Sheffield hotels from HK$659

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Filter by

Guest rating
Guest rating
Star rating

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)
"It was a very pleasant hybrid of a classic BnB with the privacy of an air BnB. Host was on point and communicative. We loved hanging out downstairs in the living room(s). Breakfast was fabulous "
United States
Evan M
Wilder House Berkshires

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 place to stay for a night in Great Barrington. Walk to everything in town "
United States
robert
The price is HK$590
HK$659 total
includes taxes & fees
9 Feb - 10 Feb
Quality Inn Great Barrington

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, (727 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is HK$834
HK$932 total
includes taxes & fees
1 Feb - 2 Feb
Holiday Inn Express Hotel & Suites Great Barrington by IHG

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,011 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is HK$722
HK$807 total
includes taxes & fees
1 Feb - 2 Feb
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, (1,001 reviews)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is HK$789
HK$881 total
includes taxes & fees
8 Feb - 9 Feb
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (818 reviews)
"Unbelieveably clean for the price."
United States
Micah
Monument Mountain Motel

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (16 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is HK$1,084
HK$1,211 total
includes taxes & fees
8 Feb - 9 Feb
Element Lenox Berkshires

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (567 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is HK$585
HK$653 total
includes taxes & fees
25 Jan - 26 Jan
Travelodge by Wyndham Great Barrington Berkshires

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (444 reviews)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is HK$790
HK$867 total
includes taxes & fees
25 Jan - 26 Jan
Shaker Mill Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is HK$1,123
HK$1,317 total
includes taxes & fees
7 Feb - 8 Feb
Lakehouse Inn

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (844 reviews)
"So charming, clean, thoughtful touches and a really special place!"
United States
Juliana
The price is HK$688
HK$769 total
includes taxes & fees
25 Jan - 26 Jan
Berkshires Untold

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,001 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is HK$656
HK$733 total
includes taxes & fees
6 Feb - 7 Feb
Quality Inn Lee - Lenox South

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (818 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is HK$769
HK$1,034 total
includes taxes & fees
1 Feb - 2 Feb
Berkshire Mountain Lodge

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,006 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is HK$1,128
HK$1,609 total
includes taxes & fees
22 Feb - 23 Feb
The Red Lion Inn

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"The room and amenities were amazing. "
United States
Kathleen
The price is HK$867
HK$968 total
includes taxes & fees
1 Feb - 2 Feb
Hampton Inn & Suites Berkshires-Lenox

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (825 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is HK$940
HK$1,203 total
includes taxes & fees
26 Jan - 27 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (37 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is HK$927
HK$1,035 total
includes taxes & fees
12 Feb - 13 Feb
East Rock Inn

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (830 reviews)
"Staff was very friendly and helpful."
United States
Pamela
The price is HK$616
HK$688 total
includes taxes & fees
25 Jan - 26 Jan
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, (414 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is HK$819
HK$941 total
includes taxes & fees
30 Jan - 31 Jan
Locust Tree Bed and Breakfast LLC

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, (75 reviews)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
The price is HK$993
HK$1,109 total
includes taxes & fees
29 Jan - 30 Jan
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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.
Save an average of 15% on thousands of hotels when you're signed in

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

Hotels in Sheffield with star-rating

Find out more about Sheffield

Top reasons to visit Sheffield

  • Outdoor Adventures: Sheffield offers thrilling activities like skiing and hiking amidst stunning national parks and serene nature reserves.
  • Charming Local Culture: Discover local art galleries and engage with the rich history of the area, providing a taste of its unique heritage.
  • Family-Friendly Fun: Enjoy apple picking and exciting rides, ensuring a delightful experience for visitors of all ages.
  • Picturesque Accommodations: Stay in charming agritourism properties and inviting bed and breakfasts in a friendly community setting.
  • Scenic Day Trips: Explore nearby attractions for memorable excursions in the picturesque Berkshires.

Find great hotels near Sheffield

Sheffield, Massachusetts, offers a delightful array of accommodation options, including charming agritourism properties and inviting bed and breakfasts. Perfect for families and pet-friendly travellers alike, you can enjoy a memorable vacation experience surrounded by nature. With convenient access to nearby attractions and accommodations in Great Barrington, Sheffield is an ideal destination for those seeking adventure and relaxation in the picturesque Berkshires.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled in the picturesque Berkshires, this 3.5-star resort combines comfort with family-friendly amenities, making it ideal for a fun-filled vacation. Located 19.3km from Sheffield, it offers easy access to skiing activities and other winter sports. The resort boasts an array of facilities tailored for children, including an arcade game room, a shared playground, and onsite mini-golf. With options for relaxing stays or exciting adventures, this resort is perfect for families and business travellers alike, ensuring a memorable experience for all.
  • Quality Inn: Situated a mere 9.7km from Sheffield, Quality Inn caters to the adventurous spirit in every traveller. This accommodation is perfect for those seeking business travel or thrilling outdoor experiences. Guests can indulge in a variety of adventure sports, such as skiing lessons, snowboarding, snow tubing, and hiking or biking nearby. The hotel's focus on recreation ensures that each guest can enjoy both relaxation and excitement during their stay, making it an excellent choice for active visitors.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Located 11.3km from Sheffield, the Holiday Inn Express Hotel & Suites Great Barrington is an inviting choice for business travellers and those seeking an LGBTQIA welcoming environment. This hotel prides itself on inclusivity and comfort, providing essential amenities for a pleasant stay. Its affiliation with LGBTQI travel guides ensures that all guests feel at home, making it a friendly and accommodating option for anyone visiting the area.

Where to stay near Sheffield

Sheffield, Massachusetts, offers a delightful escape for travellers seeking adventure and relaxation amidst the stunning Berkshire surroundings. Explore the charming local history, enjoy beautiful evenings, and soak in the serene scenery. Nearby, you'll find family-friendly activities and romantic spots perfect for couples. The area boasts a range of accommodations, ensuring a pleasant stay in this friendly community. Discover the best of Sheffield and its picturesque surroundings for an unforgettable holiday experience.

  • The Berkshires: Located 17.7km from Sheffield, The Berkshires is a picturesque region known for its stunning landscapes and outdoor adventures. Visitors flock here for a blend of activities such as skiing, hiking, and enjoying the breathtaking scenery throughout the year. The area boasts several ski resorts and fields, making it a winter wonderland during the colder months. With tranquil lakes and majestic mountains, The Berkshires offers an ideal backdrop for both relaxation and exploration, particularly in the summer months when outdoor activities are at their peak.
  • Great Barrington: Just 9.7km from Sheffield, Great Barrington is a vibrant city that attracts outdoor enthusiasts and sports lovers alike. The city experiences a steady influx of visitors year-round, with peaks during the summer months. Known for its excellent skiing opportunities and charming downtown area, Great Barrington features inviting parks and lovely lakes perfect for leisurely strolls. This city captures the essence of adventure, inviting travellers to indulge in a variety of sports and outdoor activities, all while enjoying the natural beauty that surrounds it.
  • Mount Washington: A quaint village situated 8.0km from Sheffield, Mount Washington offers a serene escape for those seeking outdoor experiences. The village showcases remarkable scenery, particularly for hikers and skiers drawn to its natural beauty and adventure opportunities. With its proximity to national state parks and stunning mountain peaks, Mount Washington is perfect for nature lovers. The area sees a consistent flow of visitors, particularly in February and during the summer, making it an excellent destination for those looking to immerse themselves in the great outdoors.

Things to do near Sheffield

Sheffield, Massachusetts, offers a delightful blend of adventure and relaxation, perfect for outdoor enthusiasts. Engage in thrilling activities such as skiing at local resorts, or enjoy a leisurely day of apple picking. Art galleries provide a taste of local culture, while family outings and exciting rides ensure fun for all ages. Don't miss the opportunity to explore nearby attractions on day trips, making Sheffield a charming destination for your vacation.

Shopping

In Sheffield, you can enjoy local shopping experiences at charming stores like Hoffman's Pottery. If you're up for a drive, visit Lee Premium Outlets, located 22.5km away, offering a range of brand-name outlets, or the Berkshire Mountain Country Store, situated 24.1km from Sheffield.

Recreation

Lake Mansfield Park offers a tranquil retreat with picturesque views and serene walking paths, perfect for relaxation and rejuvenation. Music Mountain hosts delightful concerts, providing an entertaining atmosphere to unwind. For outdoor enthusiasts, Undermountain Golf Course delivers a refreshing sporting experience amidst beautiful landscapes.

Adventure

At Ski Butternut, 8.0km from Sheffield, experience exhilarating skiing amidst a vibrant sports atmosphere. Alternatively, the Catamount Ski Area, 12.9km away, offers thrilling slopes for snow enthusiasts. For a scenic adventure, the Housatonic River Walk, 9.7km distant, features picturesque hiking trails surrounded by nature.

Nightlife

Experience the vibrant nightlife in Sheffield by visiting the Mahaiwe Performing Arts Center for live performances, or enjoy a meal and music at Infinity Music Hall and Bistro. For a classic theatre experience, catch a show at the Berkshire Theatre Festival, all offering enchanting cultural vibes.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Sheffield

For a budget-friendly trip to Sheffield, consider visiting in January or March to April, when accommodation prices are lower. Tuesday is the most economical day to stay, while Saturday tends to be pricier. Use Expedia to find the best hotel deals by sorting prices from lowest to highest. Combining your hotel, flights, and activities into one package can also yield savings. Explore free activities in the area to further enhance your experience without straining your budget.

  • 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 choices based on your budget, preferred location, and the type of hotel you desire. To find the most affordable prices and offers, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel booking in Sheffield with your flights and activities through an Expedia package.

Find the best attractions near Sheffield

Sheffield, Massachusetts, offers an ideal destination for adventure and outdoor enthusiasts. With its stunning national parks, serene nature reserves, and picturesque lakes, visitors can indulge in eco-friendly activities and thrilling adventures. Whether you're skiing in the winter or enjoying hiking and exploring the natural beauty during warmer months, Sheffield promises a memorable escape into the great outdoors.

  • Haystack Mountain State Park: Experience breathtaking views and invigorating hikes in this stunning national park. With trails that wind through lush forests and rocky terrains, it’s perfect for outdoor enthusiasts seeking adventure and scenic beauty.
  • Housatonic River: Enjoy leisurely strolls along the banks of the Housatonic River, where the tranquil waters offer a serene backdrop for picnics and nature photography. This picturesque river is ideal for fishing and canoeing, connecting you with the local wilderness.
  • Three Mile Pond Wildlife Management Area: Immerse yourself in the eco-friendly vibes of this nature reserve, perfect for birdwatching and hiking. Discover diverse wildlife while exploring well-maintained trails that showcase the area's natural beauty.

Best time to go to Sheffield

The best time to visit Sheffield is dependent 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

For your visit to Sheffield, Massachusetts, you can fly into several major airports. ALBany International Airport (ALB) is situated 80.5km away, with notable hotels like the Park Manor Hotel and The Landing Hotel at Rivers Casino & Resort, both 12.9km from the airport. Hartford's Bradley International Airport (BDL) is 59.5km from Sheffield, offering options like the DoubleTree by Hilton Hartford and Simsbury 1820 House, 1.6km and 11.3km away, respectively. Lastly, Stewart International Airport (SWF) in Newburgh, 511.3km from Sheffield, features hotels such as The Dutchess Inn and Spa at Beacon, just 9.7km 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?
Antique Farmhouse Totally Restored: This highly rated holiday home rental in Sheffield is located in a rural location, 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. 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. 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 Drury Preserve. A couple of additional sights to add to your itinerary are Ashley House and Mount Everett State Reservation. 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.

Explore a world of travel with Expedia