Hotels in Sheffield

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Where to stay in Sheffield?

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

A spacious lobby with a fireplace, seating area, and a bar.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

1. Berkshire Mountain Lodge

Pittsfield

$93

$126 total

includes taxes & fees

Oct 1 - Oct 2

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

A cozy library with bookshelves, a fireplace, and comfortable seating.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

2. Berkshires Untold

Lenox

$145

$162 total

includes taxes & fees

Sep 28 - Sep 29

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 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.

3. Little Cat Lodge

Copake Falls

$199

$223 total

includes taxes & fees

Sep 13 - Sep 14

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

4. The Yankee Inn

Lenox

$116

$130 total

includes taxes & fees

Sep 22 - Sep 23

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

A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.

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.

5. Prospect Berkshires

Egremont

$365

$441 total

includes taxes & fees

Sep 17 - Sep 18

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

A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.

6. Quality Inn Great Barrington

Great Barrington

$104

$116 total

includes taxes & fees

Sep 13 - Sep 14

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A backyard with a swimming pool, lounge chairs, and a hot tub.

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.

7. The Red Lion Inn

Stockbridge

$162

$231 total

includes taxes & fees

Sep 30 - Oct 1

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

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.

8. Wilder House Berkshires

Sheffield

$195

$218 total

includes taxes & fees

Sep 14 - Sep 15

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

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

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.

9. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

$117

$150 total

includes taxes & fees

Sep 13 - Sep 14

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.

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

Great Barrington

$124

$139 total

includes taxes & fees

Sep 15 - Sep 16

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.

11. the Alander

Copake

$145

$162 total

includes taxes & fees

Sep 14 - Sep 15

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.

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

Great Barrington

$186

$208 total

includes taxes & fees

Sep 14 - Sep 15

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A lakeside dock with kayaks and a covered boat ramp.

A lodge with a large building and a dock by a lake, surrounded by forest.

A lakeside lodge with a dock, fishing rods, and outdoor seating.

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

Lee

$128

$142 total

includes taxes & fees

Sep 30 - Oct 1

A large house with a balcony and a grassy yard.

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

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.

14. The Little Lion

Great Barrington

$125

$140 total

includes taxes & fees

Sep 13 - Sep 14

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.

15. Monument Mountain Motel

Great Barrington

$95

$106 total

includes taxes & fees

Sep 13 - Sep 14

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

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

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.

16. Blackberry River Inn

Norfolk

$170

$196 total

includes taxes & fees

Sep 13 - Sep 14

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

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.

A covered porch with white railings and rocking chairs.

17. Locust Tree Bed and Breakfast LLC

East Canaan

$105

$121 total

includes taxes & fees

Sep 11 - Sep 12

A spacious interior with a high ceiling, exposed brick walls, large windows, and modern furniture.

A modern bar area with a long counter, multiple stools, and a seating area with a large potted plant and a table with a vase.

A modern interior with a brick fireplace, comfortable seating, and large windows offering views of the outdoors.

18. voco James Newbury Hudson Valley by IHG

Coxsackie

$161

$180 total

includes taxes & fees

Sep 13 - Sep 14

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.

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

19. Gedney Farm

Great Barrington

$243

$267 total

includes taxes & fees

Sep 11 - Sep 12

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.

20. East Rock Inn

Great Barrington

$155

$173 total

includes taxes & fees

Sep 13 - Sep 14

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Go beyond your typical stay in Sheffield

Pet friendly

Pool

Hot tub

Cottage

Family friendly

Our prices for hotels in Sheffield are cheapest in April

Top landmarks in Sheffield

Ashley House

If you're planning a bit of sightseeing during your trip, head to Ashley House— just one of the landmarks located 3.5 mi (5.6 km) from central Sheffield.

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Thom Reed UFO Monument Park

8.0/10 (1 review)

Thom Reed UFO Monument Park is 1 mi (1.5 km) from central Sheffield, why not stop by during your stay. Want to stretch your legs some more? Head to Umpachene Falls Park, located nearby.

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Bartholomews Cobble

Bartholomews Cobble is 4.2 mi (6.8 km) from central Sheffield, why not stop by during your stay. Want to stretch your legs some more? Head to Umpachene Falls Park and Eddy Field, both nearby.

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Bartholomew's Cobble

10.0/10 (1 review)

Bartholomew's Cobble is 3.8 mi (6.1 km) from central Sheffield, why not stop by during your stay.

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Drury Preserve

Drury Preserve is 2.5 mi (3.9 km) from central Sheffield, why not stop by during your stay.

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Lime Kiln Farm Wildlife Sanctuary

Lime Kiln Farm Wildlife Sanctuary is 1.7 mi (2.7 km) from central Sheffield, why not stop by during your stay.

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Learn more about Sheffield

Sheffield is well-known for its attractions such as Housatonic River and Three Mile Pond Wildlife Management Area.

See all hotels in Sheffield

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

Check out reviews of Sheffield hotels guests love

Berkshires Untold

10/10 Excellent

"beautiful place, great staff, would love to go back!"

Berkshire Mountain Lodge

10/10 Excellent

"Very nice hotel. I would definitely stay here again."

Little Cat Lodge

10/10 Excellent

"Beautiful and peaceful little lodge with easy access to all the wonderful things in the area (Catamount, Lakes etc..). Pool is very tranquil and each room has Mountain views. The lodge is artfully designed as well, providing a luxury feeling. I only wish 1) the indoor common area was open for guests at any time (but I assume this is a cost/staff issue) 2) there as espessso / coffee/ tea available for guests at a wider ranger of hours (only available at continental breakfast or kureg in room). But these would only be added luxuries and did not materially detract from absolutely delightful stay!!"

The Yankee Inn

10/10 Excellent

"Excellent in every way. Service, staff, amenities. Everything was perfect."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Generous front desk (forgot toothbrush & comb, they gave us both free of charge). Great complimentary breakfast & tea/coffee machine. Great WiFi. Beautiful view & kayaking was so fun. We had a wonderful stay!"

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."

Wilder House Berkshires

10/10 Excellent

"Just a beautiful home with clean, comfortable rooms and an amazing Innkeeper. Breakfasts are elegant and delicious. We stayed here in 2025 and returned in 2026 for Labor Day weekend. Will hopefully repeat in 2027."

Quality Inn Lee - Lenox South

8/10 Good

"Very clean property with kind staff. Nice room, decent complimentary coffee, breakfast offerings not for me."

Hideaway Inn Lenox

10/10 Excellent

"We reserved this Inn because of its close proximity to Tanglewood. Easy check-in and check-out. The queen bed was super comfortable. Room clean. It was nice to have coffee available 24/7. Would stay here again!"

Frequently asked questions

What accommodations do travelers recommend in Sheffield?

Guests like Wilder House Berkshires, Quality Inn Great Barrington and Little Cat Lodge.

Can I book a refundable accommodation in Sheffield?

If you want the flexibility to change your travel plans to Sheffield, most accommodations offer refundable* bookable rates. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Sheffield if I want a vacation rental instead of a traditional hotel?

If you want to find a good alternative to a hotel, browse our selection of 23 vacation homes.

What will the weather in Sheffield be like during my vacation?

The warmest months in Sheffield are usually July and August with an average temp of 66°F. January and February are the chilliest months when the average temp is 28°F. The rainiest months are July and August.

Why should I book my Sheffield accommodation with Hotels.com?

There are plenty of reasons to book your Sheffield travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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More ways to book

Book Hotels in Sheffield on Hotels.com

Hotels in Sheffield

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Where to stay in Sheffield?

1. Berkshire Mountain Lodge

2. Berkshires Untold

3. Little Cat Lodge

4. The Yankee Inn

5. Prospect Berkshires

6. Quality Inn Great Barrington

7. The Red Lion Inn

8. Wilder House Berkshires

9. Holiday Inn Club Vacations Oak 'n Spruce Resort

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

11. the Alander

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

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

14. The Little Lion

15. Monument Mountain Motel

16. Blackberry River Inn

17. Locust Tree Bed and Breakfast LLC

18. voco James Newbury Hudson Valley by IHG

19. Gedney Farm

20. East Rock Inn

Go beyond your typical stay in Sheffield

Price trends for hotels in Sheffield

Typical weather for Sheffield

Top landmarks in Sheffield

Ashley House

Thom Reed UFO Monument Park

Bartholomews Cobble

Bartholomew's Cobble

Drury Preserve

Lime Kiln Farm Wildlife Sanctuary

Learn more about Sheffield

Check out reviews of Sheffield hotels guests love

Berkshires Untold

Berkshire Mountain Lodge

Little Cat Lodge

The Yankee Inn

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Holiday Inn Club Vacations Oak 'n Spruce Resort

Wilder House Berkshires

Quality Inn Lee - Lenox South

Hideaway Inn Lenox

Frequently asked questions

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