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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, (52 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is AU$327
includes taxes & fees
22 June - 23 June
Wilder House Berkshires

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,006 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is AU$176
includes taxes & fees
21 June - 22 June
The Yankee Inn

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,001 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is AU$149
includes taxes & fees
10 June - 11 June
Quality Inn Great Barrington

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (100 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
The price is AU$214
includes taxes & fees
14 June - 15 June
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (862 reviews)
"This is a great choice for folks traveling on a budget. Clean rooms, friendly owners, and nice retro vibe. Will be staying here again on my trips through the Berkshires."
United States
Mark
The price is AU$122
includes taxes & fees
14 June - 15 June
Monument Mountain Motel

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (418 reviews)
"Below average B&B"
United States
Larry
The price is AU$171
includes taxes & fees
9 June - 10 June
Locust Tree Bed and Breakfast LLC

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (863 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is AU$125
includes taxes & fees
8 June - 9 June
Howard Johnson by Wyndham Lenox

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (468 reviews)
"The breakfast was not diabetic friendly. They stated pet friendly but no place for dog to go to the bathroom. Had to walk dog through garbage . Cigarette butts all over very the place. Beds were terrible. My towels had clumps of black hair on them. Lotion and shampoos left in room were used not new ones. Will not go back"
United States
Stacy
The price is AU$104
includes taxes & fees
8 June - 9 June
Berkshire Travel Lodge

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (583 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is AU$125
includes taxes & fees
8 June - 9 June
Travelodge by Wyndham Great Barrington Berkshires

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (563 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is AU$139
includes taxes & fees
9 June - 10 June
The Little Lion

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
The price is AU$202
includes taxes & fees
8 June - 9 June
Berkshire Lake Lodge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (975 reviews)
"Very nice hotel. Highly recommend the restaurant."
United States
Thomas
The price is AU$198
includes taxes & fees
10 June - 11 June
Berkshires Untold

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)
"It was a clean, friendly hotel."
United States
Cheri
The price is AU$194
includes taxes & fees
10 June - 11 June
Quality Inn Lee - Lenox South

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (666 reviews)
"Decent place.friendly, quiet"
United States
William
The price is AU$113
includes taxes & fees
14 June - 15 June
Econo Lodge Lee - Great Barrington

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (966 reviews)
"Very quiet and clean will book again"
United States
Sade
The price is AU$224
includes taxes & fees
23 June - 24 June
Berkshire Mountain Lodge

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (460 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AU$237
includes taxes & fees
8 June - 9 June
Shaker Mill Inn

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (61 reviews)
"Comfortable stay "
United States
Paul
The price is AU$193
includes taxes & fees
8 June - 9 June
Becket Motel

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.6 out of 10, Excellent, (4 reviews)
"Wonderful pet-friendly property in a fantastic location. Everything in the village is just a short walk away, making it easy to enjoy local shops, restaurants, and attractions."
United States
Leonardo
The price is AU$168
includes taxes & fees
8 June - 9 June
Hideaway Inn Lenox

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,002 reviews)
"The property is in terrible condition."
United States
Olga V
The price is AU$97
includes taxes & fees
15 June - 16 June
Pleasant Valley Motel West Stockbridge

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (185 reviews)
"beautiful inn"
United States
Maura
The price is AU$245
includes taxes & fees
21 June - 22 June
Blackberry River 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 accommodation in 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.

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?
Luxury Private Estate in the Berkshires | Whitney by AvantStay: This highly rated holiday home rental in Sheffield offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of table football in this rental home to help you unwind. Our travellers also rate Antique Farmhouse Totally Restored as a favourite home for rent in Sheffield. 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 Inn 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 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 Thom Reed UFO Monument Park. A couple of additional sights to add to your itinerary are Lime Kiln Farm Wildlife Sanctuary and Three Mile Pond Wildlife Management Area. 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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