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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)
  • cleanliness
    Unwind in the Berkshires at this charming B&B with free weekend breakfast.
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is NT$6,077
NT$6,788 total
includes taxes & fees
Feb 8 - Feb 9
Wilder House Berkshires

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
  • cleanliness
    Enjoy views of the Berkshires at this comfortable retreat with seasonal outdoor pool.
"Very friendly staff comfy beds!"
United States
Giselle
The price is NT$2,921
NT$3,263 total
includes taxes & fees
Feb 11 - Feb 12
The Yankee, Trademark Collection by Wyndham

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, (730 reviews)
  • cleanliness
    Unwind in the Berkshires with indoor pool and free hot breakfast each morning.
"Great property, very accommodating. "
United States
Shanice
The price is NT$3,373
NT$3,768 total
includes taxes & fees
Feb 11 - Feb 12
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (444 reviews)
  • cleanliness
    Enjoy a relaxing Berkshires retreat with free breakfast and parking amenities.
"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 NT$3,793
NT$4,160 total
includes taxes & fees
Feb 8 - Feb 9
Shaker Mill Inn

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Modern lakeside retreat with 24-hour fitness and scenic Tanglewood location.
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is NT$3,082
NT$3,442 total
includes taxes & fees
Feb 24 - Feb 25
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,001 reviews)
  • cleanliness
    Experience a peaceful stay near Mahaiwe Performing Arts Center.
"This was a perfect place to stay. Reasonably priced, very clean, and the young lady who worked the front desk in the evening was super friendly. We will definitely book here again. "
United States
Jerome
The price is NT$2,385
NT$2,664 total
includes taxes & fees
Feb 22 - Feb 23
Quality Inn Great Barrington

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (819 reviews)
"Unbelieveably clean for the price."
United States
Micah
Monument Mountain Motel

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (830 reviews)
  • cleanliness
    Convenient Lenox motel offers outdoor pool and complimentary WiFi and parking.
"Staff was very friendly and helpful."
United States
Pamela
The price is NT$2,175
NT$2,430 total
includes taxes & fees
Feb 9 - Feb 10
Howard Johnson by Wyndham Lenox

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (567 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is NT$2,364
NT$2,641 total
includes taxes & fees
Feb 11 - Feb 12
Travelodge by Wyndham Great Barrington Berkshires

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (850 reviews)
  • cleanliness
    Experience Berkshires charm with onsite American dining and attentive service.
"So charming, clean, thoughtful touches and a really special place!"
United States
Juliana
The price is NT$2,783
NT$3,109 total
includes taxes & fees
Feb 9 - Feb 10
Berkshires Untold

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (665 reviews)
  • cleanliness
    Perfect setting for a Berkshires visit with an indoor pool and Asian dining.
" Nice staff - beautiful hotel!"
United States
MARY
The price is NT$4,321
NT$4,827 total
includes taxes & fees
Feb 27 - Feb 28
Hilton Garden Inn Lenox Pittsfield

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (18 reviews)
  • cleanliness
    Relax in the Berkshires with pool access and complimentary breakfast daily.
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is NT$4,382
NT$4,895 total
includes taxes & fees
Feb 22 - Feb 23
Element Lenox Berkshires

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (830 reviews)
  • cleanliness
    Berkshire getaway with 4 swimming pools offers seasonal outdoor retreat.
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is NT$3,547
NT$4,578 total
includes taxes & fees
Feb 9 - Feb 10
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (414 reviews)
  • cleanliness
    Experience the charming Locust Tree B&B in East Canaan with free breakfast.
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is NT$3,310
NT$3,807 total
includes taxes & fees
Feb 5 - Feb 6
Locust Tree Bed and Breakfast LLC

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (291 reviews)
  • cleanliness
    Serene lakeside escape with water activities and complimentary perks.
"A charming inn in the center of the Berkshires."
United States
Danny
The price is NT$4,551
NT$5,338 total
includes taxes & fees
Feb 6 - Feb 7
Lakehouse Inn

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,000 reviews)
  • cleanliness
    Serene Lee retreat a short drive from Tanglewood Music Center and local sights.
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is NT$2,653
NT$2,963 total
includes taxes & fees
Feb 22 - Feb 23
Quality Inn Lee - Lenox South

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
  • cleanliness
    Cozy Berkshires retreat minutes from Tanglewood with free parking and WiFi.
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is NT$1,844
NT$2,023 total
includes taxes & fees
Feb 5 - Feb 6
Pleasant Valley Motel West Stockbridge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (826 reviews)
  • cleanliness
    Experience the beauty of the Berkshires at a cozy lodge with golf access and pool.
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is NT$3,111
NT$4,179 total
includes taxes & fees
Feb 12 - Feb 13
Berkshire Mountain Lodge

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Convenient Lenox hotel with indoor pool near Tanglewood Music Center.
"The room and amenities were amazing. "
United States
Kathleen
The price is NT$3,758
NT$4,197 total
includes taxes & fees
Mar 1 - Mar 2
Hampton Inn & Suites Berkshires-Lenox

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (553 reviews)
  • cleanliness
    Explore scenic Great Barrington with free perks and helpful staff at this cozy motel.
"Great friendly staff"
United States
Pablo
The price is NT$3,468
NT$3,873 total
includes taxes & fees
Feb 5 - Feb 6
The Little Lion
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 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 Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG. 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: Features 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 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 Ashley House. A couple of additional sights to add to your agenda are Mount Everett State Reservation and Thom Reed UFO Monument Park. 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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