𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Sheffield (2026)

A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

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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

Liliana

₹16,453

₹18,377 total

includes taxes & fees

2 Nov - 3 Nov

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 wooden desk, a television, a mirror, and a bathroom visible through an open door.

2. Quality Inn Great Barrington

Downtown Great Barrington

Scott Patterson

₹7,295

₹8,149 total

includes taxes & fees

15 Nov - 16 Nov

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

Great Barrington

₹13,622

₹15,216 total

includes taxes & fees

3 Nov - 4 Nov

A modern hotel lobby with seating areas, tables, and a reception desk.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A kitchenette with a microwave, coffee maker, and coffee cups.

A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

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

Great Barrington

Cynthia

₹8,534

₹9,533 total

includes taxes & fees

12 Nov - 13 Nov

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.

5. East Rock Inn

Great Barrington

Sharon

₹11,878

₹13,268 total

includes taxes & fees

24 Nov - 25 Nov

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 motel rooms with red doors, a covered walkway, and a view of mountains in the background.

6. Monument Mountain Motel

Great Barrington

Andrea

₹5,682

₹6,347 total

includes taxes & fees

1 Nov - 2 Nov

A wooden boat on calm water with a house in the background.

A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

A wooden deck with a dog silhouette against a backdrop of autumn foliage.

A wooden table with a green chair and a yellow vase with flowers.

7. Prospect Berkshires

Egremont

Conor

₹23,417

₹29,338 total

includes taxes & fees

9 Nov - 10 Nov

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

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.

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

8. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Ramakrishnan

₹7,491

₹8,368 total

includes taxes & fees

2 Nov - 3 Nov

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

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.

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

9. Blackberry River Inn

Norfolk

Melanie

₹16,756

₹19,269 total

includes taxes & fees

25 Oct - 26 Oct

A house with a stone patio and wooden stools.

A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

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

10. Little Cat Lodge

Copake Falls

Stacy

₹13,574

₹15,203 total

includes taxes & fees

24 Nov - 25 Nov

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

A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

11. The Old Inn On The Green

Great Barrington

mary ellen

₹27,500

₹33,183 total

includes taxes & fees

1 Nov - 2 Nov

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 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.

12. The White Hart

Salisbury

William

₹28,312

₹32,559 total

includes taxes & fees

22 Nov - 23 Nov

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

13. The Little Lion

Great Barrington

David

₹9,815

₹10,963 total

includes taxes & fees

26 Oct - 27 Oct

A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

A bar area with a green counter, two pendant lights, and shelves stocked with 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 dining table set with plates of food, wine glasses, and bottles, with a chandelier above and shelves above holding glasses and bottles.

14. the Alander

Copake

Luis

₹15,172

₹16,993 total

includes taxes & fees

31 Oct - 1 Nov

A dining area with a round table and four chairs, a radiator, and a window with a view of greenery.

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.

A pool table in a room with a patterned rug, a shelf with decorative items, and a window with a view of greenery.

15. Granville House

Housatonic

Cynthia

₹24,115

₹26,937 total

includes taxes & fees

25 Oct - 26 Oct

A straw hat, sunglasses, and two drinks on a striped towel by a body of water.

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.

16. The Red Lion Inn

Stockbridge

Mallory

₹14,955

₹21,422 total

includes taxes & fees

4 Nov - 5 Nov

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.

A bedroom with a wooden bed, two bedside tables, a window with curtains, and a radiator.

17. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

₹9,957

₹11,450 total

includes taxes & fees

2 Nov - 3 Nov

A multi-story building with a balcony, a pond with rocks, and a tree.

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.

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

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

South Lee

Michael

₹11,095

₹14,247 total

includes taxes & fees

26 Oct - 27 Oct

A modern bedroom with a large bed, two bedside tables, and a textured wall behind the bed.

A living room with a sofa, a coffee table, a fireplace, and a ceiling fan.

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.

19. The Brooks Motel

Hillsdale

Nelson

₹13,843

₹15,504 total

includes taxes & fees

25 Oct - 26 Oct

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.

20. Quality Inn Lee - Lenox South

Lee

James

₹8,796

₹9,826 total

includes taxes & fees

15 Nov - 16 Nov

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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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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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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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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.

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Top Sheffield Hotel Reviews

Quality Inn Great Barrington

10/10 Excellent

"The hotel was clean and pleasant. Staff members were courteous and helpful! Very satisfied with our stay and will consider a future stay here!"

Berkshire Mountain Lodge

10/10 Excellent

"Very nice place. Rooms are large and always clean. Pool is a nice perk"

Berkshires Untold

10/10 Excellent

"Berkshires Untold is THE PLACE to stay in Lenox. The rooms are terrific. They've been beautifully upgraded and the bathrooms are big and as nice as can be. We were concerned about the noise from the cars on Rte 7 as our room faced the street, but it was not an issue whatsoever. The breakfasts were just right. Coffee was plentiful and ready in the morning when we got up. And the owners (or managers) are suburb; they handled a problem I had with such grace and so generously I was astounded! Bottom line: next time we return for a Foliage experience, we're coming back to the Berkshires Untold!"

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"The parking lot was being resurfaced and we could not find a handicap spot near the door. It was inconvenient, and one handicap spot was filled by a car without a handicap placard."

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Wonderful staff , great location ! Fresh brownies offered at check in , specialty cocktails in the evening , lovely breakfast in the morning:)"

The Yankee Inn

10/10 Excellent

"I would prefer more flexibility making reservations. Online and by phone, I wanted two rooms for two people. I was forced to request two rooms for THREE people to work around the algorithm that allowed only one room for two people. Also I was forced to accept two rooms in the same price range, when I wanted one premium king, not two. I left another hotel due to their inflexibility, and I will choose one with a personal approach next time."

Quality Inn Lee - Lenox South

10/10 Excellent

"A"

The Red Lion Inn

8/10 Good

"Absolutely great location! An older property- the lobby and hallways seemed dark and aging (yes it’s historic). Our room was surprisingly cheerful! I’d stay here again!!"

The Whitlock

10/10 Excellent

"Nice location."