Sheffield Hotels

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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, (44 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is P9,693
P10,827 total
includes taxes & fees
Apr 7 - Apr 8
Wilder House Berkshires

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (838 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
The price is P3,605
P4,027 total
includes taxes & fees
Apr 8 - Apr 9
Monument Mountain Motel

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (888 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is P5,551
P6,201 total
includes taxes & fees
Apr 8 - Apr 9
Berkshires Untold

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 P6,566
P7,202 total
includes taxes & fees
Apr 9 - Apr 10
Shaker Mill Inn

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,002 reviews)
"Great location, friendly staff"
United States
James
The price is P4,045
P4,518 total
includes taxes & fees
Apr 22 - Apr 23
Quality Inn Great Barrington

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is P8,613
P9,621 total
includes taxes & fees
Apr 13 - Apr 14
Element Lenox Berkshires

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (895 reviews)
"Overall pleasant stay; great facilities, staff, and location"
United States
Casey
The price is P5,218
P7,174 total
includes taxes & fees
May 6 - May 7
Berkshire Mountain Lodge

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,002 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is P4,283
P4,698 total
includes taxes & fees
Apr 7 - Apr 8
Pleasant Valley Motel West Stockbridge

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, (1,003 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is P6,202
P6,927 total
includes taxes & fees
Apr 20 - Apr 21
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (555 reviews)
"Clean … check in , good location for us .. we’ll be back in Maynn"
United States
Kathleen
The price is P6,626
P7,401 total
includes taxes & fees
Apr 8 - Apr 9
The Little Lion

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (574 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is P4,518
P5,046 total
includes taxes & fees
Apr 7 - Apr 8
Travelodge by Wyndham Great Barrington Berkshires

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (843 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
The price is P4,758
P5,315 total
includes taxes & fees
Apr 7 - Apr 8
Howard Johnson by Wyndham Lenox

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
The price is P7,987
P8,922 total
includes taxes & fees
Apr 7 - Apr 8
Hideaway Inn Lenox

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)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is P6,325
P7,273 total
includes taxes & fees
Apr 8 - Apr 9
Locust Tree Bed and Breakfast LLC

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)
"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 P6,093
P6,806 total
includes taxes & fees
Apr 20 - Apr 21
Quality Inn Lee - Lenox South

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)
"New hotel clean and nice. Heated pool and hot tub a bonus. Timely breakfast for early departures- great on demand coffee. Added bonus they have a car charger."
United States
Charline
The price is P7,349
P8,208 total
includes taxes & fees
Apr 13 - Apr 14
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Whitlock

The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (292 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 P5,878
P6,565 total
includes taxes & fees
Apr 8 - Apr 9
The Whitlock

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (214 reviews)
"Delightful and well appointed stay! Close to so many things and very cozy."
United States
Jackie
The price is P8,433
P9,445 total
includes taxes & fees
Apr 7 - Apr 8
the Alander

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (97 reviews)
"Very cosy and friendly "
United States
Dominic
The price is P10,481
P11,707 total
includes taxes & fees
Apr 7 - Apr 8
Granville House

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.6 out of 10, Exceptional, (5 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is P12,047
P13,456 total
includes taxes & fees
Apr 7 - Apr 8
The Berkshire Mountain Inn
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

Find out more about Sheffield

Top reasons to visit Sheffield

  • Outdoor Adventures: Sheffield offers a wealth of activities for nature lovers, including skiing, hiking in national parks, and exploring serene lakes.
  • Scenic Beauty: The town is renowned for its picturesque landscapes, making it a perfect spot for relaxation and photography.
  • Charming Accommodation: Enjoy a variety of delightful lodgings, from cosy Bed & Breakfasts to unique Agritourism properties.
  • Rich Local Culture: Engage with friendly locals and experience the unique charm of this quaint New England town.
  • Wellness Options: Unwind at nearby spas, ensuring a perfect balance of adventure and relaxation.

Find great hotels near Sheffield

Experience the charm of Sheffield, Massachusetts, with a range of delightful accommodation options tailored for every traveller. From inviting Bed & Breakfasts to unique Agritourism properties, Sheffield offers a variety of pet-friendly lodgings perfect for family vacations and adventurous getaways. Whether you're searching for the best hotels or reading reviews, you're sure to find the perfect place to unwind in this picturesque New England town.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Embrace a family-friendly retreat at this welcoming resort, nestled 19.3km from Sheffield. Ideal for families and LGBTQIA travellers, the resort offers a plethora of amenities designed to entertain guests of all ages. With features such as an onsite mini-golf course, a shared playground, and a free crib service, families will find everything they need for a memorable holiday. The arcade game room adds an extra layer of excitement, making it a perfect choice for those looking to create lasting memories together.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Located a mere 11.3km from Sheffield, this hotel caters to business travellers and those seeking an LGBTQIA-friendly environment. The modern accommodations are designed to provide a comfortable stay, with a focus on convenience and efficiency. Guests will appreciate the hotel’s amenities, which include a well-equipped business centre and complimentary breakfast options to kick-start your day. The central location makes it easy to explore the vibrant surroundings while returning to a welcoming atmosphere at the end of the day.
  • The Red Lion Inn: Situated 19.3km from Sheffield, The Red Lion Inn offers a unique blend of adventure and comfort, making it a perfect choice for pet-friendly and business travellers alike. This charming inn is surrounded by breathtaking nature, with activities such as snowshoeing, skiing, and hiking available nearby. With a pet-friendly policy that allows certain pets on-site, guests can enjoy their adventure holidays without leaving their furry companions behind. The inn’s rustic charm and convenient amenities create an inviting atmosphere for all types of travellers.

Where to stay near Sheffield

Sheffield, Massachusetts, offers an enchanting blend of adventure and history, making it an ideal getaway for those seeking outdoor escapades. Explore the picturesque scenery and family-friendly atmosphere while indulging in local charm. Nearby attractions provide opportunities for relaxation and romance, ensuring every traveller finds their perfect experience. With various Sheffield vacation packages available, you can easily discover the best places to unwind and connect with friendly locals during your stay.

  • The Berkshires: Nestled approximately 17.7km from Sheffield, The Berkshires is a stunning region renowned for its breathtaking outdoor experiences and adventure opportunities. This area offers a year-round allure, though visitor numbers peak during the summer months. Outdoor enthusiasts can indulge in skiing during winter, while the picturesque landscapes are perfect for hiking and exploring in warmer months. Local landmarks such as serene lakes and majestic mountains enhance the experience, making it a prime destination for nature lovers and those seeking tranquillity amidst stunning scenery.
  • Great Barrington: Located a mere 9.7km from Sheffield, Great Barrington is a vibrant city that attracts visitors with its thrilling ski and adventure offerings. Known for its sports activities, this city sees a surge in tourists during the summer, making it a great spot for those eager to embrace the great outdoors. With easy access to ski fields and resorts, as well as nearby lakes and parks, Great Barrington promises an exhilarating experience whether you're gliding down the slopes or enjoying a leisurely day in nature.
  • Ashley Falls: Just 6.4km from Sheffield, Ashley Falls is a charming city that offers a mix of adventures and sports, appealing to those with a thirst for outdoor excitement. Visitor numbers peak during the summer months, particularly in July and August. The area is well-known for its skiing, motor racing, and access to national parks, making it a thrilling destination for active travellers. With local attractions including lakes and stadiums, Ashley Falls provides a diverse array of experiences that cater to all adventurers.

Things to do near Sheffield

Sheffield, Massachusetts, is an ideal destination for adventure enthusiasts, offering a range of outdoor activities including skiing at local resorts and exploring scenic parks. Visitors can also indulge in relaxation at nearby spas. With its beautiful landscapes and recreational options, Sheffield promises an enjoyable getaway for those seeking both excitement and tranquility.

Shopping

In Sheffield, you can enjoy quaint shopping experiences at local stores. If you're up for a drive, visit Lee Premium Outlets, 22.5km away, for a variety of brands, or explore the Berkshire Mountain Country Store and Hoffman's Pottery, both located 24.1km from Sheffield.

Recreation

At Lake Mansfield Park, immerse yourself in nature with serene walks and peaceful picnics, perfect for relaxation. Music Mountain offers delightful concerts, providing a vibrant atmosphere to enjoy live performances. For sports enthusiasts, Undermountain Golf Course presents a scenic outdoor setting for a refreshing round of golf.

Adventure

Experience the thrill of skiing at Ski Butternut, a vibrant ski field located 8.0km from Sheffield, perfect for winter sports enthusiasts. Explore the Housatonic River Walk, a picturesque hiking trail 9.7km away, showcasing stunning outdoor scenery. For an exhilarating challenge, visit Catamount Aerial Adventure Park, an exciting zipline ropes course situated 12.9km from Sheffield.

Nightlife

In Sheffield, the Mahaiwe Performing Arts Center offers a charming atmosphere with a variety of shows, just 9.7km away. For a delightful night out, the Infinity Music Hall and Bistro, 17.7km distant, combines exquisite dining with live performances. The Berkshire Theatre Festival, 19.3km away, provides a cultural experience not to be missed.

*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, Massachusetts, consider visiting during the cheaper months of January or March to April, and aim to book your stay on a Tuesday for the best rates. Use Expedia to compare prices and filter for eco-certified hotels to find affordable, sustainable options. Enhance your savings further by bundling your hotel with flights and activities. Additionally, explore free local attractions and utilise public transport for budget-friendly travel around the area.

  • 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 preferences, such as your budget, desired location, and the type of hotel you prefer. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels currently available. To find the most affordable prices and offers, simply sort the price filter from low to high.
  • Consider bundling your trip: You can save money by booking your Sheffield hotel along with your flights and activities through an Expedia package.

Find the best attractions near Sheffield

Sheffield, Massachusetts, is a haven for adventure enthusiasts and outdoor lovers, offering a plethora of activities such as skiing and exploring national parks, nature reserves, and picturesque lakes. The area's attractions provide eco-friendly experiences perfect for travellers seeking a connection with nature. For a comfortable stay, consider hotels near the Sheffield Botanical Gardens, ensuring easy access to the town's natural beauty and outdoor adventures.

  • Great Barrington Historical Society & Museum: Immerse yourself in the rich heritage of the region at this charming museum, located 8.0km from Sheffield. Delve into fascinating exhibits that showcase the local history and culture, providing a glimpse into the past of Great Barrington.
  • Lion's Head Peak: Experience the thrill of adventure at this stunning mountain, situated 12.9km away. Offering breathtaking views and invigorating hikes, Lion's Head Peak is perfect for outdoor enthusiasts seeking scenic beauty and an adrenaline rush.
  • Bash Bish Falls State Park: Just 11.3km from Sheffield, this national park is home to the spectacular Bash Bish Falls. Enjoy the stunning natural scenery, hiking trails, and the refreshing sound of cascading water, making it an ideal spot for nature lovers and adventurers alike.

Best time to go to Sheffield

The best time to visit Sheffield can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Sheffield falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Sheffield falls in January, 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

Sheffield, Massachusetts, is conveniently accessible via several major airports. Hartford, CT (BDL-Bradley Intl.) is approximately 59.5km away, with notable hotels like Simsbury 1820 House, a 4-star bed & breakfast 11.3km from the airport, and Marriott Hartford Downtown, also a 4-star hotel, located 19.3km away. Albany, NY (ALB-Albany Intl.) is around 80.5km distant, with options such as The Landing Hotel at Rivers Casino & Resort and DoubleTree by Hilton Schenectady Downtown, both 12.9km from the airport. Lastly, Newburgh, NY (SWF-Stewart Intl.) is 511.3km away, featuring The Dutchess Inn and Spa at Beacon, located 9.7km from the airport, with various transportation services available.

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.
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'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, Magnolia Bluffs Casino, 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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