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
￥31,391
￥35,063 total
includes taxes & fees
Oct 25 - Oct 26
Wilder House Berkshires
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.
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.
A Quality Inn sign, a brick building, and a parking lot with cars.

2. Quality Inn Great Barrington

Quality Inn Great Barrington
Downtown Great Barrington
United States
Joan
￥12,286
￥13,723 total
includes taxes & fees
Nov 10 - Nov 11
Quality Inn Great Barrington
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
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.

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
Canada
Kelly
￥22,741
￥25,403 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 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 hotel room with two beds, a desk, a TV, and a window with curtains.

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
￥13,140
￥14,677 total
includes taxes & fees
Nov 10 - Nov 11
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 motel with a parking lot and several cars parked.
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.

5. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
United States
Andrea
￥9,475
￥10,583 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 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.
A hotel room with two beds, a desk, a TV, and a window with curtains.

6. East Rock Inn

East Rock Inn
Great Barrington
United States
ERIK
￥19,965
￥22,301 total
includes taxes & fees
Nov 12 - Nov 13
East Rock Inn
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.
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.
A motel with a two-story structure, multiple rooms with red doors, and a central staircase.

7. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
Great Barrington
United States
Mark
￥12,506
￥13,970 total
includes taxes & fees
Oct 13 - Oct 14
Travelodge by Wyndham Great Barrington Berkshires
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 bed, a chair, and a table by a large window overlooking a lake.

8. Prospect Berkshires

Prospect Berkshires
Egremont
United States
Conor
￥43,285
￥53,656 total
includes taxes & fees
Nov 4 - Nov 5
Prospect Berkshires
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
A poolside area with lounge chairs and blue umbrellas, surrounded by 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 house with a stone patio and wooden stools.

9. Little Cat Lodge

Little Cat Lodge
Copake Falls
United States
Kees
￥21,430
￥24,001 total
includes taxes & fees
Nov 11 - Nov 12
Little Cat Lodge
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.

10. Blackberry River Inn

Blackberry River Inn
Norfolk
United States
Donna
￥30,079
￥34,591 total
includes taxes & fees
Oct 13 - Oct 14
Blackberry River Inn
A large house with a balcony and a grassy yard.
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.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

11. The Little Lion

The Little Lion
Great Barrington
United States
Lidia
￥16,385
￥18,302 total
includes taxes & fees
Oct 18 - Oct 19
The Little Lion
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 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.

12. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
Catherine
￥45,910
￥55,399 total
includes taxes & fees
Nov 1 - Nov 2
The Old Inn On The Green
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 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.

13. the Alander

the Alander
Copake
United States
Thomas
￥26,913
￥30,144 total
includes taxes & fees
Oct 13 - Oct 14
the Alander
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 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.

14. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
East Canaan
United States
Daniel
￥16,623
￥19,116 total
includes taxes & fees
Oct 13 - Oct 14
Locust Tree Bed and Breakfast LLC
A bedroom with a large bed, a chair, and a window with curtains.
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 covered porch with a dining area, a sofa, and decorative wall art.
A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

15. The White Hart

The White Hart
Salisbury
United States
William
￥142,954
￥164,397 total
includes taxes & fees
Oct 24 - Oct 25
The White Hart
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 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.

16. 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
￥18,522
￥23,785 total
includes taxes & fees
Oct 14 - Oct 15
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A covered porch with wicker furniture and hanging flower baskets.
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.

17. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
￥24,936
￥35,718 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 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.

18. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
United States
Christine
￥14,667
￥16,383 total
includes taxes & fees
Nov 1 - Nov 2
Quality Inn Lee - Lenox South
A dining table with pastries, a coffee pot, and a vase of sunflowers.
A large, two-story white building with a symmetrical facade, columns, and a central entrance.
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.

19. Granville House

Granville House
Housatonic
United States
Cynthia
￥40,211
￥44,916 total
includes taxes & fees
Oct 18 - Oct 19
Granville House
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A dining area with large windows, wooden furniture, and a view of a lake.
A lodge with a large building and a dock by a lake, surrounded by forest.

20. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Bob
￥18,166
￥20,292 total
includes taxes & fees
Nov 8 - Nov 9
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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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.
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.
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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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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.
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
A covered wooden structure with a sloped roof, surrounded by greenery and trees.

Top Sheffield Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"It was good"
Vishva 1-night trip
Posted 5 hours ago
Hampton Inn & Suites Berkshires-Lenox
Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Comfortable and cozy suite, large living room/dining area, kitchen and large bedroom, will stay again"
Peter 1-night trip
Posted 7 hours ago
Berkshire Mountain Lodge
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"My daughter and I stayed at this Inn for a girls weekend and it was a perfect way to kick off our fall weekend. From great service to delicious breakfast everything was taken care of."
Leslie K 1-night trip
Posted 8 hours ago
The Cornell Inn, Lenox & The Berkshires
Berkshires Untold

Berkshires Untold

8/10 Good
"First this is a gorgeous property, the outdoor areas are wonderful, with comfy furniture, flowers and fire pits. The main area is an intimate restaurant and bar, with a seating area with books and plants. We enjoyed drinks and dinner there and it was excellent, particularly with the sunset and fire pit to begin our evening, Absolutely lovely! Upon checking in, we were assigned a “premium” room, which sounded great, however it turned out to be on the second floor, at the end of a very long outside corridor, parking and lobby quite distant. They have no elevator. We did lug our bags and a cooler to the room, which was lovely, but we knew we would be much more comfortable on the first floor closer to the lobby, as we are somewhat older. We asked to be moved, and we accommodated, found the room the same, but lacking the coffee service and luggage rack. We were brought a luggage rack, and complimentary coffee was available in the lobby in the morning, but it seemed odd that those would be considered premium in such a nice place. The star of the place is the beautiful outdoor space, and restaurant, we just loved that!"
William 1-night trip
Posted 9 hours ago
Berkshires Untold
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"First, this is an absolutely gorgeous place! The outside areas are beautiful with comfy furniture, flowers and fire pits. Inside is a small intimate restaurant and bar, plus sitting area. With books and plants, very nice. We had dinner there which was excellent, and loved cocktails and sunset outside by the fire pits. When we checked in, we were assigned one of their premium rooms, which sounded great. However, it was on the second floor, at the very end of a long outside corridor, accessible only by stairs near the lobby. There is no elevator. We did go to the room, lugging our bags and a cooler. Unpleasant, as we are somewhat older. We concluded that we did not want to be that far from the main area, so asked to be moved, and were accommodated. We found the new room the same, but lacking a luggage rack and a coffee service (those were only available in the premium rooms at the end of the long corridor). We were given a luggage rack, and complimentary coffee was available in the restaurant in the morning, but it seemed odd that those were considered premium in such a nice place. Otherwise we loved the hotel, room was very nice with a comfortable bed and a very updated bath with a walk in shower. The real star of the hotel is the lobby restaurant and outdoor space - that was just perfect!"
William 1-night trip
Posted 9 hours ago
Quality Inn Great Barrington
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"Good breakfast. Great location"
Martin 1-night trip
Posted 9 hours ago
Quality Inn Lee - Lenox South
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"The hotel is an older building but is clean and well maintained. The view of the lake was nice. Breakfast was just ok. Bed was very comfortable. Michelle was very helpful. My only disappointment was that the kayaks were not complimentary. It cost $30 an hour for each kayak."
Lise 2-night trip
Posted 15 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"The room was incredible. Just need to be a little friendly at the arrival."
Roberto 2-night trip
Posted 1 day ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent
"Excellent room! Clean and good breakfast!"
Kelly 1-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

More cheap stays in Sheffield

Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
￥12,286
￥13,723 total
Nov 10 - Nov 11
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Quality Inn Great Barrington
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
￥12,506
￥13,970 total
Oct 18 - Oct 19
includes taxes & fees
Howard Johnson by Wyndham Lenox
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA
￥14,667
￥16,383 total
Nov 1 - Nov 2
includes taxes & fees
8.6/10 Excellent! (1,001 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
￥15,673
￥17,506 total
Nov 9 - Nov 10
includes taxes & fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
￥16,781
￥18,744 total
Nov 1 - Nov 2
includes taxes & fees
The Yankee Inn
The Whitlock

The Whitlock

16 Church St Lenox MA
￥23,272
￥25,995 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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