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

Sheffield hotels from HK$692

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Stay near popular Sheffield attractions

Sheffield

Why not roll the dice with a visit to Magnolia Bluffs Casino during your time in Sheffield? Discover the area's breweries or seek out the hiking trails.
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Ashley House

Built in 1735, the Ashley House is where Elizabeth Freeman successfully sued for her freedom, helping end slavery in Massachusetts. Tour the historic rooms and learn about this pivotal chapter in American history.
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Bartholomews Cobble

Twin rocky knolls form this National Natural Landmark, home to one of North America's most diverse fern collections. Explore five miles of trails through forests and riverbanks for exceptional wildlife viewing.
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Thom Reed UFO Monument Park

8.0/10 (1 review)
America's first officially documented UFO encounter is commemorated at this riverside park in Sheffield. Explore plaques about the Reed family's 1969 experience while enjoying Housatonic River views.
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Bartholomew's Cobble

10.0/10 (1 review)
This National Natural Landmark features twin rocky knolls and North America's most diverse fern collection. Explore its trails through varied ecosystems while watching for peregrine falcons and rare plants.
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Drury Preserve

Explore diverse ecosystems along a serene 2.4-mile trail through hemlock forests and calcareous wetlands. Cross wooden boardwalks to a tranquil pond where great blue herons and other wildlife await.
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Lime Kiln Farm Wildlife Sanctuary

This wildlife sanctuary showcases diverse plant species across limestone ridges and conifer forests. Explore trails to spot numerous butterfly species and Pileated Woodpeckers in the tranquil Berkshires landscape.
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Learn more about Sheffield

Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green.

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

Top Sheffield Hotel Reviews

The Whitlock

The Whitlock

8/10 Good
"It's a unique property, a well-converted old mansion. There is no closet, and the floors slope a bit in the rooms, but it's a great room. I think bringing back a real restaurant to the property would be good as I really didn't know what was going on with that Tavern space."
Kimberly 2-night trip
Posted 1 hour ago
The Whitlock
Berkshires Untold

Berkshires Untold

10/10 Excellent
"Pleasant stay and Sarah made a bouquet of flowers for my daughter’s birthday..a fellow Leo!"
Marion 1-night trip
Posted 12 hours ago
Berkshires Untold
Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Very nice stay. Room can be a bit noisy. Overall great experience."
Stephen 2-night trip
Posted 13 hours ago
Berkshire Mountain Lodge
The Little Lion

The Little Lion

10/10 Excellent
"Clean, convenient, remotely operated by the owner, the Red Lion, a short distance away. We could use all the amenities offered by the Red Lion (meals, pool, hot tub) while staying at the much more reasonable Little Lion. A great bargain for Stockbridge!"
Joyce 1-night trip
Posted 16 hours ago
The Little Lion
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

8/10 Good
"The location just off busy route 20 was a minus, especially since it is difficult to make a left hand turn out of the property with the heavy traffic. The hotel itself was clean, modern and comfortable. All staff were friendly and helpful. The breakfast was generous and well prepared/presented. We enjoyed the pool, hot tub and the exercise room."
Sharon G. 1-night trip
Posted 16 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

8/10 Good
"The breakfast offerings were fair"
Maria 2-night trip
Posted 17 hours ago
Hampton Inn & Suites Berkshires-Lenox
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"Very nice, clean, good breakfast. Only complaint was that it was very expensive because we booked last minute and it the peak season. I would stay again but not at the price we were charged."
Josephine 2-night trip
Posted 18 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"The location was excellent, and the roads between Lee and Stockbridge, and in a lovely, secluded area. The rooms were spacious, ours included a living room, dining and kitchen area, and upstairs bedroom with spacious closet and bathroom. The price was reasonable. It was very quiet and well maintained. There was a lot for kids to do -- swimming pool and movies. We would go there again."
Pam 6-night trip
Posted 19 hours ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

8/10 Good
"Bed not very comfortable.."
Dennis 1-night trip
Posted 3 days ago
The Cornell Inn, Lenox & The Berkshires

More cheap stays in Sheffield

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
HK$620
HK$692 total
31 Aug - 1 Sept
includes taxes & fees
7.6/10 Good! (894 reviews)
Howard Johnson by Wyndham Lenox
Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
HK$727
HK$812 total
7 Sept - 8 Sept
includes taxes & fees
Quality Inn Great Barrington
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA
HK$840
HK$939 total
31 Aug - 1 Sept
includes taxes & fees
Quality Inn Lee - Lenox South
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

1055 South Street Pittsfield MA
HK$934
HK$1,043 total
14 Sept - 15 Sept
includes taxes & fees
9.4/10 Exceptional! (164 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Hideaway Inn Lenox

Hideaway Inn Lenox

11 Old Stockbridge Rd Lenox MA
HK$1,093
HK$1,221 total
7 Sept - 8 Sept
includes taxes & fees
Hideaway Inn Lenox
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
HK$1,240
HK$1,385 total
14 Sept - 15 Sept
includes taxes & fees
The Yankee Inn

Hotels in Sheffield with star-rating

Find out more about Sheffield

Top reasons to visit Sheffield

  • Outdoor Adventures: Sheffield offers thrilling activities like skiing and hiking amidst stunning national parks and serene nature reserves.
  • Charming Local Culture: Discover local art galleries and engage with the rich history of the area, providing a taste of its unique heritage.
  • Family-Friendly Fun: Enjoy apple picking and exciting rides, ensuring a delightful experience for visitors of all ages.
  • Picturesque Accommodations: Stay in charming agritourism properties and inviting bed and breakfasts in a friendly community setting.
  • Scenic Day Trips: Explore nearby attractions for memorable excursions in the picturesque Berkshires.

Find great hotels near Sheffield

Sheffield, Massachusetts, offers a delightful array of accommodation options, including charming agritourism properties and inviting bed and breakfasts. Perfect for families and pet-friendly travellers alike, you can enjoy a memorable vacation experience surrounded by nature. With convenient access to nearby attractions and accommodations in Great Barrington, Sheffield is an ideal destination for those seeking adventure and relaxation in the picturesque Berkshires.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled in the picturesque Berkshires, this 3.5-star resort combines comfort with family-friendly amenities, making it ideal for a fun-filled vacation. Located 19.3km from Sheffield, it offers easy access to skiing activities and other winter sports. The resort boasts an array of facilities tailored for children, including an arcade game room, a shared playground, and onsite mini-golf. With options for relaxing stays or exciting adventures, this resort is perfect for families and business travellers alike, ensuring a memorable experience for all.
  • Quality Inn: Situated a mere 9.7km from Sheffield, Quality Inn caters to the adventurous spirit in every traveller. This accommodation is perfect for those seeking business travel or thrilling outdoor experiences. Guests can indulge in a variety of adventure sports, such as skiing lessons, snowboarding, snow tubing, and hiking or biking nearby. The hotel's focus on recreation ensures that each guest can enjoy both relaxation and excitement during their stay, making it an excellent choice for active visitors.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Located 11.3km from Sheffield, the Holiday Inn Express Hotel & Suites Great Barrington is an inviting choice for business travellers and those seeking an LGBTQIA welcoming environment. This hotel prides itself on inclusivity and comfort, providing essential amenities for a pleasant stay. Its affiliation with LGBTQI travel guides ensures that all guests feel at home, making it a friendly and accommodating option for anyone visiting the area.

Where to stay near Sheffield

Sheffield, Massachusetts, offers a delightful escape for travellers seeking adventure and relaxation amidst the stunning Berkshire surroundings. Explore the charming local history, enjoy beautiful evenings, and soak in the serene scenery. Nearby, you'll find family-friendly activities and romantic spots perfect for couples. The area boasts a range of accommodations, ensuring a pleasant stay in this friendly community. Discover the best of Sheffield and its picturesque surroundings for an unforgettable holiday experience.

  • The Berkshires: Located 17.7km from Sheffield, The Berkshires is a picturesque region known for its stunning landscapes and outdoor adventures. Visitors flock here for a blend of activities such as skiing, hiking, and enjoying the breathtaking scenery throughout the year. The area boasts several ski resorts and fields, making it a winter wonderland during the colder months. With tranquil lakes and majestic mountains, The Berkshires offers an ideal backdrop for both relaxation and exploration, particularly in the summer months when outdoor activities are at their peak.
  • Great Barrington: Just 9.7km from Sheffield, Great Barrington is a vibrant city that attracts outdoor enthusiasts and sports lovers alike. The city experiences a steady influx of visitors year-round, with peaks during the summer months. Known for its excellent skiing opportunities and charming downtown area, Great Barrington features inviting parks and lovely lakes perfect for leisurely strolls. This city captures the essence of adventure, inviting travellers to indulge in a variety of sports and outdoor activities, all while enjoying the natural beauty that surrounds it.
  • Mount Washington: A quaint village situated 8.0km from Sheffield, Mount Washington offers a serene escape for those seeking outdoor experiences. The village showcases remarkable scenery, particularly for hikers and skiers drawn to its natural beauty and adventure opportunities. With its proximity to national state parks and stunning mountain peaks, Mount Washington is perfect for nature lovers. The area sees a consistent flow of visitors, particularly in February and during the summer, making it an excellent destination for those looking to immerse themselves in the great outdoors.

Things to do near Sheffield

Sheffield, Massachusetts, offers a delightful blend of adventure and relaxation, perfect for outdoor enthusiasts. Engage in thrilling activities such as skiing at local resorts, or enjoy a leisurely day of apple picking. Art galleries provide a taste of local culture, while family outings and exciting rides ensure fun for all ages. Don't miss the opportunity to explore nearby attractions on day trips, making Sheffield a charming destination for your vacation.

Shopping

In Sheffield, you can enjoy local shopping experiences at charming stores like Hoffman's Pottery. If you're up for a drive, visit Lee Premium Outlets, located 22.5km away, offering a range of brand-name outlets, or the Berkshire Mountain Country Store, situated 24.1km from Sheffield.

Recreation

Lake Mansfield Park offers a tranquil retreat with picturesque views and serene walking paths, perfect for relaxation and rejuvenation. Music Mountain hosts delightful concerts, providing an entertaining atmosphere to unwind. For outdoor enthusiasts, Undermountain Golf Course delivers a refreshing sporting experience amidst beautiful landscapes.

Adventure

At Ski Butternut, 8.0km from Sheffield, experience exhilarating skiing amidst a vibrant sports atmosphere. Alternatively, the Catamount Ski Area, 12.9km away, offers thrilling slopes for snow enthusiasts. For a scenic adventure, the Housatonic River Walk, 9.7km distant, features picturesque hiking trails surrounded by nature.

Nightlife

Experience the vibrant nightlife in Sheffield by visiting the Mahaiwe Performing Arts Center for live performances, or enjoy a meal and music at Infinity Music Hall and Bistro. For a classic theatre experience, catch a show at the Berkshire Theatre Festival, all offering enchanting cultural vibes.

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

Booking tips and Expedia advantages for Sheffield

For a budget-friendly trip to Sheffield, consider visiting in January or March to April, when accommodation prices are lower. Tuesday is the most economical day to stay, while Saturday tends to be pricier. Use Expedia to find the best hotel deals by sorting prices from lowest to highest. Combining your hotel, flights, and activities into one package can also yield savings. Explore free activities in the area to further enhance your experience without straining your budget.

  • 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: Utilise Expedia’s search tool to refine your choices based on your budget, preferred location, and the type of hotel you desire. To find the most affordable prices and offers, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel booking in Sheffield with your flights and activities through an Expedia package.

Find the best attractions near Sheffield

Sheffield, Massachusetts, offers an ideal destination for adventure and outdoor enthusiasts. With its stunning national parks, serene nature reserves, and picturesque lakes, visitors can indulge in eco-friendly activities and thrilling adventures. Whether you're skiing in the winter or enjoying hiking and exploring the natural beauty during warmer months, Sheffield promises a memorable escape into the great outdoors.

  • Haystack Mountain State Park: Experience breathtaking views and invigorating hikes in this stunning national park. With trails that wind through lush forests and rocky terrains, it’s perfect for outdoor enthusiasts seeking adventure and scenic beauty.
  • Housatonic River: Enjoy leisurely strolls along the banks of the Housatonic River, where the tranquil waters offer a serene backdrop for picnics and nature photography. This picturesque river is ideal for fishing and canoeing, connecting you with the local wilderness.
  • Three Mile Pond Wildlife Management Area: Immerse yourself in the eco-friendly vibes of this nature reserve, perfect for birdwatching and hiking. Discover diverse wildlife while exploring well-maintained trails that showcase the area's natural beauty.

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 can fly into several major airports. ALBany International Airport (ALB) is situated 80.5km away, with notable hotels like the Park Manor Hotel and The Landing Hotel at Rivers Casino & Resort, both 12.9km from the airport. Hartford's Bradley International Airport (BDL) is 59.5km from Sheffield, offering options like the DoubleTree by Hilton Hartford and Simsbury 1820 House, 1.6km and 11.3km away, respectively. Lastly, Stewart International Airport (SWF) in Newburgh, 511.3km from Sheffield, features hotels such as The Dutchess Inn and Spa at Beacon, just 9.7km from the airport.

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 traveller data. This B&B offers free breakfast and free parking. Two other options for your trip to the area are The Yankee Inn and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Sheffield.
What are some of the best holiday rentals that Sheffield has to offer?
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Sheffield is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. 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 reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If your reservation is non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.
What are some accommodation options with pools in Sheffield?
The Yankee Inn: Offers a seasonal outdoor pool, an indoor pool and buffet. Berkshire Mountain Lodge and Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG are a couple of other choices that feature an on-site pool. View all hotels with pools in Sheffield.
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 29 hotels and other accommodation options to choose from. Find out more about Sheffield.
What are the top places to visit in Sheffield?
Favourite places to visit include Housatonic River, Magnolia Bluffs Casino and Three Mile Pond Wildlife Management Area. A couple of additional sights to add to your itinerary are Suter Farm and Mount Everett State Reservation. Take a look at what more there is to see and do in Expedia's Sheffield guide.
What's the seasonal weather like in Sheffield?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Sheffield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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