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Top hotels and accommodation in Sheffield

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (28)
"Always perfect! "
The price is AU$324
includes taxes & fees
18 Aug - 19 Aug
Wilder House Berkshires

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Beautiful location!"
The price is AU$217
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Wonderful place to stay"
The price is AU$230
includes taxes & fees
8 Sept - 9 Sept
The Yankee, Trademark Collection by Wyndham

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (664)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is AU$275
includes taxes & fees
1 Sept - 2 Sept
Berkshires Untold

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

3.5 star property
9.0 out of 10, Wonderful, (687)
"Had a great time"
The price is AU$188
includes taxes & fees
8 Sept - 9 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is AU$279
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (509)
"Property was excellent "
The price is AU$261
includes taxes & fees
2 Sept - 3 Sept
The Constance by the Lenox Collection

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"Loved our visit"
The price is AU$381
includes taxes & fees
13 Aug - 14 Aug
The Red Lion Inn

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (546)
"Excellent stay!"
Berkshire Mountain Lodge

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.4 out of 10, Exceptional, (12)
"Really enjoyed my stay here, definitely need a car to get around"
The price is AU$261
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

the Alander

2.5 star property
9.0 out of 10, Wonderful, (152)
"Beautiful area. Quiet, peaceful and nicely appointed room. Dinner at the restaurant was excellent. "
The price is AU$275
includes taxes & fees
24 Aug - 25 Aug
the Alander

The Brooks Motel

2.0 star property
7.6 out of 10, Good, (93)
"Basic, clean and good value for the money."
The price is AU$241
includes taxes & fees
20 Aug - 21 Aug
The Brooks Motel

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (622)
"It was lovely!"
The price is AU$109
includes taxes & fees
24 Aug - 25 Aug
Econo Lodge Lee - Great Barrington

The Whitlock

2.0 star property
8.6 out of 10, Excellent, (261)
"Lovely hotel in the heart of Lenox. The rooms and property were very nice. The staff was great. We would definitely stay here again!"
The price is AU$301
includes taxes & fees
2 Sept - 3 Sept
The Whitlock

The Dewey

3.5 star property
8.8 out of 10, Excellent, (320)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is AU$298
includes taxes & fees
3 Sept - 4 Sept
The Dewey

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (724)
"Was the perfect stop over for our way home. All the employees were extremely friendly. "
The price is AU$259
includes taxes & fees
25 Aug - 26 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Chatham Travel Lodge

2.5 star property
7.8 out of 10, Good, (188)
"Nice and quiet"
The price is AU$199
includes taxes & fees
10 Aug - 11 Aug
Chatham Travel Lodge

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (123)
"We had a vey clean room with a comfortable bed The breakfast was awesome as was the entire staff. Enjoyed our stay"
The price is AU$290
includes taxes & fees
2 Sept - 3 Sept
Blackberry River Inn

Prospect Berkshires

2.0 star property
9.0 out of 10, Wonderful, (2)
"So fantastic!! The cabins are gorgeous and very well appointed. We are going back!"
The price is AU$706
includes taxes & fees
10 Aug - 11 Aug
Prospect Berkshires

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (398)
"Nice property! a little dated but overall great for 1 night"
The price is AU$185
includes taxes & fees
10 Aug - 11 Aug
Locust Tree Bed and Breakfast LLC
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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Learn more about Sheffield

Love casinos and history? Get away to Sheffield!

Top Sheffield Hotel Reviews

Find out more about 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.

*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, 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?

Antique Farmhouse Totally Restored : This highly rated holiday home rental in Sheffield is located in a rural location, 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. 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 35 hotels and other accommodation options to choose from. Find out more about Sheffield.

What are the top places to visit in Sheffield?

The picturesque setting of Housatonic River and Mount Everett State Reservation exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Magnolia Bluffs Casino and Thom Reed UFO Monument Park. 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.