Top 10 Hotels in Sheffield, MA (from $76) 2026 - Competitive Prices

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

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Our top choices for Sheffield hotels

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.

A garden with wooden Adirondack chairs and a stone pathway.

1. Berkshire Mountain Lodge

Pittsfield

Jonathan

$109 nightly

$121 total

Oct 1 - Oct 2

Total with taxes and fees

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

A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

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".

2. Berkshires Untold

Lenox

Sue

$143 nightly

$160 total

Sep 28 - Sep 29

Total with taxes and fees

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 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.

3. The Red Lion Inn

Stockbridge

Gerald

$195 nightly

$217 total

Sep 29 - Sep 30

Total with taxes and fees

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

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

4. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Diane

$135 nightly

$150 total

Sep 29 - Sep 30

Total with taxes and fees

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 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.

5. Little Cat Lodge

Copake Falls

Lindsey

$199 nightly

$223 total

Sep 27 - Sep 28

Total with taxes and fees

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

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 view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

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

6. The Yankee Inn

Lenox

Tanya

$108 nightly

$121 total

Oct 27 - Oct 28

Total with taxes and fees

A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.

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.

7. Wilder House Berkshires

Sheffield

Jeffrey

$197 nightly

$220 total

Sep 27 - Sep 28

Total with taxes and fees

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

8. Quality Inn Great Barrington

Great Barrington

Deborah

$101 nightly

$113 total

Oct 18 - Oct 19

Total with taxes and fees

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 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.

9. Prospect Berkshires

Egremont

Kellee

$395 nightly

$441 total

Sep 27 - Sep 28

Total with taxes and fees

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

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.

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

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

Lee

Howard

$138 nightly

$154 total

Sep 29 - Sep 30

Total with taxes and fees

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.

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

Great Barrington

Joan

$169 nightly

$189 total

Oct 1 - Oct 2

Total with taxes and fees

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 dining table set with plates of food, wine glasses, and bottles, with a chandelier above and shelves above holding glasses and bottles.

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

12. the Alander

Copake

Herman

$145 nightly

$162 total

Sep 30 - Oct 1

Total with taxes and fees

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.

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

Great Barrington

Maria Dulce

$119 nightly

$133 total

Oct 19 - Oct 20

Total with taxes and fees

An indoor swimming pool with a concrete floor, a large window, and a vase with flowers.

A spacious room with leather seating, large windows, and exposed brick walls.

A bar area with wooden beams, a bar counter, and stools.

A restaurant with long tables, chairs, and a brick wall.

14. Pocketbook Hotel and Bath

Hudson

Leigh

$284 nightly

$321 total

Oct 26 - Oct 27

Total with taxes and fees

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

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

15. Monument Mountain Motel

Great Barrington

Victor

$76 nightly

$85 total

Oct 25 - Oct 26

Total with taxes and fees

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 grand hallway with a chandelier, a staircase, and a table with flowers.

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

16. Blackberry River Inn

Norfolk

Olivia

$140 nightly

$161 total

Sep 30 - Oct 1

Total with taxes and fees

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 large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

A dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.

17. The White Hart

Salisbury

William

$344 nightly

$396 total

Sep 28 - Sep 29

Total with taxes and fees

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

A two-story building with a flat roof, solar panels, and a small patio area.

18. Locust Tree Bed and Breakfast LLC

East Canaan

$105 nightly

$121 total

Sep 27 - Sep 28

Total with taxes and fees

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

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.

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

19. The Old Inn On The Green

Great Barrington

Anonymous traveler

$363 nightly

$398 total

Sep 27 - Sep 28

Total with taxes and fees

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

An outdoor patio with wooden tables and chairs, surrounded by greenery.

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.

20. Gedney Farm

Great Barrington

Terri

$221 nightly

$243 total

Oct 18 - Oct 19

Total with taxes and fees

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Where to stay near Sheffield

Sheffield, MA offers a delightful blend of outdoor adventures and historical charm. Explore the scenic Sheffield districts and enjoy family-friendly activities, all within walking distance. Perfect for Berkshires vacations, this destination promises an atmosphere filled with relaxation and friendly people, making it an ideal getaway.

A building with a marquee sign reading "MAHAIWE Performing Arts Center" and a smaller sign for "Black Violin" performances.

A waterfall surrounded by autumn foliage.

A row of parked cars along a street lined with brick buildings, including a sign for 'Vault Studio' and 'Hotpoint'.

A brick building with a white door, arched windows, and a clock tower.

A frozen waterfall surrounded by snow-covered trees and rocks.

Great Barrington

Discover Great Barrington, a welcoming destination perfectly suited for nature lovers and families seeking a weekend getaway. With its beautiful landscapes, you can explore the stunning Housatonic River, take in the views at Lake Buel, or visit the serene National Shrine of the Divine Mercy. Located about 6 miles by car from Sheffield, Great Barrington offers easy access to outdoor adventures, including skiing and hiking. It's a smart choice for your stay in the Berkshires, blending relaxation with exciting activities.

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Ashley Falls

Experience the charm of Ashley Falls, a delightful hub for families and nature enthusiasts eager to enjoy outdoor adventures. Just a short drive from Sheffield, Ashley Falls offers access to a ski field, a national state park, and scenic lakes, perfect for weekend getaways. With a mix of attractions like the Ashley House museum and the serene Ashley Falls Woods nature reserve, this area caters to those looking for both relaxation and excitement. Choosing Ashley Falls for your stay ensures a memorable retreat in the heart of nature.

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A waterfall cascading over rocks in a forested area.

A rocky stream with a waterfall surrounded by autumn-colored trees.

Mount Washington

If you are a family or nature enthusiast, look no further than Mount Washington, a charming village known for its breathtaking outdoor scenery and adventure opportunities. With attractions like Taconic State Park and the Mount Washington State Forest, visitors can immerse themselves in nature while enjoying activities such as skiing in nearby resorts. Located about 5 miles from Sheffield, Mount Washington is an excellent choice for your stay, offering a peaceful retreat with easy access to memorable experiences.

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A white building with a sign that reads "Egnemont Free Library Archives."

South Egremont

South Egremont stands out as a prime spot for travelers seeking a family-friendly weekend getaway immersed in nature. With its close proximity to attractions like the breathtaking Bash Bish Falls State Park, the serene Housatonic River, and the spiritual National Shrine of the Divine Mercy, visitors can enjoy a variety of outdoor activities year-round. Located about 5 miles by car from Sheffield, South Egremont is a smart choice for those looking to explore the beauty of the Berkshires while enjoying a peaceful retreat.

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Mill River

Travelers seeking a weekend getaway or a family-friendly vacation will find Mill River to be the ideal base for their adventures, featuring stunning natural landscapes like the nearby Questing forest and Lake Buel. With opportunities for skiing, music concerts, and exploring the beautiful Umpachene Falls Park, Mill River offers a delightful mix of activities year-round, especially during the peak months of July to August and October. Located about 5 miles by car from Sheffield, Mill River is a smart choice for a memorable stay.

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Stay near popular attractions in and around Sheffield

Sheffield invites adventure seekers to explore its stunning landscapes, where outdoor enthusiasts can enjoy skiing, hiking, and serene lakeside retreats. Immerse yourself in nature at nearby parks and reserves, offering eco-friendly experiences that promise unforgettable memories of your outdoor getaway.

Housatonic River

9.0/10 (28 reviews)

Highly recommended for outdoor enthusiasts, the Housatonic River offers stunning scenery and a tranquil atmosphere perfect for relaxation and exploration. Located about 6 miles by car from Sheffield, it's an easy trip for visitors looking to enjoy nature. Staying nearby allows you to fully embrace the river's serene vibes.

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Ashley House

Experience the best of cultural exploration at Ashley House, a museum located in Sheffield, Massachusetts. This attraction offers insight into local history and heritage, showcasing unique exhibits and vibrant cultural vibes. Nestled within Sheffield, it’s a convenient spot to immerse yourself in the area’s charm and history.

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Taconic State Park

9.8/10 (11 reviews)

Often cited as a favorite among outdoor enthusiasts, Taconic State Park offers stunning scenery and a wealth of adventures to explore. Located about 8 miles from Sheffield, this park is perfect for a day trip, providing easy access to nature's beauty and outdoor activities. Staying nearby enhances your experience of this natural gem.

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Questing

No trip is complete without a visit to Questing, a haven for outdoor adventurers seeking the thrill of nature. This lush forest offers a unique experience with its serene trails and vibrant wildlife. Located about 5 miles from Sheffield, it's a convenient spot for those looking to immerse themselves in the beauty of Massachusetts.

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W.E.B. Du Bois Boyhood Homesite

8.8/10 (29 reviews)

An essential stop for history buffs, the W.E.B. Du Bois Boyhood Homesite offers a glimpse into the early life of the renowned civil rights leader. Located about 5 miles from Sheffield, this historic site embodies rich cultural vibes and is a meaningful exploration of African American heritage. Staying nearby provides easy access to this significant landmark.

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Lake Buel

8.8/10 (23 reviews)

A fascinating mix of romance and outdoor beauty, Lake Buel offers visitors a serene escape with picturesque scenery and beach vibes. Located about 6 miles by car from Sheffield, this tranquil lake is perfect for a relaxing day trip, making it an ideal spot for those looking to unwind in nature.

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Umpachene Falls Park

10.0/10 (1 review)

Perfectly suited for outdoor lovers and adventure seekers, Umpachene Falls Park features a stunning waterfall that creates a romantic atmosphere. Located about 4 miles from Sheffield, this scenic destination offers a refreshing escape into nature, making it an ideal spot to unwind after exploring the charming nearby town.

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Dry Hill

7.4/10 (8 reviews)

A must-see for outdoor lovers, Dry Hill offers stunning scenery and an adventurous atmosphere. Located about 6 miles from Sheffield, this preserve invites visitors to explore its natural beauty. Staying nearby provides easy access to this picturesque retreat, perfect for a day of adventure and relaxation.

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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

The Red Lion Inn

10/10 Excellent

"If you want a perfect New England experience, this is the place. The hotel is amazing, it’s older so don’t think you’re going to walk into a modern place, but don’t let that deter you, the vibe is great! Will definitely stay here again."

Quality Inn Great Barrington

10/10 Excellent

"A clean, well maintained, close to everything, motel. Would highly recommend and will stay again next time we are in the area."

Wilder House Berkshires

10/10 Excellent

"Wonderful stay! Intend to be back here."

Berkshires Untold

10/10 Excellent

"Love the property, room seemed a little tired since I was there last, about 3 years ago. Wish we could stay just one night instead of minimum two, as we often come just for a Tanglewood concert and stay only one night in town."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"I stayed in a townhouse, an upgrade from the room I booked. It was quiet and private, which I enjoyed, and more room than I needed. If my family's schedule had been different, I could have invited them over for a cookout (they live nearby). The townhouse was rather dated and I am afraid a bit dreary, with a lot of browns and beiges. But well-outfitted and convenient."

Quality Inn Lee - Lenox South

10/10 Excellent

"Very clean and comfortable. Some of the mechanicals are older but the rooms are quite fresh. Excellent location. Pretty good breakfast. Excellent value."

The Whitlock

10/10 Excellent

"The hotel staff were very friendly and helpful. There is ample parking and the location in town is great for walking to shops and restaurants. This is a very nice property."

Hampton Inn & Suites Berkshires-Lenox

8/10 Good

"Toilet was faulty but they gave us another room. Not much variety on the breakfast"

Little Cat Lodge

10/10 Excellent

"Quiet, clean and very good place to relax"

More cheap stays in Sheffield