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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)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is £148
includes taxes & fees
9 Mar - 10 Mar
Wilder House Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (19 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is £115
includes taxes & fees
3 Mar - 4 Mar
Element Lenox Berkshires

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, (739 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is £85
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (824 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,005 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is £72
includes taxes & fees
10 Mar - 11 Mar
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, (834 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
The price is £57
includes taxes & fees
26 Feb - 27 Feb
Howard Johnson by Wyndham 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, (415 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is £89
includes taxes & fees
26 Feb - 27 Feb
Locust Tree Bed and Breakfast LLC

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is £48
includes taxes & fees
26 Feb - 27 Feb
Pleasant Valley Motel West Stockbridge

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,017 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is £77
includes taxes & fees
4 Mar - 5 Mar
The Yankee, Trademark Collection by Wyndham

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.2 out of 10, Very good, (16 reviews)
"Antonia was wonderful and made our stay special. She was kind and warm and when we were initially unhappy with our room immediately rectified the situation and in the end our stay was perfect! It’s a charming hotel, clean and centrally located, walking distance to all the local shops in town."
United States
Jamie
The price is £127
includes taxes & fees
16 Mar - 17 Mar
The Millerton Inn

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (864 reviews)
"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "
United States
Melissa
Berkshires Untold

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (572 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is £62
includes taxes & fees
26 Feb - 27 Feb
Travelodge by Wyndham Great Barrington Berkshires

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, (83 reviews)
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
The price is £109
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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)
"Clean room, nice staff , decent breakfast. Overall a good stay . "
United States
Anindita
The price is £81
includes taxes & fees
17 Mar - 18 Mar
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, (1,000 reviews)
"Clean room, great location"
United States
Andrea
The price is £55
includes taxes & fees
23 Mar - 24 Mar
Quality Inn Great Barrington

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (863 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is £111
includes taxes & fees
26 Feb - 27 Feb
Berkshire Mountain Lodge

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 £76
includes taxes & fees
4 Mar - 5 Mar
Shaker Mill Inn

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (554 reviews)
"Great friendly staff"
United States
Pablo
The price is £91
includes taxes & fees
26 Feb - 27 Feb
The Little Lion

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
The price is £166
includes taxes & fees
26 Feb - 27 Feb
The Berkshire Mountain Inn

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (38 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is £98
includes taxes & fees
20 Mar - 21 Mar
East Rock 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 Adventure: Sheffield is perfect for skiing and outdoor sports, offering thrilling activities for adventure enthusiasts.
  • Picturesque Landscapes: Enjoy stunning scenery and charming surroundings, ideal for family outings or romantic getaways.
  • Welcoming Community: Experience the friendly atmosphere of downtown Sheffield, enhanced by the warmth of the locals.
  • Cultural Attractions: Discover engaging museums and local history, showcasing Sheffield's unique heritage.
  • Diverse Accommodation: Choose from cosy bed and breakfasts to unique agritourism stays, catering to all travellers.

Find great hotels near Sheffield

Sheffield, Massachusetts, offers a charming selection of accommodation options to suit every traveller's needs. From inviting bed and breakfasts to unique agritourism properties, you'll find the perfect place to unwind. Many hotels cater to families and pet owners, ensuring a comfortable stay for all. Whether you're seeking adventure or a peaceful retreat, Sheffield's hospitality awaits you with a variety of choices to enhance your visit.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled 7.5km from Sheffield, this 3.5-star resort is perfect for families seeking a memorable getaway. The resort's family-friendly atmosphere is complemented by a variety of amenities including a mini-golf course, playground, and arcade game room. Business travellers will appreciate the dedicated business centre, ensuring productivity during their stay. With free cribs available for younger guests, this resort strikes an ideal balance between leisure and convenience for families.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Located a mere 4.3km from Sheffield, this hotel welcomes both business travellers and LGBTQIA guests with open arms. The modern facilities include a 24-hour business centre, meeting rooms, and conference space, making it an excellent choice for corporate visits. Guests can enjoy a comfortable stay with convenient access to nearby attractions while benefiting from the hotel's inclusive environment.
  • Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires: Also situated 4.3km from Sheffield, this hotel caters to adventure seekers and business travellers alike. Guests can engage in a range of outdoor activities, from mountain biking to skiing, all available nearby. The hotel features accessible business amenities, including meeting rooms and a business centre. With its welcoming atmosphere for LGBTQIA guests, this accommodation offers a perfect blend of excitement and professionalism.

Where to stay near Sheffield

Sheffield, Massachusetts, offers a delightful blend of adventure and history, perfect for your vacation. Explore the charming downtown, where friendly locals enhance the inviting atmosphere. Enjoy stunning scenery in the surrounding areas, ideal for family-friendly outings or romantic getaways. Whether you’re skiing or simply soaking in the beautiful vibes, Sheffield promises a memorable experience for every traveller. Don’t miss the chance to discover the unique charm of this picturesque town and its surroundings.

  • The Berkshires: Nestled 6.8km away from Sheffield, The Berkshires is a picturesque region known for its stunning outdoor landscapes and vibrant arts scene. Travellers flock here for adventure, particularly during the summer months from June to August, when the area buzzes with activity. The Berkshires offers a range of outdoor experiences including skiing in winter and exploring beautiful lakes and mountains year-round. With its charming ski resorts and event venues, it’s an ideal spot for those seeking both relaxation and excitement amidst nature's beauty.
  • Great Barrington: Located a mere 3.7km from Sheffield, Great Barrington is a lively city that attracts visitors throughout the year. Known for its ski fields and adventurous spirit, the peak season is during the summer months of June to August, although the charming town remains inviting in the cooler months as well. The area is surrounded by natural wonders, including lakes and mountains, and is complemented by the nearby national state park, offering a perfect blend of sports and outdoor activities for every traveller.
  • Ashley Falls: Just 2.5km from Sheffield, Ashley Falls is an inviting city that offers a quintessential New England experience. The town draws visitors year-round, with peak arrivals during the summer and autumn months. Known for its adventurous spirit, Ashley Falls is perfect for outdoor enthusiasts, featuring access to ski fields and resorts. Visitors can enjoy the serene lakes and local parks, making it an excellent choice for those seeking both adventure and a peaceful retreat in nature.

Things to do near Sheffield

Sheffield, Massachusetts, is an ideal destination for those seeking adventure and outdoor sports. Visitors can enjoy a variety of activities, including skiing at the local ski fields and resorts. With its picturesque landscapes and recreational opportunities, Sheffield offers an exciting getaway for ski enthusiasts and adventure seekers alike.

Shopping

For a delightful shopping experience in Sheffield, visit the local boutiques and charming shops. If you're up for a drive, Lee Premium Outlets, located 8.7km away, offers a range of brand-name discounts, while the Berkshire Mountain Country Store and Hoffman's Pottery, both 9.3km away, provide unique gifts and souvenirs.

Recreation

Experience tranquility at Lake Mansfield Park, where you can unwind amidst nature and enjoy leisurely walks. For an active day, head to Undermountain Golf Course for a round of golf surrounded by beautiful landscapes. Conclude your day with live performances at Music Mountain, embracing the vibrant arts scene.

Adventure

Catamount Ski Area offers thrilling winter sports with stunning views, located 5.0km from Sheffield. For motorsport enthusiasts, Lime Rock Park, 8.1km away, provides an exhilarating racing experience. Meanwhile, the Housatonic River Walk, 3.7km from Sheffield, invites you to enjoy scenic hikes amidst nature's beauty.

Nightlife

For a delightful evening in Sheffield, consider catching a show at the Mahaiwe Performing Arts Center, just 3.7km away, or enjoy a meal and music at Infinity Music Hall and Bistro, 6.8km from town. The Berkshire Theatre Festival, 7.5km away, also promises captivating performances.

Booking tips and Expedia advantages for Sheffield

To save money during your visit to Sheffield, Massachusetts, consider travelling in January or March to April when accommodation prices are lower. Booking your stay on a Tuesday can also help reduce costs, as Saturdays tend to be the most expensive. Use Expedia's search tool to find budget-friendly options, and consider eco-certified hotels for added savings. Additionally, look for package deals that combine flights, hotels, and activities to maximise your budget. Enjoy free outdoor activities in the area to make the most of your trip without breaking the bank.

  • 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 tailor your options based on your budget, preferred location, and the type of hotel you desire. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are currently available. To find the best prices and offers, sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by booking an Expedia package that combines your hotel stay in Sheffield with your flights and activities.

Find the best attractions in and around Sheffield

Sheffield, Massachusetts, offers a delightful blend of outdoor adventure and eco-friendly experiences, making it perfect for skiing and sports holidays. Visitors can explore local attractions like the nearby state parks and nature reserves, as well as engaging museums that showcase the area’s history. Whether you're seeking Sheffield’s unique attractions or nearby points of interest, there’s plenty to discover for nature enthusiasts and adventure seekers alike.

  • Mount Frissell: Experience the stunning vistas at Mount Frissell, the highest peak in Massachusetts, located 6.2km from Sheffield. Ideal for hiking enthusiasts, it offers breathtaking scenery and a chance to connect with nature.
  • Bash Bish Falls State Park: A mere 4.3km from Sheffield, this park boasts the majestic Bash Bish Falls, perfect for adventure seekers. Enjoy hiking trails that lead you through lush landscapes and picturesque views, making it a perfect outdoor getaway.
  • Ashley House: Located within Sheffield, the Ashley House is a charming museum that showcases local history and culture. Step back in time and explore the rich heritage of the region through its fascinating exhibits.

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 CloudyAverageAverage
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 LowSlightly Low
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 nearby airports. Hartford, CT (BDL-Bradley Intl.) is situated 23.0km away, with hotel options like the DoubleTree by Hilton Hartford - Bradley Airport, just 621m from the airport. Newburgh, NY (SWF-Stewart Intl.) is 35.4km from Sheffield, where you can stay at The Dutchess Inn and Spa at Beacon, located 3.7km from the airport. Albany, NY (ALB-Albany Intl.) is 31.1km away, offering accommodations such as The Landing Hotel at Rivers Casino & Resort, which is 5.0km from the airport. Each airport provides convenient access to Sheffield via nearby hotels and transport services.

Frequently asked questions

What is the best area to stay in Sheffield?
The best area to stay in Sheffield, Massachusetts, is the town centre, particularly around Main Street (Route 7).

Sheffield's town centre is a pleasant and convenient base for exploring the Southern Berkshires. Main Street is where you'll find a selection of antique shops, local eateries, and a few small galleries. The town maintains a relaxed, rural character, making it easy to unwind.

Couples looking for a tranquil getaway will appreciate the quiet charm of Sheffield. Many accommodations here offer a peaceful setting, often with views of the surrounding hills, great for relaxing after a day of exploring the region's art and nature. It's also a great base for visiting nearby towns such as Great Barrington.

For those interested in outdoor activities and nature, staying in or just outside the town centre provides easy access to local hiking trails and scenic drives.
What are the best hotels in Sheffield that travellers recommend?
For a highly recommended hotel in Sheffield, Massachusetts, consider the Wilder House Berkshires.

The Wilder House Berkshires, with an outstanding 9.8 rating, is praised by guests for its comfortable and clean rooms. Travellers particularly enjoy the great and delicious complimentary cooked breakfast. The hotel also offers premium bedding, air conditioning, and free self-parking, ensuring a convenient and pleasant stay.
What are the best family hotels in Sheffield?
For families travelling to Sheffield, the Wilder House Berkshires is an excellent choice.

This highly-rated accommodation, with an impressive 9.8 review score, offers a welcoming stay for families. Guests consistently praise the comfortable and clean rooms, ensuring a pleasant environment for everyone. A significant advantage for families is the complimentary breakfast, including cooked options, which guests describe as great and delicious. Free toiletries, free WiFi, and free self-parking add to the convenience and value. The availability of a free crib further highlights its family-friendly focus, making it easier for parents travelling with infants.
What hotels in Sheffield offer free breakfast?
For hotels in Sheffield that provide complimentary breakfast, the Wilder House Berkshires is an excellent option.

This highly-rated property, with an impressive 9.8 review score, offers both free breakfast and free cooked breakfast, which guests consistently describe as great and delicious. The rooms are noted for being comfortable and clean, and the hotel also provides free WiFi, free self-parking, and premium bedding. Additionally, it is conveniently located just 10.2 km from the Housatonic River.
What are the best budget hotels in Sheffield?
For a great budget hotel in Sheffield, consider the Wilder House Berkshires.

The Wilder House Berkshires has an exceptional review rating of 9.8. Guests consistently mention the comfortable and clean rooms, along with the great and delicious breakfast. This hotel provides a range of complimentary amenities, including free cooked breakfast, free toiletries, free WiFi, and free self-parking. The rooms also feature premium bedding and air conditioning for added comfort. It is located approximately 10.2 km from the Housatonic River.
When is the best time to go to Sheffield?
The best time to visit Sheffield, Massachusetts, depends on your preferences for outdoor activities and the region's natural beauty.

For those who enjoy warm weather and outdoor adventures, the summer months from June to August are ideal. The Berkshires are lush and green during this period, superb for hiking, cycling, and enjoying the numerous lakes and rivers. You'll find many local farms offering fresh produce, and outdoor events are plentiful.

If you're particularly interested in the stunning autumn foliage, late September through October is the most picturesque time to visit. The hillsides transform into a spectacular display of reds, oranges, and yellows, making it superb for scenic drives and photography. This period is very popular, so booking accommodation well in advance is recommended.

For winter sports enthusiasts, December through March offers opportunities for skiing, snowboarding, and snowshoeing at nearby resorts. The landscape is often covered in snow, creating a serene and beautiful setting, though some smaller shops and attractions might have reduced hours.

Spring, from April to May, sees the awakening of the landscape with blooming flowers and budding trees.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Sheffield.
How can I save on a Sheffield hotel booking with Expedia?
Members always get our best prices. Find our best Sheffield hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Sheffield hotel?
Prices for hotels in Sheffield often vary, but you can find a great deal from £55 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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