Sheffield hotels from RM289

Start date: Check-in selected.
To Date
End date: Check-out
  • 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

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Sheffield hotels

Wilder House Berkshires

2.0 star property
Sheffield
9.8 out of 10, Exceptional, (38)
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "
United States
Allison
The price is RM669
RM747 total
includes taxes & fees
30 Nov - 1 Dec
Wilder House Berkshires

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1004)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is RM439
RM490 total
includes taxes & fees
16 Dec - 17 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1007)
"Great stay!"
United States
Ann
The price is RM259
RM289 total
includes taxes & fees
7 Dec - 8 Dec
The Yankee, Trademark Collection by Wyndham

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (803)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is RM383
RM427 total
includes taxes & fees
30 Nov - 1 Dec
Berkshires Untold

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, (790)
"Place was great!"
United States
Benjamin
The price is RM440
RM549 total
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1001)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is RM532
RM756 total
includes taxes & fees
30 Nov - 1 Dec
The Cornell Inn, Lenox & The Berkshires

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1003)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is RM628
RM886 total
includes taxes & fees
21 Dec - 22 Dec
The Red Lion Inn

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (765)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge

The Brooks Motel

2.0 star property
Hillsdale
7.4 out of 10, Good, (116)
"Everything was lovely, thanks. Small note: the toilet seat needs a bolt on one side. Otherwise everything was great! Thx"
United States
Savannah
The Brooks Motel

the Alander

2.5 star property
Copake
9.0 out of 10, Wonderful, (182)
"Very nice clean place in a beautiful area. "
United States
Wayne
The price is RM661
RM740 total
includes taxes & fees
2 Dec - 3 Dec
the Alander

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (60)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is RM394
RM440 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (159)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is RM679
RM781 total
includes taxes & fees
27 Nov - 28 Nov
Blackberry River Inn

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
Great Barrington
8.8 out of 10, Excellent, (698)
"Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. "
United States
Tabitha
The price is RM442
RM494 total
includes taxes & fees
11 Dec - 12 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (756)
"Clean room, very courteous staff "
United States
Thomas
The price is RM624
RM697 total
includes taxes & fees
2 Dec - 3 Dec
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
9.2 out of 10, Wonderful, (587)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is RM504
RM563 total
includes taxes & fees
24 Dec - 25 Dec
Courtyard by Marriott Lenox Berkshires

Prospect Berkshires

3.0 star property
Egremont
9.6 out of 10, Exceptional, (14)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is RM1,074
RM1,338 total
includes taxes & fees
7 Dec - 8 Dec
Prospect Berkshires

Cornwall Inn and Lodge

3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (153)
"This inn was very quaint and welcoming. It was a nice inn for the value. "
United States
Jacqueline
The price is RM874
RM1,005 total
includes taxes & fees
27 Nov - 28 Nov
Cornwall Inn and Lodge

Inn at Pine Plains

3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (299)
"Great stay"
United Kingdom
Katherine
The price is RM1,022
RM1,156 total
includes taxes & fees
30 Nov - 1 Dec
Inn at Pine Plains

Locust Tree Bed and Breakfast LLC

3.0 star property
East Canaan
9.0 out of 10, Wonderful, (412)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is RM434
RM499 total
includes taxes & fees
29 Nov - 30 Nov
Locust Tree Bed and Breakfast LLC
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

Find out more about Sheffield

Top reasons to visit Sheffield

  • Outdoor Adventures: Sheffield is perfect for outdoor enthusiasts, offering skiing, apple picking, and exploration of nature reserves.
  • Stunning Scenery: Nestled in the Berkshires, visitors can experience breathtaking landscapes and serene lakes.
  • Rich History: The town's historical charm enhances its family-friendly and romantic atmosphere.
  • Art Galleries: Discover local art in charming galleries that reflect the town's creative spirit.
  • Diverse Accommodations: Enjoy a range of lodging options, from rustic agritourism to cosy bed and breakfasts.

Find great hotels near Sheffield

Discover a charming selection of accommodations in Sheffield, Massachusetts, perfect for your getaway. Whether you prefer the rustic charm of agritourism properties or the intimate atmosphere of bed and breakfasts, you'll find options that cater to families and pet-friendly travellers alike. Enjoy easy access to popular attractions in Sheffield and nearby Great Barrington, ensuring a delightful adventure awaits you in this picturesque region.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled 19.3km from Sheffield, this 3.5-star resort offers a welcoming atmosphere for LGBTQIA travellers and families alike. The resort's theme revolves around outdoor adventure and family fun, with easy access to ski activities and a plethora of children’s amenities. Guests can enjoy a playground, an arcade game room, and onsite mini-golf, ensuring a delightful experience for younger visitors. The property’s ski shuttle and lift access make it an ideal choice for winter sports enthusiasts, creating a perfect family vacation setting.
  • The Red Lion Inn: A captivating blend of history and adventure, The Red Lion Inn is also located 19.3km from Sheffield. This 3.5-star hotel is housed within a national historic building, offering guests a unique glimpse into the past. It caters to those seeking adventure, with various recreational activities available nearby, including skiing, sailing, and cycling. The inn’s rich historical theme is complemented by modern comforts, making it a superb choice for both business travellers and those looking to explore the Berkshires' scenic beauty.
  • Travelodge by Wyndham Great Barrington Berkshires: Situated 12.9km from Sheffield, the Travelodge offers a family-friendly and pet-friendly environment, making it an excellent choice for guests travelling with children or furry companions. This motel features essential amenities such as complimentary cribs for infants and a pet policy that permits dogs, ensuring a hassle-free stay. Its convenient location allows easy access to local attractions, allowing guests to unwind in comfort while enjoying the vibrant Berkshires region.

Where to stay near Sheffield

Sheffield, Massachusetts, offers a delightful blend of adventure and relaxation, perfect for any traveller. Nestled in the beautiful Berkshires, visitors can enjoy stunning scenery and charming evenings. The area's rich history complements its family-friendly atmosphere, making it ideal for romantic getaways or outdoor excursions. Don't miss exploring the picturesque surroundings and considering the best hotels in Sheffield for a comfortable stay. It's a perfect destination for those seeking both adventure and tranquillity.

  • The Berkshires: Nestled approximately 17.7km from Sheffield, The Berkshires is a stunning region celebrated for its breathtaking outdoor adventures and vibrant natural scenery. This area attracts visitors year-round, with peak arrivals during the warmer months of June to August. Outdoor enthusiasts flock here for skiing at the numerous ski resorts, as well as hiking and exploring picturesque lakes and mountains. Whether you’re looking to hit the slopes or enjoy a peaceful retreat amidst nature, The Berkshires promises an unforgettable experience.
  • Canaan: Located around 8.0km from Sheffield, Canaan is a charming city that offers a delightful mix of outdoor fun and scenic beauty. With visitor numbers soaring in April and the summer months, Canaan is perfect for those seeking adventure, from skiing to thrilling motor racing experiences. The area boasts stunning lakes, a vibrant stadium, and beautiful mountainous landscapes, making it an ideal spot for both relaxation and excitement. Canaan's welcoming atmosphere ensures a memorable visit for all who come.
  • Beartown State Forest: Situated roughly 16.1km from Sheffield, Beartown State Forest is a natural paradise that draws visitors with its lush forests and expansive parkland. This destination is popular for family-oriented activities and sports, particularly during the summer months of July and August. The forest offers various recreational opportunities, including hiking and exploring the nearby arena entertainment facility. With its proximity to natural parks and stadiums, Beartown State Forest is a fantastic choice for outdoor lovers seeking both adventure and tranquillity.

Things to do near Sheffield

Sheffield, Massachusetts, offers a delightful blend of adventure and outdoor activities, making it perfect for ski enthusiasts and nature lovers alike. Visitors can enjoy skiing at local resorts and fields, while also indulging in apple picking and exploring charming art galleries. Day trips and exciting rides provide fun for families, ensuring a memorable experience in this picturesque town.

Shopping

In Sheffield, you can enjoy shopping at local boutiques and quaint stores. If you're up for a drive, visit Lee Premium Outlets for a variety of brands or explore Hoffman's Pottery and Berkshire Mountain Country Store, both offering unique gifts and souvenirs about 24.1km away.

Recreation

Lake Mansfield Park offers a tranquil escape with its picturesque views and serene atmosphere, perfect for relaxation and rejuvenation. Enjoy the natural beauty of the area at Undermountain Golf Course, where you can engage in outdoor sports amidst lush landscapes, providing a refreshing experience for all golf enthusiasts.

For entertainment, Music Mountain presents delightful concerts in a charming setting, allowing you to unwind while enjoying live performances. This vibrant venue enhances the cultural experience, making it a wonderful addition to your wellness retreat in Sheffield.

Adventure

Experience the thrill of Ski Butternut, a ski field 8.0km from Sheffield, offering exhilarating slopes and a vibrant sports atmosphere. For a scenic hike, explore the Housatonic River Walk, located 9.7km away, where you can immerse yourself in nature's beauty. Don’t miss the Catamount Aerial Adventure Park, 12.9km from Sheffield, featuring exciting zip lines and ropes courses.

Nightlife

Experience the vibrant nightlife in Sheffield by visiting the Mahaiwe Performing Arts Center for a captivating show, or enjoy a meal at Infinity Music Hall and Bistro, where live performances create a delightful atmosphere. Don't miss out on the Berkshire Theatre Festival for more cultural entertainment.

*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 visit to Sheffield, consider travelling during the off-peak months of January and March to April, when accommodation prices dip. Tuesdays offer the lowest hotel rates, while Saturdays are the most expensive. Utilise Expedia’s search tool to find affordable options by sorting prices and filtering for eco-friendly hotels. To save further, consider booking a package that combines flights, hotels, and activities. Explore free local attractions and use public transport to keep travel costs down, ensuring a memorable yet economical holiday experience.

  • 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 desired location, and much more. You can organise your search results to display prices from lowest to highest, allowing you to easily find the most affordable hotels first. Additionally, you can refine your choices by hotel category; 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 money by combining your hotel reservation in Sheffield with your flights and activities by booking an Expedia package.

Find the best attractions near Sheffield

Sheffield, Massachusetts, is a haven for adventure and outdoor enthusiasts, offering a range of activities such as skiing and exploring nature reserves. Visitors can immerse themselves in the stunning landscapes of national parks and serene lakes, making it an ideal destination for those seeking eco-friendly experiences. Whether you're looking for thrilling adventures or tranquil retreats, Sheffield has something to offer every traveller.

  • Bash Bish Falls State Park: A stunning natural gem located 11.3km from Sheffield, Bash Bish Falls State Park offers breathtaking scenery and adventure. Visitors can hike through lush forests to witness the dramatic waterfalls, embracing the serenity of nature.
  • Housatonic River: Situated 9.7km away, the Housatonic River is perfect for leisurely strolls and picturesque views. This scenic river invites outdoor enthusiasts to enjoy activities like fishing, kayaking, and photography amid tranquil surroundings.
  • Three Mile Pond Wildlife Management Area: Located only 3.2km from Sheffield, this nature reserve is a haven for eco-friendly adventures. Explore diverse wildlife and engage in birdwatching while experiencing the beauty of untouched landscapes.

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 planning your trip to Sheffield, Massachusetts, there are several major airports to consider. Hartford, CT (BDL-Bradley Intl.) is 59.5km away, with nearby hotels such as the 4-star Simsbury 1820 House and the Marriott Hartford Downtown. Newburgh, NY (SWF-Stewart Intl.) is 91.7km from Sheffield, offering options like the Homewood Suites and The Dominion House Bed & Breakfast, both providing convenient transport services. Lastly, Albany, NY (ALB-Albany Intl.) is located 80.5km away, featuring hotels like The Landing Hotel at Rivers Casino & Resort and the Hilton Garden Inn Albany Medical Center, all easily accessible 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 The Red Lion Inn. See all available top hotels, or 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. The Red Lion Inn 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 34 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 Three Mile Pond Wildlife Management Area. A couple of additional sights to add to your itinerary are Mount Everett State Reservation and Thom Reed UFO Monument Park. 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.