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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, (43 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is NT$5,125
NT$5,724 total
includes taxes & fees
Mar 22 - Mar 23
Wilder House Berkshires

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
The price is NT$4,777
NT$5,336 total
includes taxes & fees
Mar 24 - Mar 25
The Berkshire Mountain Inn

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, (744 reviews)
"Simple and clean hotel"
United States
Vitor
The price is NT$3,408
NT$3,806 total
includes taxes & fees
Mar 30 - Mar 31
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (773 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is NT$4,841
NT$5,407 total
includes taxes & fees
Mar 30 - Mar 31
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (415 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is NT$3,344
NT$3,846 total
includes taxes & fees
Mar 21 - Mar 22
Locust Tree Bed and Breakfast LLC

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.8 out of 10, Exceptional, (23 reviews)
"Excellent local stay - would recommend to all"
United States
Gentian
The price is NT$7,516
NT$9,462 total
includes taxes & fees
Mar 22 - Mar 23
Prospect 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)
"Great place stay for our ski trip near by"
United States
wilson
The price is NT$2,139
NT$2,389 total
includes taxes & fees
Apr 5 - Apr 6
Quality Inn Great Barrington

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.4 out of 10, Exceptional, (136 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 NT$5,907
NT$6,480 total
includes taxes & fees
Mar 22 - Mar 23
Gedney Farm

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (879 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is NT$2,899
NT$3,950 total
includes taxes & fees
Mar 30 - Mar 31
Berkshire Mountain Lodge

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is NT$9,713
NT$11,721 total
includes taxes & fees
Mar 22 - Mar 23
The Old Inn On The Green

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (834 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
Monument Mountain Motel

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (672 reviews)
"Just wish they cleaned the rooms every day."
United States
Leanne
The price is NT$4,082
NT$4,560 total
includes taxes & fees
Mar 22 - Mar 23
Hilton Garden Inn Lenox Pittsfield

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (87 reviews)
"Amazing stuff they went above and beyond to accommodate on fridge cold day, good breakfast, hot tub is amazing "
United States
Paulo Eduardo
The price is NT$4,204
NT$4,696 total
includes taxes & fees
Apr 6 - Apr 7
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very Good, (18 reviews)
"Perfect "
United States
Zhigang
The price is NT$5,133
NT$5,807 total
includes taxes & fees
Mar 20 - Mar 21
The Millerton Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is NT$3,471
NT$3,808 total
includes taxes & fees
Mar 22 - Mar 23
Shaker Mill Inn

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (288 reviews)
"The restaurant, food and wait staff were fab!!! "
United States
Jacqueline
The price is NT$5,704
NT$6,559 total
includes taxes & fees
Mar 24 - Mar 25
Interlaken Inn & Resort

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (171 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is NT$4,959
NT$5,702 total
includes taxes & fees
Apr 2 - Apr 3
Blackberry River Inn

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Great stay, great breakfast"
United States
Peter
The price is NT$3,287
NT$3,671 total
includes taxes & fees
Apr 5 - Apr 6
Hampton Inn & Suites Berkshires-Lenox

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (876 reviews)
"Beautiful little quaint hotel. I will definitely be returning"
United States
Erin
The price is NT$2,224
NT$2,484 total
includes taxes & fees
Apr 2 - Apr 3
Berkshires Untold

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (40 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is NT$4,225
NT$4,719 total
includes taxes & fees
Apr 2 - Apr 3
East Rock Inn
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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 offers thrilling skiing opportunities and scenic trails for hiking and exploring nature.
  • Beautiful Parks and Lakes: Enjoy the stunning landscape with access to national parks, nature reserves, and serene lakes for relaxation.
  • Charming Accommodations: Experience a range of lodgings from cozy bed & breakfasts to agritourism properties tailored for families and pets.
  • Rich History and Culture: Discover the local history while strolling through picturesque neighborhoods and engaging with friendly locals.
  • Relaxing Spa Experiences: Unwind after adventures with rejuvenating spa treatments available in the area.

Find great hotels near Sheffield

Discover the charming accommodations in Sheffield, Massachusetts, where a mix of agritourism properties and cozy bed & breakfasts await. Whether you're traveling with family, seeking a pet-friendly stay, or looking for an adventurous vacation experience, Sheffield has a variety of options to suit your needs. Explore the best hotels and read reviews to find the perfect lodging for your getaway in this picturesque New England town.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled in the scenic Berkshires, this 3.5-star resort provides a welcoming atmosphere perfect for families and business travelers alike. With its child-friendly amenities such as an Arcade Game Room, Mini Golf, and a shared playground, the resort ensures that younger guests have plenty of entertainment. Spacious accommodations offer comfort and convenience, making it an ideal retreat for relaxation after a day of exploring the beautiful surroundings. Enjoy the blend of leisure and family-friendly activities that make this resort a standout choice for your vacation.
  • Quality Inn: Located just 9.7km from Sheffield, Quality Inn is the go-to destination for adventure seekers and business travelers. This hotel offers an array of exciting recreational activities nearby, including snow tubing, snowboarding, and hiking. Whether you're hitting the slopes or exploring the scenic trails, the hotel serves as a comfortable base for your adventures. With its focus on adventure sports and a welcoming atmosphere, Quality Inn is perfectly tailored for those looking to blend work with thrilling outdoor experiences.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Situated 11.3km from Sheffield, this hotel is a modern and inclusive choice for business travelers and the LGBTQIA community. Guests can expect a warm welcome and an environment that celebrates diversity. The hotel’s convenient access to local attractions and amenities ensures a comfortable stay, whether you are in town for work or leisure. Featuring contemporary furnishings and a commitment to guest satisfaction, Holiday Inn Express provides a great blend of comfort and community engagement.

Where to stay near Sheffield

Sheffield, Massachusetts, offers a delightful escape for adventure enthusiasts and history buffs alike. Explore scenic trails and outdoor activities that embrace the region's natural charm. Nearby towns provide family-friendly atmospheres perfect for a getaway with loved ones. Stroll through picturesque neighborhoods filled with friendly locals, and discover romantic spots ideal for couples. With a variety of vacation packages and attractions within walking distance, Sheffield is the perfect destination for a memorable experience.

  • The Berkshires: Nestled approximately 17.7km from Sheffield, The Berkshires is a picturesque region that draws visitors year-round for its stunning landscapes and outdoor adventures. With its peaks and valleys, this area is especially popular from June to August, when travelers flock to enjoy activities such as skiing and hiking. Notable attractions include serene lakes and majestic mountains, providing ample opportunities for exploration and relaxation. Whether you're hitting the slopes at a ski resort or attending a conference at a local venue, The Berkshires offers a blend of adventure and scenic beauty that is hard to resist.
  • Great Barrington: Located 9.7km from Sheffield, Great Barrington is a vibrant city known for its outdoor sports and adventure tourism. Similar to The Berkshires, visitor numbers peak from June to August, but this city also offers year-round activities, particularly for skiing enthusiasts. Enjoy the thrill of winter sports at nearby ski fields and resorts, or explore the beautiful parks and lakes that define the region. Great Barrington is a fantastic destination for those looking to experience the thrill of outdoor activities while enjoying a charming small-town atmosphere.
  • Ashley Falls: Just 6.4km away from Sheffield, Ashley Falls is a quaint city that attracts visitors seeking adventure and outdoor experiences. The area sees a moderate influx of tourists, with peak seasons in July to August and October. Here, you can indulge in skiing, motor racing, and other exciting sports activities. The proximity to national state parks and lakes makes Ashley Falls a great spot for nature lovers. Whether you're racing down the slopes or enjoying a peaceful day at the park, Ashley Falls offers a unique blend of excitement and tranquility.

Things to do near Sheffield

Sheffield, Massachusetts, offers a perfect getaway for adventure seekers and outdoor enthusiasts, featuring exciting activities like skiing at local resorts and exploring nearby ski fields. Visitors can unwind at various parks and enjoy rejuvenating spa experiences. Whether you’re hitting the slopes or relaxing in nature, Sheffield promises a memorable vacation filled with both excitement and tranquility.

Shopping

If you're up for a drive, Lee Premium Outlets, located 22.5km away, offers a variety of brand-name stores and great deals. Closer to Sheffield, you can explore the Berkshire Mountain Country Store and Hoffman's Pottery, both about 24.1km away, for unique gifts and souvenirs.

Recreation

At Lake Mansfield Park, enjoy serene walks and picnics surrounded by nature, perfect for relaxation. Music Mountain offers vibrant concerts that uplift your spirit, while Greenock Country Club provides an invigorating golf experience amidst picturesque landscapes, ideal for both sport and leisure enthusiasts.

Adventure

At Ski Butternut, located 8.0km from Sheffield, experience thrilling skiing and snowboarding in a vibrant winter atmosphere. Explore the scenic Housatonic River Walk, 9.7km away, for a refreshing hiking adventure amidst beautiful landscapes. For adrenaline junkies, Catamount Aerial Adventure Park, 12.9km from Sheffield, offers exciting ziplining and ropes courses.

Nightlife

In Sheffield, the Mahaiwe Performing Arts Center offers a charming mix of romance and culture just 9.7km away. Infinity Music Hall and Bistro, located 17.7km away, combines live music with a cozy bistro atmosphere. The Berkshire Theatre Festival, 19.3km away, enhances your night with captivating performances.

*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, plan your visit during the cheapest months of January or March to April, and aim for a Tuesday stay to enjoy lower hotel rates. Utilize Expedia to compare room rates, find great savings, and take advantage of flexible booking options. Consider bundling your hotel, flights, and activities for additional discounts. Explore free local attractions and use the affordable public transport available to navigate the area efficiently, ensuring a budget-friendly experience while enjoying the charm of 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: Expedia’s search tool lets you choose your budget, desired location, and other preferences. You can organize your results by sorting prices from lowest to highest, ensuring you see the most affordable hotels first. Additionally, you have the option to refine your search by hotel type; for instance, selecting the Eco-certified filter will display sustainable and environmentally-friendly hotels that you can book.
  • 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 perfect for adventure seekers and outdoor enthusiasts, offering stunning national parks, nature reserves, and beautiful lakes. Visitors can enjoy eco-friendly experiences while exploring the area's natural beauty. For those looking to stay nearby, there are several hotels near the Sheffield Botanical Gardens, making it easy to relax after a day of outdoor activities.

  • Taconic State Park: Just 12.9km from Sheffield, this national park offers breathtaking scenery and outdoor adventures. Hike through lush forests, explore scenic trails, and enjoy stunning views of the Taconic Mountains, making it a perfect spot for nature lovers and thrill-seekers alike.
  • Housatonic River: Located 9.7km away, the Housatonic River is ideal for outdoor activities. Experience the beauty of the river as you kayak, fish, or picnic along its banks, surrounded by picturesque landscapes and vibrant wildlife.
  • Ashley House: Situated within Sheffield, this charming museum showcases local culture and history. Explore its beautifully preserved architecture and learn about the region's past through engaging exhibits and guided tours.

Best time to go to Sheffield

The best time to visit Sheffield is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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

For your visit to Sheffield, Massachusetts, you have several airport options. Hartford, CT (BDL-Bradley Intl.) is the closest, located 59.5km away, with nearby hotels like the DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport. Albany, NY (ALB-Albany Intl.) is another option, situated 80.5km from Sheffield, offering hotels such as the Park Manor Hotel, 12.9km from the airport. Lastly, Newburgh, NY (SWF-Stewart Intl.) is 91.7km away, with hotels like The Dutchess Inn and Spa at Beacon, 9.7km from the airport. Each of these airports provides various transportation services to facilitate your travel.

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 Berkshires Untold. See all available top hotels, or 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: Provides free self parking, an indoor pool, and complimentary wireless internet access. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG and The Yankee, Trademark Collection by Wyndham 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 34 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 Housatonic River, Lime Kiln Farm Wildlife Sanctuary, and Magnolia Bluffs Casino. A couple of additional sights to add to your agenda are Drury Preserve and Ashley House. 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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