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Our top choices for Sheffield hotels

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (42 reviews)
"It was a very pleasant hybrid of a classic BnB with the privacy of an air BnB. Host was on point and communicative. We loved hanging out downstairs in the living room(s). Breakfast was fabulous "
United States
Evan M
Wilder House Berkshires

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (722 reviews)
"Always love staying here. The staff is fantastic, amenities are great, and the breakfast is just lovely. Will be returning soon!"
United States
Domenic
The price is SAR 401
SAR 448 total
includes taxes & fees
22 Jan - 23 Jan
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18 reviews)
"It was clean and environment is relaxing."
United States
KEYA
The price is SAR 632
SAR 832 total
includes taxes & fees
27 Jan - 28 Jan
Prospect Berkshires

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (134 reviews)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
The price is SAR 696
SAR 763 total
includes taxes & fees
18 Jan - 19 Jan
Gedney Farm

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (761 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is SAR 506
SAR 565 total
includes taxes & fees
29 Jan - 30 Jan
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,000 reviews)
"My go to place for my ski weekends"
United States
Ryan
The price is SAR 264
SAR 295 total
includes taxes & fees
5 Feb - 6 Feb
Quality Inn Great Barrington

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is SAR 1,144
SAR 1,380 total
includes taxes & fees
18 Jan - 19 Jan
The Old Inn On The Green

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is SAR 394
SAR 453 total
includes taxes & fees
18 Jan - 19 Jan
Locust Tree Bed and Breakfast LLC

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (817 reviews)
"Unbelieveably clean for the price."
United States
Micah
Monument Mountain Motel

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (37 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is SAR 491
SAR 548 total
includes taxes & fees
25 Jan - 26 Jan
East Rock Inn

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
7.4 out of 10, Good, (10 reviews)
"Beautiful property, only stayed one night for business but it was very nice. Great burger at the restaurant downstairs! Possibly one of the best burgers I’ve ever had!"
United States
Jason
The price is SAR 604
SAR 684 total
includes taxes & fees
19 Jan - 20 Jan
The Millerton Inn

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (74 reviews)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
The price is SAR 460
SAR 513 total
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (566 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is SAR 281
SAR 314 total
includes taxes & fees
19 Jan - 20 Jan
Travelodge by Wyndham Great Barrington Berkshires

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (548 reviews)
"Perfect for pets "
United States
Maria
The price is SAR 413
SAR 461 total
includes taxes & fees
18 Jan - 19 Jan
The Little Lion

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (166 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is SAR 616
SAR 709 total
includes taxes & fees
19 Jan - 20 Jan
Blackberry River Inn

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (811 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is SAR 370
SAR 497 total
includes taxes & fees
1 Feb - 2 Feb
Berkshire Mountain Lodge

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (441 reviews)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is SAR 405
SAR 444 total
includes taxes & fees
21 Jan - 22 Jan
Shaker Mill Inn

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (155 reviews)
"This inn was very quaint and welcoming. It was a nice inn for the value. "
United States
Jacqueline
The price is SAR 794
SAR 913 total
includes taxes & fees
18 Jan - 19 Jan
Cornwall Inn and Lodge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (16 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is SAR 521
SAR 582 total
includes taxes & fees
25 Jan - 26 Jan
Element Lenox Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Sheffield attractions

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.

FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

Top Sheffield Hotel Reviews

More cheap stays in Sheffield

Hotels in Sheffield with star-rating

Find out more about Sheffield

Top reasons to visit Sheffield

  • Outdoor Adventures: Sheffield is ideal for thrill-seekers, offering skiing, hiking, and eco-friendly experiences in stunning natural settings.
  • Scenic Parks: Explore picturesque parks and nature reserves that provide perfect spots for relaxation and outdoor activities.
  • Charming Accommodations: Enjoy a variety of lodging options, from cozy bed & breakfasts to unique agritourism properties.
  • Rich History: Discover Sheffield's fascinating history while enjoying its family-friendly and romantic spots.
  • Botanical Gardens: Visit the Sheffield Botanical Gardens for a peaceful retreat and beautiful landscapes.

Find great hotels near Sheffield

Discover a charming selection of accommodations in Sheffield, Massachusetts, perfect for your getaway. From cozy bed & breakfasts to unique agritourism properties, Sheffield offers a variety of lodging options to suit your needs. Whether you're traveling with pets, seeking adventure, or planning a family vacation, you'll find the best hotels here, complete with helpful reviews and essential amenities for a comfortable stay.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled in the scenic Berkshires, this 3.5-star resort is a perfect getaway for families and winter sports enthusiasts. Just 19.3km from Sheffield, the resort welcomes LGBTQIA travelers, offering a familial atmosphere with a variety of kid-friendly amenities such as an arcade game room, playground, and onsite mini-golf. The resort's proximity to ski lifts and shuttles makes it an ideal choice for those looking to hit the slopes. Guests can enjoy spacious accommodations and a host of recreational activities, ensuring a memorable family vacation experience.
  • Quality Inn: Located 9.7km from Sheffield, Quality Inn is the ideal choice for adventure seekers and business travelers. With a focus on recreation, the hotel offers easy access to nearby skiing, snowboarding, and snow tubing. Guests can take advantage of the hotel's adventure sports options, ensuring an exhilarating stay. The property balances comfort and convenience, providing essential amenities for business needs, making it a practical choice for those traveling for work or leisure.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Situated 11.3km from Sheffield, the Holiday Inn Express Hotel & Suites is perfect for LGBTQIA-friendly business travelers. This modern hotel combines comfort with functionality, offering well-appointed rooms and essential services tailored for corporate guests. Its affiliation with LGBTQI travel guides emphasizes an inclusive atmosphere. Guests can enjoy complimentary breakfast, high-speed Wi-Fi, and convenient access to local attractions, making it a great base for both work and exploration.

Where to stay near Sheffield

Sheffield, Massachusetts, offers a perfect blend of adventure and relaxation, making it an ideal getaway for travelers. Explore its rich history while enjoying outdoor activities like skiing and hiking. Nearby towns provide a charming atmosphere with scenic views, family-friendly options, and romantic spots. Discover the best places to visit and enjoy Sheffield vacation packages that cater to all ages, ensuring an unforgettable experience filled with friendly people and stunning landscapes.

  • The Berkshires: Located 17.7km from Sheffield, The Berkshires is a picturesque region renowned for its stunning landscapes and outdoor activities. Visitors flock here year-round, especially during the summer months of June to August, to indulge in adventures like skiing, hiking, and enjoying the scenic beauty of the lakes and mountains. The area boasts ski fields and resorts that cater to winter sports enthusiasts, while summer brings opportunities for hiking and exploring local parks. With its charming small towns and cultural venues, The Berkshires is a perfect destination for those seeking both relaxation and adventure.
  • Great Barrington: Situated 9.7km from Sheffield, Great Barrington is a vibrant city that attracts visitors with its blend of outdoor sports and cultural experiences. The peak travel season runs from June to August, when outdoor enthusiasts come to enjoy skiing and other adventure sports. The city is surrounded by beautiful lakes and mountains, making it an ideal spot for nature lovers. Visitors can explore parks and participate in various activities, ensuring a fun-filled experience. Great Barrington also offers a lively downtown with shops, restaurants, and art galleries that showcase local talent.
  • Ashley Falls: Only 6.4km from Sheffield, Ashley Falls is a charming city that offers a mix of outdoor activities and sports experiences. While it sees moderate seasonal travel, with peak times in July to August and October, visitors are drawn to its ski fields and motor racing events. The city is close to beautiful lakes and a national state park, providing ample opportunities for hiking and exploration. Ashley Falls combines the thrill of outdoor sports with a laid-back atmosphere, making it an appealing destination for families and adventure seekers alike.

Things to do near Sheffield

Sheffield, Massachusetts, offers a range of activities perfect for adventure enthusiasts and outdoor lovers. Visitors can enjoy skiing at local resorts and ski fields, while also exploring the area's picturesque parks. For those seeking relaxation, a spa show is a must-see, making Sheffield an ideal destination for both thrill-seekers and those looking to unwind.

Shopping

In Sheffield, you can visit local shops and boutiques for unique souvenirs. If you're up for a drive, check out Lee Premium Outlets, located 22.5km away, offering a variety of brands. Also, consider the Berkshire Mountain Country Store and Hoffman's Pottery, both located 24.1km away.

Recreation

At Lake Mansfield Park, experience serenity amidst nature with scenic walking trails and peaceful picnic spots. Enjoy live performances at Music Mountain, where the vibrant atmosphere enhances your musical journey. For sports enthusiasts, Greenock Country Club offers a picturesque golf course perfect for a relaxing day outdoors.

Adventure

Experience thrilling skiing at Ski Butternut, located 8.0km from Sheffield, where you can enjoy the vibrant sports atmosphere. Hike the scenic Housatonic River Walk, 9.7km away, for breathtaking views. For an adrenaline rush, tackle the zipline course at Catamount Aerial Adventure Park, situated 12.9km from Sheffield.

Nightlife

In Sheffield, the nightlife is vibrant with options like the Mahaiwe Performing Arts Center, just 9.7km away, and the Infinity Music Hall and Bistro, 17.7km away, offering romantic and cultural experiences. Don't miss the Berkshire Theatre Festival, 19.3km from Sheffield, for an unforgettable evening of entertainment.

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

Booking tips and Expedia advantages for Sheffield

To save money on your trip to Sheffield, Massachusetts, consider visiting during the cheaper months of January or March to April, when accommodation prices drop. Tuesdays are the least expensive days to stay, while Saturdays tend to be pricier. Use Expedia to compare room rates and find great deals by filtering from lowest to highest prices. Additionally, look for package options that combine your hotel, flights, and activities for further savings. Don't forget to explore free local attractions during your stay to enhance your experience without breaking the bank.

  • 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 refine your options based on your budget, preferred location, and desired hotel type. To find the best prices and deals, simply arrange 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 by purchasing a package through Expedia.

Find the best attractions in and around Sheffield

Sheffield, Massachusetts, is perfect for adventure seekers and outdoor enthusiasts. With attractions like national parks, nature reserves, and lakes, visitors can enjoy eco-friendly experiences and thrilling activities. For a comfortable stay, consider looking for hotels near the Sheffield Botanical Gardens, which offer a peaceful retreat amidst nature. Whether you’re skiing or hiking, Sheffield promises an unforgettable outdoor vacation.

  • Taconic State Park: Located 12.9km from Sheffield, Taconic State Park offers breathtaking outdoor scenery and adventure. Explore lush forests, hiking trails, and stunning views of the Taconic Mountains, perfect for nature lovers and outdoor enthusiasts.
  • Housatonic River: Just 9.7km away, the Housatonic River is a serene spot for outdoor activities. Enjoy kayaking, fishing, or simply relaxing along the riverbank while taking in the picturesque landscape that surrounds this beautiful waterway.
  • Ashley House: Situated within Sheffield, the Ashley House is a charming museum that showcases local history and culture. Discover the rich heritage of the area through exhibits and guided tours in this beautifully preserved historic home.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly CloudyAverageSlightly Low
February24.8°F (-4.0°C)Light RainMostly CloudySlightly LowAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyAverageAverage
June63.7°F (17.6°C)Light RainMostly SunnySlightly HighAverage
July69.8°F (21.0°C)Light RainMostly SunnySlightly HighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnyAverageSlightly High
September60.8°F (16.0°C)Light RainMostly SunnySlightly HighAverage
October49.8°F (9.9°C)Light RainMostly SunnyAverageSlightly High
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowAverage
December29.7°F (-1.3°C)Light RainMostly CloudySlightly LowAverage

The nearest major airports for your trip to Sheffield

If you're planning to visit Sheffield, Massachusetts, you have several airport options. Hartford, CT (BDL-Bradley Intl.) is located 59.5km away, with nearby hotels like DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport, and Marriott Hartford Downtown, 19.3km away. ALBany, NY (ALB-Albany Intl.), situated 80.5km from Sheffield, offers accommodations such as Park Manor Hotel and DoubleTree by Hilton Schenectady Downtown, both 12.9km away. Newburgh, NY (SWF-Stewart Intl.) is 91.7km from Sheffield, with options like The Dutchess Inn and Spa at Beacon, 9.7km from the airport. Transportation services are available from these hotels to their respective airports.

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 The Yankee, Trademark Collection by Wyndham. See all available top hotels, or vacation rentals in Sheffield.
What are some of the best vacation home rentals that Sheffield has to offer?
Peace and quiet on the lake: This vacation home rental outside of Sheffield is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind. 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: Features free self parking, an indoor pool, and complimentary wireless internet access. The Yankee, Trademark Collection by Wyndham and Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG 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 Magnolia Bluffs Casino, Housatonic River, and Drury Preserve. A couple of additional sights to add to your agenda are Ashley House and Mount Everett State Reservation. 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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