10/10 Excellent

"The hotel staff were very friendly and helpful. There is ample parking and the location in town is great for walking to shops and restaurants. This is a very nice property."

More cheap stays in Sheffield

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

￥12,425

￥13,879 total

Sep 29 - Sep 30

includes taxes & fees

7.6/10 Good! (917 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

￥15,909

￥17,771 total

Oct 18 - Oct 19

includes taxes & fees

8.6/10 Excellent! (1,003 reviews)

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

1055 South Street Pittsfield MA

￥16,200

￥18,096 total

Oct 29 - Oct 30

includes taxes & fees

The Yankee Inn

461 Pittsfield Rd Lenox MA

￥16,986

￥18,974 total

Oct 27 - Oct 28

includes taxes & fees

9.2/10 Wonderful! (1,014 reviews)

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

￥17,246

￥19,263 total

Oct 19 - Oct 20

includes taxes & fees

8.4/10 Very Good! (1,008 reviews)

The Whitlock

16 Church St Lenox MA

￥21,796

￥24,346 total

Sep 29 - Sep 30

includes taxes & fees

8.4/10 Very Good! (387 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 33 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, Ashley House, and Mount Everett State Reservation. 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 ￥10,627

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

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. Locust Tree Bed and Breakfast LLC

8. Little Cat Lodge

9. Blackberry River Inn

10. The Little Lion

11. Econo Lodge Lee - Great Barrington

12. East Rock Inn

13. Pleasant Valley Motel West Stockbridge

14. Quality Inn Lee - Lenox South

15. the Alander

16. Berkshire Travel Lodge

17. Howard Johnson by Wyndham Lenox

18. Holiday Inn Club Vacations Oak 'n Spruce Resort

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 Club Vacations Oak 'n Spruce Resort

Hampton Inn & Suites Berkshires-Lenox

Quality Inn Lee - Lenox South

The Yankee Inn

Quality Inn Great Barrington

The Red Lion Inn

Wilder House Berkshires

The Whitlock

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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