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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, (45 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is AU$229
includes taxes & fees
28 Apr - 29 Apr
Wilder House Berkshires

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (912 reviews)
"All clean staff great service "
United States
Pedro
The price is AU$160
includes taxes & fees
27 Apr - 28 Apr
Berkshire Mountain Lodge

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (416 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
The price is AU$169
includes taxes & fees
26 Apr - 27 Apr
Locust Tree Bed and Breakfast LLC

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 location, friendly staff"
United States
James
The price is AU$117
includes taxes & fees
26 Apr - 27 Apr
Quality Inn Great Barrington

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, (758 reviews)
"Staff was great! Clean room, parking was always available. Breakfast was great. Had a great time!"
United States
Brigid
The price is AU$173
includes taxes & fees
6 May - 7 May
Holiday Inn Express Hotel & Suites Great Barrington 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, (576 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is AU$117
includes taxes & fees
25 Apr - 26 Apr
Travelodge by Wyndham Great Barrington Berkshires

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (844 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
The price is AU$98
includes taxes & fees
30 Apr - 1 May
Monument Mountain Motel

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (909 reviews)
"Such a cool and affordable place to stay in the Berkshires. Great lobby/bar with a good restaurant."
United States
Kathy
The price is AU$140
includes taxes & fees
12 May - 13 May
Berkshires Untold

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, (778 reviews)
"Staff made our stay enjoyable. Very friendly and extremely helpful. Wanted to check in earlier then normal. They were very helpful. Breakfast was normal chain breakfast. Very quiet hotel."
United States
Graham
The price is AU$237
includes taxes & fees
28 Apr - 29 Apr
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (218 reviews)
"Delightful and well appointed stay! Close to so many things and very cozy."
United States
Jackie
The price is AU$219
includes taxes & fees
26 Apr - 27 Apr
the Alander

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (295 reviews)
"Overall great amenities and great price"
United States
Stacie
The price is AU$374
includes taxes & fees
27 Apr - 28 Apr
Interlaken Inn & Resort

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (218 reviews)
"Very clean. Updated "
United States
jennifer
The price is AU$181
includes taxes & fees
25 Apr - 26 Apr
Chatham Travel Lodge

The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (134 reviews)
"Room was clean"
United States
Patrick
The price is AU$169
includes taxes & fees
27 Apr - 28 Apr
The Brooks Motel

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,001 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is AU$170
includes taxes & fees
26 Apr - 27 Apr
Quality Inn Lee - Lenox South

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (851 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
The price is AU$123
includes taxes & fees
24 Apr - 25 Apr
Howard Johnson by Wyndham Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Very clean, modern hotel. Would definitely stay here again. "
United States
Debra
The price is AU$200
includes taxes & fees
30 Apr - 1 May
Hampton Inn & Suites Berkshires-Lenox

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (173 reviews)
"Best host (Lucas) makes all the difference! Great views and delicious breakfasts. "
United States
diane
The price is AU$230
includes taxes & fees
26 Apr - 27 Apr
Blackberry River 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)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is AU$181
includes taxes & fees
17 May - 18 May
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (158 reviews)
"We stay here frequently…always super clean and the inn keepers are very kind."
United States
Tracy
The price is AU$340
includes taxes & fees
25 Apr - 26 Apr
Cornwall Inn and Lodge

The Whitlock

The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (293 reviews)
"Lovely historical hotel within walking distance to many great shops and restaurants. Staff members maintained good communication and were very helpful throughout our stay. Rooms were clean, quiet, and comfortable. Would definitely stay there again."
United States
Elaine
The price is AU$216
includes taxes & fees
27 Apr - 28 Apr
The Whitlock
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

Recent Reviews in Sheffield

More cheap accommodation in Sheffield

Find out more about Sheffield

Top reasons to visit Sheffield

  • Outdoor Adventures: Sheffield is perfect for skiing and outdoor sports, surrounded by stunning national parks and nature reserves.
  • Art and Culture: Discover vibrant murals and engage with local art galleries, showcasing the town's creative spirit.
  • Charming Town Centre: Enjoy a friendly atmosphere in the town centre, ideal for families and couples alike.
  • Unique Accommodation: Choose from delightful bed and breakfasts and agritourism properties for a memorable stay.
  • Equestrian Experiences: Participate in Clydesdale horse tours for a unique and engaging adventure.

Find great hotels near Sheffield

Sheffield, Massachusetts offers a delightful range of accommodation options, perfect for every traveller. From charming bed and breakfasts to unique agritourism properties, you can find the ideal spot to unwind. Many establishments cater to families and pets, ensuring a warm welcome for all. Whether you're seeking adventure or a peaceful retreat, Sheffield’s best hotels and top accommodations will provide a memorable experience 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 is perfect for families and adventure seekers alike. Located 19.3km from Sheffield, it boasts easy access to skiing and outdoor activities. Guests can enjoy a variety of adventure sports, such as snowboarding, hiking, and tubing, all within a short distance. Families will appreciate the on-site amenities, including a mini-golf course and an arcade game room, ensuring fun for all ages. The resort's welcoming atmosphere makes it an ideal base for those looking to explore the great outdoors.
  • Quality Inn: Situated just 9.7km from Sheffield, Quality Inn caters to both adventure and business travellers. This property offers a range of facilities designed for those on work trips, including a business centre and meeting rooms. For the adventurous, guests can indulge in cross-country skiing and various hiking trails nearby. The hotel’s comfortable accommodations and convenient location make it a practical choice for those needing to balance work with pleasure.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Located 11.3km from Sheffield, this hotel is a welcoming haven for business travellers and the LGBTQIA community. With its affiliation to LGBTQI travel guides, it provides inclusive and supportive services. The hotel features a fully equipped business centre, conference space, and 24-hour business facilities, ensuring that all your work needs are met. Guests can enjoy a comfortable stay with easy access to local attractions, making it a great choice for both business and leisure.

Where to stay near Sheffield

Sheffield, Massachusetts, offers a delightful blend of adventure and relaxation, making it an ideal vacation spot. Explore the charming Sheffield town centre with its friendly atmosphere, perfect for families and couples alike. Enjoy skiing and outdoor sports, or take in the stunning scenery of the surrounding regions. Nearby, you'll find lively cities and quaint neighbourhoods, each with its unique vibe, ensuring a memorable experience for every traveller.

  • The Berkshires: Nestled approximately 17.7km from Sheffield, The Berkshires offers a captivating blend of outdoor adventure and stunning natural scenery. This region is a year-round destination, attracting visitors for its ski fields and resorts in winter, and hiking trails and lakes in warmer months. The landscape is dotted with majestic mountains and serene lakes, making it perfect for both relaxation and adventure. Notable landmarks, including conference venues and scenic spots, enrich the travel experience, ensuring there's something for everyone in this beautiful part of Massachusetts.
  • Great Barrington: Just 9.7km away from Sheffield, Great Barrington is a vibrant city that promises a multifaceted travel experience. Known for its thrilling ski resorts and diverse outdoor sports, this locale is particularly popular from June to August. With its proximity to stunning national state parks and picturesque mountains, it offers an ideal playground for both thrill-seekers and nature enthusiasts. Visitors can enjoy the charming atmosphere of the town, filled with boutique shops and delightful eateries, making it a charming stop on your journey.
  • Ashley Falls: Located a mere 6.4km from Sheffield, Ashley Falls is a quaint city that boasts a welcoming community spirit and a rich array of outdoor activities. This area sees its peak visitor numbers during the summer months and autumn, making it a lively spot for those seeking adventure. The nearby ski fields and parks are perfect for sports enthusiasts, while the local town hall and serene lakes provide a glimpse into the region's charm. Ashley Falls is an excellent choice for those looking to immerse themselves in both nature and local culture.

Things to do near Sheffield

Sheffield, Massachusetts, offers a fantastic blend of adventure and relaxation, making it perfect for a memorable vacation. Enjoy outdoor activities such as skiing at local resorts, exploring art galleries, and taking part in Clydesdale horse tours. With its scenic beauty and numerous attractions, Sheffield is an ideal destination for sports enthusiasts and those seeking a unique experience in the great outdoors.

Shopping

In Sheffield, you can enjoy shopping at local gems. If you're up for a drive, check out Lee Premium Outlets, 22.5km away, featuring a range of brands, or visit the Berkshire Mountain Country Store and Hoffman's Pottery, both located 24.1km from Sheffield for unique finds.

Recreation

At Lake Mansfield Park, immerse yourself in nature with tranquil walking trails and serene picnic spots, perfect for relaxation. Undermountain Golf Course invites you to enjoy a round of golf amidst beautiful landscapes, while Music Mountain offers delightful concerts that blend entertainment with the area's stunning scenery.

Adventure

Ski Butternut, located 8.0km from Sheffield, offers thrilling skiing experiences with a lively atmosphere. For an adrenaline rush, head 12.9km to Catamount Aerial Adventure Park for ziplining among the treetops. Alternatively, enjoy a scenic hike along the Housatonic River Walk, situated 9.7km away, surrounded by nature.

Nightlife

Sheffield's nightlife features the Mahaiwe Performing Arts Center, just 9.7km away, offering a cultural theatre experience. Alternatively, enjoy a meal and live music at Infinity Music Hall and Bistro, 17.7km away, or catch a show at the Berkshire Theatre Festival, 19.3km away, all radiating a vibrant atmosphere.

Booking tips and Expedia advantages for Sheffield

For a budget-friendly trip to Sheffield, Massachusetts, consider visiting in January or March to April, when accommodation prices dip. Tuesdays are the least expensive days to stay, while Saturdays are pricier. Use Expedia’s search tool to find affordable hotels and filter for eco-friendly options. Save even more by bundling your hotel, flights, and activities when booking through Expedia. Look out for great deals and value-for-money offerings to maximise your savings while exploring this charming town.

  • 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 enables you to choose your budget, preferred location, and other criteria. You can arrange your search results to display hotels from the most affordable to the higher-priced options, making it easy to find the best deals. Additionally, you can refine your search by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that you can book.
  • Consider bundling your trip: You can save some dollars by combining your Sheffield hotel booking with your flights and activities through an Expedia package deal.

Find the best attractions in and around Sheffield

Sheffield, Massachusetts, is perfect for a ski or adventure holiday, offering a range of outdoor activities and eco-friendly experiences. Explore the stunning national parks, nature reserves, and engaging museums in the area. Don't miss the vibrant Sheffield murals and local tas, which add a unique touch to your visit. This charming town caters to adventure seekers and culture enthusiasts alike, ensuring a memorable getaway.

  • Bash Bish Falls State Park: Experience the breathtaking beauty of Bash Bish Falls, where cascading waters create a serene backdrop for hiking and exploring nature. The park's rugged terrain and picturesque scenery offer an adventure for outdoor enthusiasts seeking tranquillity and stunning views.
  • Ashley House: Step back in time at the Ashley House, a charming museum that showcases the rich cultural heritage of Sheffield. With its preserved architecture and engaging exhibits, it provides a fascinating glimpse into the local history and the lives of its past residents.
  • Lake Buel: Enjoy a romantic day at Lake Buel, a stunning lake surrounded by lush landscapes. Relax on the beach, indulge in water activities, or simply soak in the peaceful atmosphere while watching the sunset over the water.

Best time to go to Sheffield

The best time to visit Sheffield is dependant 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

When visiting Sheffield, Massachusetts, you can fly into several major airports. Hartford, CT's Bradley International Airport (BDL) is 59.5km away, with nearby hotels such as the 4-star Simsbury 1820 House, located 11.3km from the airport, and the Sheraton Hartford Hotel at Bradley Airport, which is right at the terminal. Albany International Airport (ALB) is another option, situated 80.5km from Sheffield, with excellent hotel choices like the 4-star Landing Hotel at Rivers Casino & Resort and the Park Manor Hotel, both 12.9km away. Lastly, Stewart International Airport (SWF) in Newburgh, NY, is 511.3km away, with hotels such as the 3-star Crossroads Hotel, just 3.2km 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 Berkshire Mountain Lodge and Berkshires Untold. See all available top hotels, or vacation rentals in Sheffield.
What are some of the best holiday rentals that Sheffield has to offer?
Cozy Riverside Berkshires Retreat: This holiday home rental outside of Sheffield is located on a river, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and kitchenware, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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?
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 Red Lion Inn 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 34 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 Mount Everett State Reservation. A couple of additional sights to add to your itinerary are Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary. 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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