Book The Best Hotels in Sheffield, MA for 2026 from CA $108 - Fully Refundable Options

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Sheffield

Pet friendly

Hot tub

Apartment

Pool

Spa

Cottage

Family friendly

Cabin

Waterpark

Condo

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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.

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

1. Berkshire Mountain Lodge

Pittsfield

Robert

CA $110

CA $154 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 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.

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

Drue

CA $196

CA $219 total

includes taxes & fees

Sep 28 - Sep 29

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 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.

3. The Yankee Inn

Lenox

William

CA $147

CA $165 total

includes taxes & fees

Sep 28 - Sep 29

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.

4. Wilder House Berkshires

Sheffield

Mark

CA $270

CA $301 total

includes taxes & fees

Sep 27 - Sep 28

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

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

5. Prospect Berkshires

Egremont

Kellee

CA $459

CA $560 total

includes taxes & fees

Sep 23 - Sep 24

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 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.

6. Little Cat Lodge

Copake Falls

Kees

CA $251

CA $281 total

includes taxes & fees

Sep 23 - Sep 24

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 bar with wooden floors and shelves filled with bottles.

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

7. The Red Lion Inn

Stockbridge

James

CA $214

CA $309 total

includes taxes & fees

Sep 29 - Sep 30

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

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

8. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Linda

CA $164

CA $210 total

includes taxes & fees

Sep 29 - Sep 30

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.

9. Quality Inn Great Barrington

Great Barrington

Kimberly

CA $141

CA $158 total

includes taxes & fees

Oct 19 - Oct 20

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 breakfast area with a counter, coffee machine, and a display of pastries.

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

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

Great Barrington

Maria Dulce

CA $186

CA $208 total

includes taxes & fees

Oct 19 - Oct 20

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.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

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

Great Barrington

Bruce

CA $272

CA $304 total

includes taxes & fees

Sep 27 - Sep 28

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.

12. the Alander

Copake

Phil

CA $202

CA $226 total

includes taxes & fees

Sep 23 - Sep 24

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

13. The Little Lion

Great Barrington

Anne

CA $145

CA $162 total

includes taxes & fees

Oct 18 - Oct 19

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.

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

Lee

Ann M

CA $178

CA $199 total

includes taxes & fees

Sep 28 - Sep 29

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

A motel with a parking lot and several cars parked.

15. Monument Mountain Motel

Great Barrington

Victor

CA $108

CA $120 total

includes taxes & fees

Sep 27 - Sep 28

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 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.

16. Blackberry River Inn

Norfolk

Rachel

CA $210

CA $241 total

includes taxes & fees

Sep 27 - Sep 28

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

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

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.

17. Gedney Farm

Great Barrington

Terri

CA $322

CA $353 total

includes taxes & fees

Sep 23 - Sep 24

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

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

A covered porch with white railings and rocking chairs.

A dining room with a wooden table, chairs, a vase with flowers, and red curtains.

18. Locust Tree Bed and Breakfast LLC

East Canaan

Nicholas

CA $147

CA $169 total

includes taxes & fees

Sep 27 - Sep 28

A bedroom with a large bed, a chair, and a window with curtains.

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.

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.

19. The White Hart

Salisbury

William

CA $482

CA $554 total

includes taxes & fees

Sep 28 - Sep 29

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.

20. East Rock Inn

Great Barrington

ERIK

CA $222

CA $247 total

includes taxes & fees

Oct 22 - Oct 23

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Sheffield attractions

Ashley House

You can learn about the history of Sheffield with a trip to Ashley House. Discover the area's breweries or seek out the hiking trails.

See properties

Thom Reed UFO Monument Park

8.0/10 (1 review)

Explore the great outdoors at Thom Reed UFO Monument Park, a lovely green space in Sheffield. Make some time to visit the casinos while you're in the area.

See properties

Bartholomews Cobble

Explore the great outdoors at Bartholomews Cobble, a lovely green space in Sheffield. Make some time to visit the casinos while you're in the area.

See properties

Drury Preserve

You can take time to visit Drury Preserve during your travels to Sheffield. Make some time to visit the casinos while you're in the area.

See properties

Bartholomew's Cobble

10.0/10 (1 review)

You can take time to visit Bartholomew's Cobble during your travels to Sheffield. Make some time to visit the casinos while you're in the area.

See properties

Lime Kiln Farm Wildlife Sanctuary

You can take time to visit Lime Kiln Farm Wildlife Sanctuary during your travels to Sheffield. Make some time to visit the casinos while you're in the area.

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

Top Sheffield Hotel Reviews

Quality Inn Great Barrington

10/10 Excellent

"Good place"

Berkshires Untold

8/10 Good

"Liked he cleanliness. Room was very cold and no heat was available."

The Yankee Inn

10/10 Excellent

"The room was spacious, clean and comfortable. I will definitely stay there again."

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

10/10 Excellent

"The room was clean and perfect when we arrived! The pool area was a big hit with my boys and the breakfast the next morning was amazing!"

The Red Lion Inn

10/10 Excellent

"This is a wonderful, historic inn. Check out the Red Lion Den for music. We heard a terrific local group. We ate in the Tavern and the food was tasty. This is not a luxurious place. It dates back to the 1700s. But it is really charming. My friends and I stayed in a suite in an out building. We had a low-ceiled living room downstairs, which was a. great place to talk and catch up. The bedroom situation was a little funky because the bathroom was right next to the bed in one of two sleeping areas upstairs and the door really squeaked when it opened and closed. But that was about our only complaint. I'd be delighted to return."

Howard Johnson by Wyndham Lenox

10/10 Excellent

"Good"

Wilder House Berkshires

10/10 Excellent

"Brad was very hospitable and helpful with advice on what to do. And the breakfasts were great."

More cheap stays in Sheffield

Quality Inn Great Barrington

372 Main Street Great Barrington MA

CA $141

CA $158 total

Oct 19 - Oct 20

includes taxes & fees

8.6/10 Excellent! (1,010 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

CA $147

CA $165 total

Sep 28 - Sep 29

includes taxes & fees

9.2/10 Wonderful! (1,004 reviews)

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA

CA $153

CA $171 total

Oct 21 - Oct 22

includes taxes & fees

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

1055 South Street Pittsfield MA

CA $166

CA $185 total

Oct 20 - Oct 21

includes taxes & fees

9.4/10 Exceptional! (216 reviews)

Holiday Inn Express Hotel & Suites Great Barrington by IHG

415 Stockbridge Rd Great Barrington MA

CA $186

CA $208 total

Oct 19 - Oct 20

includes taxes & fees

The Whitlock

16 Church St Lenox MA

CA $194

CA $217 total

Sep 23 - Sep 24

includes taxes & fees

Hotels in Sheffield with star rating

Find out more about Sheffield

Top reasons to visit Sheffield

Outdoor Adventures: Sheffield is a haven for outdoor enthusiasts, offering activities like skiing, hiking, and exploring picturesque lakes and national parks.
Historical Charm: The town boasts a rich historical background, presenting visitors with charming architecture and a friendly atmosphere.
Family-Friendly Activities: Sheffield offers diverse attractions suitable for families, ensuring fun for travellers of all ages.
Scenic Beauty: Enjoy the stunning natural landscapes and serene scenery that Sheffield has to offer.
Comfortable Accommodations: A variety of lodging options cater to different preferences, from pet-friendly to adventure-filled stays.

Find great hotels near Sheffield

Discover a charming getaway in Sheffield, Massachusetts, where a variety of accommodations await to cater to every traveller's desires. Whether you're seeking a pet-friendly retreat, family-friendly services, or an adventure-filled experience, Sheffield's hotels offer comfort and convenience. Explore the best options available to ensure a memorable stay in this picturesque town.

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Experience a family-friendly adventure at the 3.5-star Holiday Inn Club Vacations Oak n’ Spruce Resort, rated 9.0 by guests. Located 19.3km from Sheffield, this resort is perfect for those seeking winter sports and outdoor activities. With amenities like ski lessons, snowboarding, and hiking, adventure awaits right at your doorstep. Families will appreciate the onsite mini-golf, arcade game room, and a playground for kids. This resort is designed to accommodate guests of all ages, making it an ideal choice for a fun-filled vacation.
Quality Inn Great Barrington: For budget-conscious travellers, the Quality Inn Great Barrington offers a cozy experience just 9.7km from Sheffield. With a guest rating of 8.4, this hotel is perfect for those seeking adventure or business travel. Guests can enjoy nearby activities such as snowshoeing, cross-country skiing, and snow tubing. The hotel provides a comfortable stay with essential amenities, ensuring a pleasant visit without breaking the bank. It’s an excellent base for exploring the Berkshires while keeping the focus on value and convenience.
Holiday Inn Express Hotel & Suites Great Barrington by IHG: Located 11.3km from Sheffield, the Holiday Inn Express Hotel & Suites Great Barrington is a budget-friendly option with a guest rating of 8.8. This hotel caters to business travellers while still providing a welcoming atmosphere for leisure guests. It features modern accommodations and essential amenities, making it an ideal choice for those who need to stay connected while on the go. Enjoy a comfortable night’s sleep and start your day with a complimentary breakfast before exploring the picturesque Berkshires.

Where to stay near Sheffield

Sheffield, Massachusetts, offers a delightful blend of outdoor adventures and rich historical charm. Whether you're skiing on nearby slopes or exploring the heart of Sheffield, you'll find the city’s friendly atmosphere inviting. Enjoy family-friendly activities, serene scenery, and romantic spots in the Sheffield city centre. Don't miss the opportunity to experience the luxury accommodations and vibrant neighborhoods that make Sheffield a perfect vacation destination for all types of travellers.

Great Barrington: Located 9.7km from Sheffield, Great Barrington is a charming city that attracts visitors year-round, particularly from June to August. Known for its outdoor adventures, the area is a haven for skiing enthusiasts, with numerous ski fields and resorts nearby. The picturesque landscape features stunning lakes and mountains, making it perfect for nature lovers. Don't miss the opportunity to explore the local national state park, where you can hike and enjoy the breathtaking scenery.
The Berkshires: Situated 17.7km from Sheffield, The Berkshires is renowned for its natural beauty and outdoor recreational activities. Visitors flock here during the summer months, but the area offers year-round attractions. With its diverse landscape, The Berkshires is ideal for skiing, hiking, and enjoying the serene lakes. Outdoor enthusiasts will appreciate the picturesque ski resorts and fields, while cultural aficionados can attend events at local conference venues that showcase the region's artistic flair.
South Egremont: Just 8.0km from Sheffield, South Egremont is a delightful city that offers a mix of adventure and relaxation. Like its neighbours, it experiences a peak in visitor numbers from June to August, drawing those eager to ski and explore the outdoors. The area is surrounded by beautiful lakes and mountains, providing a perfect backdrop for various activities. Outdoor enthusiasts can find ski resorts and fields nearby, making it an excellent destination for sports lovers seeking excitement in the great outdoors.

Things to do in Sheffield

Sheffield, Massachusetts, is perfect for outdoor enthusiasts seeking adventure and excitement. Visitors can enjoy thrilling ski experiences at local ski resorts and fields, as well as various outdoor activities. The area also boasts attractive city sights, beautiful golf courses, and numerous recreational facilities, making it an ideal destination for those looking to explore its natural beauty and enjoy a range of exciting rides.

Shopping

Sheffield offers charming local shops like the Sheffield General Store for unique gifts and souvenirs. If you're up for a drive, visit the Berkshire Mall in Lanesborough, about 24.1km away, where you can find a variety of retail stores and dining options.

Recreation

The Kripalu Centre for Yoga & Health offers transformative wellness retreats, featuring yoga classes, meditation, and healthy cuisine in a tranquil setting. Explore the beautiful Berkshire mountains on hiking trails or unwind at local spas for rejuvenating treatments, creating a perfect balance of relaxation and adventure.

Adventure

In Sheffield, explore the breathtaking landscapes of the Berkshires with hiking at Mount Everett State Reservation, where panoramic views await. Enjoy thrilling canoeing on the Housatonic River, or immerse yourself in nature at the nearby Bash Bish Falls for a refreshing adventure.

Nightlife

Experience Sheffield's charming nightlife at The Castle Street Café, where delicious local cuisine meets a relaxed vibe. For a lively evening, visit The Sheffield Inn, offering great drinks and live music, perfect for mingling with locals and fellow travellers alike.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Sheffield

The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Sheffield are January and March to April, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Sheffield is Tuesday. The most expensive day to stay in Sheffield is Saturday.
Find cheap hotels on Expedia: Utilize Expedia’s search tool to customize your preferences, such as your budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly accommodations currently available. To find the best prices and offers, simply sort the price filter from lowest to highest.
Consider bundling your trip: You can save money by combining your hotel stay in Sheffield with your flights and activities through an Expedia package deal.

Find the best attractions in and around Sheffield

Sheffield, Massachusetts, is a fantastic destination for outdoor enthusiasts seeking adventure and eco-friendly experiences. With its stunning national parks, serene nature reserves, and picturesque lakes, visitors can indulge in various activities, from skiing to hiking. Whether you're looking for a thrilling outdoor vacation or a peaceful retreat in nature, Sheffield offers a diverse range of attractions that cater to all types of travellers.

Ashley House: Experience the rich cultural heritage of Sheffield at the Ashley House museum. This historic site offers a glimpse into the past with its beautifully preserved architecture and engaging exhibits that reflect local history and culture.
Taconic State Park: Just 12.9km from Sheffield, Taconic State Park is perfect for adventure enthusiasts. Enjoy breathtaking scenery, hiking trails, and outdoor activities that allow you to immerse yourself in the stunning natural beauty of the region.
Housatonic River: Located 9.7km from Sheffield, the Housatonic River offers picturesque views and opportunities for outdoor recreation. Whether kayaking or simply enjoying a peaceful walk along the river, you’ll find a connection with nature here.

Best time to go to Sheffield

The best time to visit Sheffield can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Sheffield falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Sheffield falls in January, visitor numbers are average and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	23.2°F (-4.9°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
February	24.8°F (-4.0°C)	Light Rain	Mostly Cloudy	Slightly Low	Average
March	32.5°F (0.3°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	44.2°F (6.8°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
May	55.9°F (13.3°C)	Light Rain	Mostly Sunny	Average	Average
June	63.7°F (17.6°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	69.8°F (21.0°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	67.8°F (19.9°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	60.8°F (16.0°C)	Light Rain	Mostly Sunny	Slightly High	Average
October	49.8°F (9.9°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	37.8°F (3.2°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	29.7°F (-1.3°C)	Light Rain	Mostly Cloudy	Slightly Low	Average

The nearest major airports for your trip to Sheffield

If you're planning a trip to Sheffield, Massachusetts, there are several major airports you can consider. New York's LaGuardia Airport (LGA) is 154.5km away, with luxury options like The Plaza and The Pierre, both 8.0km from the airport, offering shuttle services. Hartford's Bradley International Airport (BDL) is closer at 59.5km, with the DoubleTree by Hilton just 1.6km away, providing convenient access. ALBany International Airport (ALB), located 80.5km from Sheffield, has several good hotels, including The Landing Hotel at Rivers Casino, 12.9km from the airport. These airports offer a range of transportation options to ensure a smooth journey to your destination.

Frequently asked questions

What is the best area to stay in Sheffield?

The best area to stay in Sheffield, Massachusetts, is the town centre, particularly around Main Street (Route 7).Sheffield's town centre is a pleasant and convenient base for exploring the Southern Berkshires. Main Street is where you'll find a selection of antique shops, local eateries, and a few small galleries. The town maintains a relaxed, rural character, making it easy to unwind.Couples looking for a tranquil getaway will appreciate the quiet charm of Sheffield. Many accommodations here offer a peaceful setting, often with views of the surrounding hills, great for relaxing after a day of exploring the region's art and nature. It's also a great base for visiting nearby towns such as Great Barrington.For those interested in outdoor activities and nature, staying in or just outside the town centre provides easy access to local hiking trails and scenic drives.

What are the best hotels in Sheffield that travellers recommend?

For a highly recommended hotel in Sheffield, Massachusetts, consider the Wilder House Berkshires.The Wilder House Berkshires, with an outstanding 9.8 rating, is praised by guests for its comfortable and clean rooms. Travellers particularly enjoy the great and delicious complimentary cooked breakfast. The hotel also offers premium bedding, air conditioning, and free self-parking, ensuring a convenient and pleasant stay.

What are the best family hotels in Sheffield?

For families travelling to Sheffield, the Wilder House Berkshires is an excellent choice.This highly-rated accommodation, with an impressive 9.8 review score, offers a welcoming stay for families. Guests consistently praise the comfortable and clean rooms, ensuring a pleasant environment for everyone. A significant advantage for families is the complimentary breakfast, including cooked options, which guests describe as great and delicious. Free toiletries, free WiFi, and free self-parking add to the convenience and value. The availability of a free crib further highlights its family-friendly focus, making it easier for parents travelling with infants.

What hotels in Sheffield offer free breakfast?

For hotels in Sheffield that provide complimentary breakfast, the Wilder House Berkshires is an excellent option.This highly-rated property, with an impressive 9.8 review score, offers both free breakfast and free cooked breakfast, which guests consistently describe as great and delicious. The rooms are noted for being comfortable and clean, and the hotel also provides free WiFi, free self-parking, and premium bedding. Additionally, it is conveniently located just 10.2 km from the Housatonic River.

What are the best budget hotels in Sheffield?

For a great budget hotel in Sheffield, consider the Wilder House Berkshires.The Wilder House Berkshires has an exceptional review rating of 9.8. Guests consistently mention the comfortable and clean rooms, along with the great and delicious breakfast. This hotel provides a range of complimentary amenities, including free cooked breakfast, free toiletries, free WiFi, and free self-parking. The rooms also feature premium bedding and air conditioning for added comfort. It is located approximately 10.2 km from the Housatonic River. View all budget hotels in Sheffield

When is the best time to go to Sheffield?

The best time to visit Sheffield, Massachusetts, depends on your preferences for outdoor activities and the region's natural beauty.For those who enjoy warm weather and outdoor adventures, the summer months from June to August are ideal. The Berkshires are lush and green during this period, superb for hiking, cycling, and enjoying the numerous lakes and rivers. You'll find many local farms offering fresh produce, and outdoor events are plentiful.If you're particularly interested in the stunning autumn foliage, late September through October is the most picturesque time to visit. The hillsides transform into a spectacular display of reds, oranges, and yellows, making it superb for scenic drives and photography. This period is very popular, so booking accommodation well in advance is recommended.For winter sports enthusiasts, December through March offers opportunities for skiing, snowboarding, and snowshoeing at nearby resorts. The landscape is often covered in snow, creating a serene and beautiful setting, though some smaller shops and attractions might have reduced hours.Spring, from April to May, sees the awakening of the landscape with blooming flowers and budding trees.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Sheffield.

How much is the nightly rate at a Sheffield hotel?

Prices for hotels in Sheffield often vary, but you can find a great deal from CA $108 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Explore a world of travel with Expedia

The Berkshires Vacation Rentals

Book Hotels in Sheffield on Expedia.com

Find hotels in Sheffield, MA from CA $108

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Sheffield

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Sheffield hotels

1. Berkshire Mountain Lodge

2. Berkshires Untold

3. The Yankee Inn

4. Wilder House Berkshires

5. Prospect Berkshires

6. Little Cat Lodge

7. The Red Lion Inn

8. Holiday Inn Club Vacations Oak 'n Spruce Resort

9. Quality Inn Great Barrington

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

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

12. the Alander

13. The Little Lion

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

15. Monument Mountain Motel

16. Blackberry River Inn

17. Gedney Farm

18. Locust Tree Bed and Breakfast LLC

19. The White Hart

20. East Rock Inn

Stay near popular Sheffield attractions

Ashley House

Thom Reed UFO Monument Park

Bartholomews Cobble

Drury Preserve

Bartholomew's Cobble

Lime Kiln Farm Wildlife Sanctuary

Learn more about Sheffield

Top Sheffield Hotel Reviews

Quality Inn Great Barrington

Berkshires Untold

The Yankee Inn

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

The Red Lion Inn

Howard Johnson by Wyndham Lenox

Wilder House Berkshires

More cheap stays in Sheffield

Quality Inn Great Barrington

The Yankee Inn

Quality Inn Lee - Lenox South

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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

The Whitlock

Hotels in Sheffield with star rating

Find out more about Sheffield

Top reasons to visit Sheffield

Find great hotels near Sheffield

Where to stay near Sheffield

Things to do in Sheffield

Booking tips and Expedia advantages for Sheffield

Find the best attractions in and around Sheffield

Best time to go to Sheffield

The nearest major airports for your trip to Sheffield

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app