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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 NZ$276
includes taxes & fees
16 Apr - 17 Apr
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 NZ$117
includes taxes & fees
9 Apr - 10 Apr
Monument Mountain Motel

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (891 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 NZ$183
includes taxes & fees
14 Apr - 15 Apr
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 NZ$193
includes taxes & fees
9 Apr - 10 Apr
Shaker Mill Inn

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1,001 reviews)
"Great location, friendly staff"
United States
James
The price is NZ$129
includes taxes & fees
22 Apr - 23 Apr
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 NZ$276
includes taxes & fees
14 Apr - 15 Apr
Element Lenox Berkshires

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (896 reviews)
"Overall pleasant stay; great facilities, staff, and location"
United States
Casey
The price is NZ$206
includes taxes & fees
7 May - 8 May
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 NZ$135
includes taxes & fees
9 Apr - 10 Apr
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, (1,001 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is NZ$203
includes taxes & fees
21 Apr - 22 Apr
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 NZ$212
includes taxes & fees
9 Apr - 10 Apr
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, (576 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is NZ$145
includes taxes & fees
15 Apr - 16 Apr
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, (845 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
The price is NZ$152
includes taxes & fees
9 Apr - 10 Apr
Howard Johnson by Wyndham Lenox

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
The price is NZ$256
includes taxes & fees
14 Apr - 15 Apr
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 NZ$208
includes taxes & fees
14 Apr - 15 Apr
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 NZ$195
includes taxes & fees
28 Apr - 29 Apr
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 NZ$227
includes taxes & fees
16 Apr - 17 Apr
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 NZ$191
includes taxes & fees
9 Apr - 10 Apr
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 NZ$271
includes taxes & fees
14 Apr - 15 Apr
the Alander

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (98 reviews)
"Very cosy and friendly "
United States
Dominic
The price is NZ$335
includes taxes & fees
12 Apr - 13 Apr
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 NZ$386
includes taxes & fees
13 Apr - 14 Apr
The Berkshire Mountain Inn
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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 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 Yankee, Trademark Collection by Wyndham 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, 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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