Top 10 Hotels in Sheffield, MA from ￥10,555 - Competitive Prices

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Sheffield

Pool

Hot tub

Family friendly

Waterpark

Pet friendly

Apartment

Condo

Cottage

Cabin

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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

￥32,231

￥36,001 total

includes taxes & fees

Nov 2 - Nov 3

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

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'.

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

2. Quality Inn Great Barrington

Great Barrington

Joan

￥11,951

￥13,349 total

includes taxes & fees

Nov 1 - Nov 2

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

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

￥22,682

￥25,336 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

￥13,140

￥14,677 total

includes taxes & fees

Nov 10 - Nov 11

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

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

￥9,450

￥10,555 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 grassy outdoor area with four blue Adirondack chairs arranged in a circle.

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

￥19,965

￥22,301 total

includes taxes & fees

Nov 10 - Nov 11

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

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

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

A spacious living room with a fireplace, patterned armchairs, and a staircase leading to an upper level.

7. Gedney Farm

Great Barrington

Terri

￥26,501

￥29,072 total

includes taxes & fees

Nov 3 - Nov 4

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

A wooden wall with a white pendant light fixture.

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.

8. Prospect Berkshires

Egremont

Conor

￥44,881

￥55,437 total

includes taxes & fees

Nov 10 - Nov 11

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

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

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.

9. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

￥12,474

￥13,933 total

includes taxes & fees

Oct 12 - Oct 13

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

A house with a stone patio and wooden stools.

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.

10. Little Cat Lodge

Copake Falls

Kees

￥24,016

￥26,899 total

includes taxes & fees

Nov 2 - Nov 3

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

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

11. Blackberry River Inn

Norfolk

Donna

￥30,001

￥34,501 total

includes taxes & fees

Oct 13 - Oct 14

A large house with a balcony and a grassy yard.

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

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

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

12. The Little Lion

Great Barrington

Lidia

￥16,343

￥18,256 total

includes taxes & fees

Oct 18 - Oct 19

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

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

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.

13. The Old Inn On The Green

Great Barrington

Catherine

￥45,791

￥55,256 total

includes taxes & fees

Nov 2 - Nov 3

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 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.

14. The White Hart

Salisbury

William

￥142,954

￥164,397 total

includes taxes & fees

Oct 24 - Oct 25

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 covered porch with white railings and rocking chairs.

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

￥16,580

￥19,067 total

includes taxes & fees

Oct 11 - Oct 12

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

16. the Alander

Copake

Thomas

￥26,843

￥30,062 total

includes taxes & fees

Oct 12 - Oct 13

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 covered porch with wicker furniture and hanging flower baskets.

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

17. The Red Lion Inn

Stockbridge

Stephan

￥24,873

￥35,628 total

includes taxes & fees

Nov 3 - Nov 4

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

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

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

South Lee

Jared

￥18,474

￥23,722 total

includes taxes & fees

Oct 12 - Oct 13

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.

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

19. Quality Inn Lee - Lenox South

Lee

Christine

￥14,629

￥16,341 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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.

20. Granville House

Housatonic

Marcia

￥40,107

￥44,800 total

includes taxes & fees

Oct 12 - Oct 13

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

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

Top Sheffield Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"Service is excellent and the location is so convenient. Rooms have amazing amenities!"

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

10/10 Excellent

"The property was very well maintained and the room was very clean. Check in was quick and easy. The included breakfast was satisfying. Would stay here again."

The Yankee Inn

10/10 Excellent

"Although it's an older hotel, it's well maintained.Clean and updated also very friendly staff."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"no comment"

Quality Inn Lee - Lenox South

10/10 Excellent

"My wife and I were touring the Berkshires near the end of a long road trip. We’re so glad we chose this Quality Inn in Lee for our stay! Staff in the afternoon/evening, at breakfast, and at the morning desk were all professional, friendly, and helpful. Our room was very clean and comfortable, and the amenities worked well. The continental breakfast included not only stations for waffles and toast, it also included tasty Jimmy Dean breakfast sandwiches to microwave. Coffee and tea and hot chocolate were available 24/7. Art related to nature and the Berkshires was on the walls. A highly recommended property!"

The Cornell Inn, Lenox & The Berkshires

8/10 Good

"Nice Inn/B&B in Lenox MA, about a mile from downtown."

the Alander

10/10 Excellent

"I wanted to sit by the firepit with my delicious Lobster Bisque from their restaurant and Reid jumped in right away and offered to start up the Firepit for me. I love the attention to the guest. It's the little things. Thank you for a good night's rest."

The Red Lion Inn

8/10 Good

"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"

Quality Inn Great Barrington

8/10 Good

"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."

More cheap stays in Sheffield

Quality Inn Great Barrington

372 Main Street Great Barrington MA

￥11,951

￥13,349 total

Nov 1 - Nov 2

includes taxes & fees

8.6/10 Excellent! (1,003 reviews)

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

￥12,474

￥13,933 total

Oct 18 - Oct 19

includes taxes & fees

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

￥14,629

￥16,341 total

Nov 1 - Nov 2

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

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

1055 South Street Pittsfield MA

￥15,673

￥17,506 total

Nov 9 - Nov 10

includes taxes & fees

9.2/10 Wonderful! (232 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

￥16,737

￥18,695 total

Nov 1 - Nov 2

includes taxes & fees

9.2/10 Wonderful! (1,001 reviews)

The Whitlock

16 Church St Lenox MA

￥23,113

￥25,817 total

Nov 3 - Nov 4

includes taxes & fees

8.4/10 Very Good! (395 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.

Explore a world of travel with Expedia

Richmond Vacations

Peru Vacation Rentals

Book Hotels in Sheffield on Expedia.com

Find hotels in Sheffield, MA from ￥10,555

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. Gedney Farm

8. Prospect Berkshires

9. Travelodge by Wyndham Great Barrington Berkshires

10. Little Cat Lodge

11. Blackberry River Inn

12. The Little Lion

13. The Old Inn On The Green

14. The White Hart

15. Locust Tree Bed and Breakfast LLC

16. the Alander

17. The Red Lion Inn

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

19. Quality Inn Lee - Lenox South

20. Granville House

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

Berkshire Mountain Lodge

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

The Yankee Inn

Holiday Inn Club Vacations Oak 'n Spruce Resort

Quality Inn Lee - Lenox South

The Cornell Inn, Lenox & The Berkshires

the Alander

The Red Lion Inn

Quality Inn Great Barrington

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

Explore a world of travel with Expedia

Go further with the Expedia app