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

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Our top choices for Sheffield hotels

Interior detail
A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.
A sign for 'Wilder House' with a maple leaf logo, established in 2023, and a date of 2023.
A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.

1. Wilder House Berkshires

Wilder House Berkshires
Sheffield
United States
Mark
￥32,578
￥36,390 total
includes taxes & fees
Oct 29 - Oct 30
Wilder House Berkshires
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 room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.
A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

2. Quality Inn Great Barrington

Quality Inn Great Barrington
Great Barrington
United States
Joan
￥12,049
￥13,458 total
includes taxes & fees
Nov 1 - Nov 2
Quality Inn Great Barrington
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
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.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
United States
Bruce
￥22,675
￥25,327 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 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

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
United States
Maria Dulce
￥14,996
￥16,751 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.
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.
A row of white plastic chairs on a covered outdoor area with a white building in the background.

5. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
United States
Victor
￥9,447
￥10,552 total
includes taxes & fees
Nov 1 - Nov 2
Monument Mountain Motel
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.
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

East Rock Inn
Great Barrington
United States
ERIK
￥23,037
￥25,732 total
includes taxes & fees
Nov 2 - Nov 3
East Rock Inn
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 spacious living room with a fireplace, patterned armchairs, and a staircase leading to an upper level.
An outdoor patio with wooden tables and chairs, surrounded by greenery.

7. Gedney Farm

Gedney Farm
Great Barrington
United States
Terri
￥26,425
￥28,988 total
includes taxes & fees
Nov 3 - Nov 4
Gedney Farm
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 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 poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

8. Little Cat Lodge

Little Cat Lodge
Copake Falls
United States
Kees
￥22,088
￥24,737 total
includes taxes & fees
Nov 5 - Nov 6
Little Cat Lodge
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 staircase leading to a deck, surrounded by trees and a gravel path.

9. Prospect Berkshires

Prospect Berkshires
Egremont
United States
Conor
￥49,012
￥60,036 total
includes taxes & fees
Nov 2 - Nov 3
Prospect Berkshires
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 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.

10. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
Great Barrington
United States
Mark
￥12,470
￥13,929 total
includes taxes & fees
Oct 18 - Oct 19
Travelodge by Wyndham Great Barrington Berkshires
A bedroom with a large bed, a chair, and a window with curtains.
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.
A dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.

11. The White Hart

The White Hart
Salisbury
United States
William
￥71,104
￥81,770 total
includes taxes & fees
Oct 7 - Oct 8
The White Hart
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 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.

12. Blackberry River Inn

Blackberry River Inn
Norfolk
United States
diane
￥20,362
￥23,416 total
includes taxes & fees
Nov 4 - Nov 5
Blackberry River Inn
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.

13. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
Catherine
￥45,777
￥55,239 total
includes taxes & fees
Nov 1 - Nov 2
The Old Inn On The Green
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 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.

14. The Little Lion

The Little Lion
Great Barrington
United States
Lidia
￥16,337
￥18,249 total
includes taxes & fees
Oct 18 - Oct 19
The Little Lion
A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.
A dog standing at a door entrance with a wooden floor and a mat with paw prints.
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.

15. the Alander

the Alander
Copake
United States
Thomas
￥22,809
￥25,546 total
includes taxes & fees
Oct 12 - Oct 13
the Alander
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 bedroom with a wooden bed, two bedside tables, a window with curtains, and a radiator.

16. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
East Canaan
United States
Daniel
￥16,574
￥19,060 total
includes taxes & fees
Oct 6 - Oct 7
Locust Tree Bed and Breakfast LLC
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 bar with wooden floors and shelves filled with bottles.
A covered porch with wicker furniture and hanging flower baskets.

17. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
￥24,864
￥35,615 total
includes taxes & fees
Nov 3 - Nov 4
The Red Lion Inn
A reception area with a fireplace, seating, and a doormat with the logo "Quality".
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.
A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

18. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
United States
Christine
￥15,967
￥17,835 total
includes taxes & fees
Oct 26 - Oct 27
Quality Inn Lee - Lenox South
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

Granville House
Housatonic
United States
Nicole
￥35,358
￥39,495 total
includes taxes & fees
Oct 7 - Oct 8
Granville House
A building with a porch and multiple windows, surrounded by purple flowers.
A café with a display case, a frozen food section, and a marketplace sign.
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.

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
United States
Jared
￥17,616
￥22,763 total
includes taxes & fees
Oct 8 - Oct 9
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
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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.
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.
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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
A covered wooden structure with a sloped roof, surrounded by greenery and trees.

Top Sheffield Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"Nice unit. Fit our needs perfectly. Convenient to a large variety of different activities."
Hugh 2-night trip
Posted less than an hour ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
Prospect Berkshires

Prospect Berkshires

10/10 Excellent
"Absolutely spectacular resort! Could not have enjoyed more."
Alexis 1-night trip
Posted 14 hours ago
Prospect Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The cleaning staff were friendly and helpful!"
Mayra 2-night trip
Posted 14 hours ago
Quality Inn Great Barrington
Berkshires Untold

Berkshires Untold

8/10 Good
"Fantastic location, and friendly staff. The rooms were comfortable."
David 1-night trip
Posted 15 hours ago
Berkshires Untold
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"Room was clean, bed was comfortable, breakfast was good, centrally located for our days events!"
Chuck 1-night trip
Posted 2 days ago
Quality Inn Lee - Lenox South
Interlaken Inn & Resort

Interlaken Inn & Resort

10/10 Excellent
"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."
Suzanne 5-night trip
Posted 4 days ago
Interlaken Inn & Resort
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

10/10 Excellent
"I was only there to sleep for a few hours"
Thomas 1-night trip
Posted 6 days ago
Courtyard by Marriott Lenox Berkshires

More cheap stays in Sheffield

Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
￥12,049
￥13,458 total
Nov 1 - Nov 2
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
Quality Inn Great Barrington
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
￥12,470
￥13,929 total
Oct 6 - Oct 7
includes taxes & fees
Howard Johnson by Wyndham Lenox
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA
￥15,967
￥17,835 total
Oct 26 - Oct 27
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Quality Inn Lee - Lenox South
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

1055 South Street Pittsfield MA
￥16,259
￥18,161 total
Nov 2 - Nov 3
includes taxes & fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
￥16,732
￥18,690 total
Nov 1 - Nov 2
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
The Yankee Inn
The Whitlock

The Whitlock

16 Church St Lenox MA
￥20,931
￥23,380 total
Nov 2 - Nov 3
includes taxes & fees
The Whitlock

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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