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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 NZ$335
includes taxes & fees
8 Mar - 9 Mar
Wilder House Berkshires

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 NZ$202
includes taxes & fees
22 Feb - 23 Feb
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, (1,004 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is NZ$166
includes taxes & fees
9 Mar - 10 Mar
Quality Inn Lee - Lenox South

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 NZ$260
includes taxes & fees
2 Mar - 3 Mar
Element Lenox Berkshires

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

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, (736 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is NZ$193
includes taxes & fees
8 Mar - 9 Mar
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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 NZ$129
includes taxes & fees
23 Feb - 24 Feb
Howard Johnson by Wyndham Lenox

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,009 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is NZ$173
includes taxes & fees
2 Mar - 3 Mar
The Yankee, Trademark Collection by Wyndham

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 NZ$183
includes taxes & fees
15 Mar - 16 Mar
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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 NZ$107
includes taxes & fees
24 Feb - 25 Feb
Pleasant Valley Motel West Stockbridge

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
"owners was nice, room was clean"
United States
tom
The price is NZ$178
includes taxes & fees
22 Feb - 23 Feb
Sunset Inn

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 NZ$171
includes taxes & fees
4 Mar - 5 Mar
Shaker Mill Inn

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1,004 reviews)
"Clean room, great location"
United States
Andrea
The price is NZ$124
includes taxes & fees
24 Mar - 25 Mar
Quality Inn Great Barrington

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (571 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is NZ$140
includes taxes & fees
23 Feb - 24 Feb
Travelodge by Wyndham Great Barrington Berkshires

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (862 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

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 NZ$247
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (850 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is NZ$250
includes taxes & fees
23 Feb - 24 Feb
Berkshire Mountain Lodge

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (168 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is NZ$288
includes taxes & fees
22 Feb - 23 Feb
Blackberry River Inn

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (553 reviews)
"Great friendly staff"
United States
Pablo
The price is NZ$206
includes taxes & fees
23 Feb - 24 Feb
The Little Lion

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (216 reviews)
"Great friendly personable person at the front desk!!"
United States
Carolyn
The price is NZ$217
includes taxes & fees
22 Feb - 23 Feb
Chatham Travel Lodge
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 accommodation in Sheffield

Find out more about Sheffield

Top reasons to visit Sheffield

  • Adventure Activities: Sheffield is a haven for adventure lovers, offering skiing, ice skating, and a range of outdoor sports amidst stunning natural landscapes.
  • Charming Community: Explore the welcoming Sheffield Centre, where friendly locals and scenic beauty create a relaxing atmosphere.
  • Unique Accommodations: Enjoy a variety of delightful stays, from quaint bed and breakfasts to unique agritourism properties, catering to all travellers.
  • Eco-Friendly Experiences: With national parks and nature reserves, Sheffield is perfect for those seeking eco-conscious adventures.
  • Vibrant Pub Scene: Unwind in the local pubs, experiencing the lively atmosphere and community spirit of Sheffield.

Find great hotels near Sheffield

Discover the charm of Sheffield, Massachusetts, with a variety of delightful accommodation options tailored to suit every traveller. From quaint bed and breakfasts to unique agritourism properties, you'll find the perfect spot for a pleasant stay. Enjoy family-friendly amenities, pet-friendly options, and the opportunity for adventure in this picturesque town. Experience the best of Sheffield's hospitality and make your trip truly memorable.

  • 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 LGBTQIA travellers seeking an adventurous getaway. With easy access to ski shuttles and lifts, it’s an ideal base for winter sports enthusiasts. Kids will love the on-site amenities, including an Arcade Game Room, a shared playground, and mini-golf. This resort is designed to cater for a fun-filled family vacation while also offering a welcoming environment for all guests.
  • Quality Inn: Located a mere 9.7km from Sheffield, Quality Inn is tailored for business travellers and adventure seekers alike. With a focus on facilitating work-related needs, the hotel features essential business amenities, making it easy to stay productive while away. For those looking to get their adrenaline pumping, the surrounding area offers a range of adventure sports including downhill skiing, snowboarding, and snow tubing. This hotel provides a balanced mix of work and play for the modern traveller.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Situated 11.3km from Sheffield, this hotel is a great choice for LGBTQIA-friendly business travellers. With a well-equipped 24-hour business centre and meeting spaces, it's designed to meet the needs of professionals on the go. After a day of meetings, unwind in the comfortable rooms that offer modern amenities. Guests appreciate the convenient location and the welcoming atmosphere, ensuring a pleasant stay whether for work or leisure.

Where to stay near Sheffield

Sheffield, Massachusetts, offers a delightful blend of adventure and history, making it an ideal destination for Kiwis seeking a unique getaway. Explore the charming Sheffield Centre, where friendly locals and picturesque scenery create a relaxing atmosphere. Enjoy short stays in comfortable accommodations, perfect for families or romantic retreats. Nearby attractions provide ample opportunities for skiing and outdoor sports, ensuring an unforgettable experience in this stunning region of the USA.

  • Great Barrington: Nestled just 9.7km from Sheffield, Great Barrington is a vibrant city that beckons adventure enthusiasts year-round. With a peak in visitors during the summer months, particularly from June to August, this destination is renowned for its skiing and outdoor sports. The local landscape is dotted with scenic lakes and majestic mountains, making it ideal for both winter sports and summer hiking. Don’t miss the chance to explore the nearby national state parks, where nature’s beauty is on full display, providing endless opportunities for outdoor activities and relaxation.
  • The Berkshires: Located 17.7km from Sheffield, The Berkshires is an enchanting region celebrated for its stunning scenery and outdoor adventures. Visitor numbers tend to peak during the summer months, especially from June to August, as travellers flock here to experience the breathtaking landscapes and recreational opportunities. This area is perfect for those seeking skiing and other outdoor pursuits, with numerous ski resorts and fields available. The Berkshires also features picturesque lakes and mountains, as well as unique event venues that host a variety of cultural events, making it a lively spot for both relaxation and entertainment.
  • Ashley Falls: Just 6.4km from Sheffield, Ashley Falls is a charming city that offers a delightful experience for those looking for adventure. With a moderate seasonal visitor pattern, the peak months of July to August and October draw in travellers eager to enjoy skiing and outdoor sports. The area is home to beautiful lakes and a quaint town hall, alongside lovely parks that provide a serene atmosphere for relaxation. Whether you're hitting the slopes or exploring the local charm, Ashley Falls is a perfect spot for a memorable getaway.

Things to do near Sheffield

Sheffield offers a fantastic range of activities for adventure enthusiasts, including skiing at its popular ski resorts and fields. Visitors can also explore the local area, enjoy the vibrant pub scene, and partake in ice skating. Whether you're seeking thrilling outdoor experiences or a relaxed atmosphere, Sheffield has something for everyone, making it an ideal destination for a memorable holiday.

Shopping

In Sheffield, you can enjoy local shopping at quaint stores like Hoffman's Pottery. If you're up for a drive, visit Lee Premium Outlets, 22.5km away, for a range of brand-name outlets and family-friendly entertainment, or the Berkshire Mountain Country Store, 24.1km away, for unique gifts.

Recreation

Lake Mansfield Park offers a tranquil retreat with scenic views and walking trails, perfect for relaxation. Undermountain Golf Course invites you to enjoy outdoor sports in a picturesque setting, while Music Mountain presents vibrant concerts that bring entertainment and joy to your visit.

Adventure

Experience thrilling skiing at Ski Butternut, located 8.0km from Sheffield, offering fantastic snow sports vibes. For a scenic adventure, hike the Housatonic River Walk, 9.7km away, surrounded by stunning nature. Don’t miss the Catamount Aerial Adventure Park, 12.9km distant, featuring exhilarating ziplining and ropes courses.

Nightlife

Experience the vibrant nightlife in Sheffield by visiting the Mahaiwe Performing Arts Center for captivating performances, or enjoy a meal and live music at the Infinity Music Hall and Bistro. For a more theatrical atmosphere, check out the Berkshire Theatre Festival, offering a delightful mix of culture and entertainment.

*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, with Tuesday being the least expensive day for accommodation. Use Expedia's search tool to filter results by budget and hotel type, such as eco-friendly options, and explore package deals that combine flights and activities. This approach can help you find the best rates and member prices, ensuring a cost-effective stay while enjoying free local activities and attractions.

  • 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 set your budget, choose your ideal location, and more. You can arrange your search results to display prices from lowest to highest, allowing you to find the most affordable accommodation options first. Additionally, you can refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are available for booking.
  • Consider bundling your trip: You can save some dollars by combining your Sheffield hotel stay with your flights and activities through an Expedia package deal.

Find the best attractions near Sheffield

Sheffield is perfect for a skiing or adventure holiday, offering a range of outdoor activities. With its stunning national parks, nature reserves, and picturesque lakes, the area is ideal for those seeking eco-friendly experiences and a taste of the great outdoors. Explore the local attractions that cater to adventure enthusiasts and enjoy the beautiful natural surroundings of this charming Massachusetts town.

  • Bash Bish Falls State Park: Nestled 11.3km from Sheffield, this stunning national park features breathtaking waterfalls surrounded by lush greenery. It's perfect for hiking, photography, and immersing yourself in the great outdoors.
  • Housatonic River: Located 9.7km away, the Housatonic River offers serene views and fantastic opportunities for fishing, kayaking, and picnicking along its scenic banks. It’s an ideal spot to relax and enjoy nature.
  • Umpachene Falls Park: Just 6.4km from Sheffield, this enchanting waterfall park is a romantic getaway with picturesque views and walking trails. It's a fantastic place for adventure and enjoying a peaceful day outdoors.

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

When visiting Sheffield, Massachusetts, you have several major airports to choose from. Bradley International Airport (BDL) in Hartford, CT, is 59.5km away and offers hotels like the DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the terminal. Albany International Airport (ALB) in Albany, NY, is 80.5km away, with options such as the Park Manor Hotel, located 12.9km from the airport. Lastly, Stewart International Airport (SWF) in Newburgh, NY, is 91.7km distant, featuring hotels like The Dutchess Inn and Spa at Beacon, 9.7km away. Each hotel provides convenient access to its respective airport, ensuring a smooth travel experience.

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 The Yankee, Trademark Collection by Wyndham. 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?
Berkshire Mountain Lodge: Features free self parking, an indoor pool and complimentary wireless Internet access. The Yankee, Trademark Collection by Wyndham and Holiday Inn Club Vacations Oak n' Spruce Resort in the 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 32 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, Lime Kiln Farm Wildlife Sanctuary and Magnolia Bluffs Casino. A couple of additional sights to add to your itinerary are Drury Preserve and Ashley House. 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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