A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

Find hotels in Sheffield, MA from AED 230

  • 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

Property class

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Sheffield hotels

1. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."
United States
Liliana
The price is AED 602
AED 672 total
includes taxes & fees
1 Nov - 2 Nov
Wilder House Berkshires

2. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,001 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
United States
Lynne
The price is AED 278
AED 310 total
includes taxes & fees
22 Nov - 23 Nov
Quality Inn Great Barrington

3. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (819 reviews)
"Nice view and location for fall color."
United States
Md
The price is AED 528
AED 589 total
includes taxes & fees
3 Nov - 4 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

4. 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, (847 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
The price is AED 331
AED 369 total
includes taxes & fees
12 Nov - 13 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG

5. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (933 reviews)
"Super clean and cozy and safe"
United States
Andrea
The price is AED 220
AED 246 total
includes taxes & fees
1 Nov - 2 Nov
Monument Mountain Motel

6. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (58 reviews)
"East Rock was a nice, clean, and comfortable place to stay. Everything was great, and I enjoyed my stay."
United States
Sharon
The price is AED 475
AED 530 total
includes taxes & fees
29 Nov - 30 Nov
East Rock Inn

7. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (453 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
The price is AED 386
AED 444 total
includes taxes & fees
30 Oct - 31 Oct
Locust Tree Bed and Breakfast LLC

8. The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (95 reviews)
"Lovely property.unique historic buildings and rooms with updated amenities! Quiet and peaceful beautiful dinner!"
United States
mary ellen
The price is AED 1,065
AED 1,285 total
includes taxes & fees
1 Nov - 2 Nov
The Old Inn On The Green

9. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (251 reviews)
"Great Breakfast Bed was okay Room very quaint hotel was very nice inside"
United States
Melanie
The price is AED 656
AED 754 total
includes taxes & fees
1 Nov - 2 Nov
Blackberry River Inn

10. Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (150 reviews)
"Beyond amazing, we loved it so much!"
United States
Stacy
The price is AED 559
AED 626 total
includes taxes & fees
2 Nov - 3 Nov
Little Cat Lodge

11. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (626 reviews)
"Stay was great. Staff very friendly and helpful. 1 guest was screaming at someone at 4am but other than that it was a great stay"
United States
Sherry
The price is AED 290
AED 324 total
includes taxes & fees
30 Oct - 31 Oct
Travelodge by Wyndham Great Barrington Berkshires

12. The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (636 reviews)
"A fine place for a quick overnight trip to the Berkshires."
United States
David
The price is AED 308
AED 344 total
includes taxes & fees
2 Nov - 3 Nov
The Little Lion

13. The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (156 reviews)
"It’s an exceptional place in every aspect. "
United States
William
The price is AED 1,095
AED 1,260 total
includes taxes & fees
15 Nov - 16 Nov
The White Hart

14. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (110 reviews)
"We loved everything about Granville House, especially the innkeepers! Wonderful atmosphere and excellent food! It was definitely the highlight of our trip to New England."
United States
Cynthia
The price is AED 937
AED 1,046 total
includes taxes & fees
1 Nov - 2 Nov
Granville House

15. Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
10.0 out of 10, Exceptional, (48 reviews)
"Great stay!"
United States
Conor
The price is AED 1,020
AED 1,263 total
includes taxes & fees
29 Nov - 30 Nov
Prospect Berkshires

16. the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (289 reviews)
"Super cute, fairly clean and such a lovely breakfast!"
United States
Luis
The price is AED 606
AED 679 total
includes taxes & fees
20 Nov - 21 Nov
the Alander

17. The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (156 reviews)
"Great value. Excellent location. Responsive staff."
United States
Nelson
The price is AED 536
AED 600 total
includes taxes & fees
30 Oct - 31 Oct
The Brooks Motel

18. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
"Enjoyed staying in the old hotel and loved the large porch with the bar to relax on."
United States
Mallory
The price is AED 579
AED 829 total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn

19. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,000 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
The price is AED 403
AED 450 total
includes taxes & fees
22 Nov - 23 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel

20. Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (321 reviews)
"Over eight annual visits to this hotel, it has been a wonderful stay each time."
United States
mary
The price is AED 898
AED 1,033 total
includes taxes & fees
29 Nov - 30 Nov
Interlaken Inn & Resort
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.

A lakeside town with autumn foliage, a bridge, and a rocky shoreline.

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 Adventure: Sheffield offers thrilling activities like skiing, hiking, and exploring beautiful parks and lakes.
  • Charming Downtown: Discover historical sites and local shops in Sheffield's picturesque downtown area.
  • Relaxation Options: Unwind at local spas after a day of adventure or enjoy cozy accommodations.
  • Family-Friendly Atmosphere: The town provides a welcoming environment perfect for families and romantic getaways.
  • Unique Lodging: Choose from charming bed & breakfasts or agritourism properties for a memorable stay.

Find great hotels near Sheffield

Discover a range of charming accommodations in Sheffield, Massachusetts, perfect for your getaway. From cozy bed & breakfasts to unique agritourism properties, this picturesque town offers options for every traveler. Enjoy pet-friendly services and family-friendly experiences as you explore the area. Whether you're seeking the best hotels or looking for hotel reviews, Sheffield has a variety of lodging choices to ensure a memorable vacation.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled in the picturesque Berkshires, this 3.5-star resort is perfect for families and LGBTQIA travelers seeking a fun and welcoming vacation. Located 19.3km from Sheffield, the resort offers a variety of amenities tailored for children, including an Arcade Game Room, a shared Playground, and onsite Mini Golf. With ski shuttle access nearby, guests can easily hit the slopes or explore the stunning natural surroundings. This resort is designed for those looking to create unforgettable family memories while enjoying a range of recreational activities.
  • Quality Inn: Situated just 9.7km from Sheffield, Quality Inn is ideal for adventure seekers and business travelers alike. This comfortable lodging offers an array of outdoor activities, including snow tubing, snowboarding, and skiing rentals nearby, making it perfect for winter sports enthusiasts. For those who prefer to explore on foot or bike, hiking and biking trails are also available in the vicinity. With its convenient location and focus on adventure, Quality Inn is a great choice for those looking to blend work and play in a vibrant setting.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Located 11.3km from Sheffield, this hotel caters to LGBTQIA travelers and business visitors seeking a comfortable stay. The Holiday Inn Express offers modern amenities and a welcoming atmosphere, ensuring guests feel at home. Its affiliation with LGBTQI travel guides highlights its commitment to inclusivity. With easy access to local attractions and business centers, this hotel is a smart choice for those balancing work commitments with leisure activities in the beautiful Berkshires.

Where to stay near Sheffield

Sheffield, Massachusetts, offers a delightful blend of adventure and relaxation for your vacation. Explore the charming downtown filled with historical sites, or venture into the surrounding natural beauty perfect for outdoor activities. Nearby neighborhoods provide a romantic atmosphere and family-friendly vibes, making it an ideal getaway for all. With various vacation packages available, you'll find the best places to stay and experience the warm hospitality of friendly locals during your trip.

  • The Berkshires: Nestled 17.7km from Sheffield, The Berkshires is known for its stunning outdoor experiences and breathtaking scenery. A year-round destination, it sees peak visitor numbers during the summer months. This region is a paradise for adventure seekers, offering a range of activities such as skiing at its renowned ski resorts, hiking through lush mountains, and enjoying serene lakes. The Berkshires also hosts various events and conferences, making it a vibrant hub for culture and recreation.
  • Great Barrington: Located 9.7km from Sheffield, Great Barrington is a charming city that attracts visitors throughout the year. Known for its exhilarating ski fields and adventure sports, this destination peaks in the summer months. The city's proximity to scenic lakes and majestic mountains provides ample opportunities for outdoor enthusiasts. Parks in the area also offer relaxing spaces for picnics and leisurely strolls, making Great Barrington a perfect blend of excitement and tranquility.
  • Ashley Falls: Just 6.4km from Sheffield, Ashley Falls is a cozy city that offers a moderately seasonal travel experience, with peak visitors during the summer and fall. Known for its adventurous spirit, visitors flock to enjoy activities such as skiing and motor racing. The area is also home to beautiful lakes and a national state park, providing breathtaking landscapes and outdoor activities. Ashley Falls is an inviting destination for sports lovers and those seeking to connect with nature.

Things to do near Sheffield

Sheffield, Massachusetts, is a fantastic destination for adventure seekers and outdoor enthusiasts. Visitors can enjoy skiing at local resorts and explore beautiful parks. For relaxation, consider visiting a spa to unwind after a day of outdoor activities. Whether you're hitting the slopes or taking in the scenic views, Sheffield offers a variety of experiences for a memorable vacation.

Shopping

In Sheffield, you can shop at local favorites like Hoffman's Pottery, or visit the Berkshire Mountain Country Store, both located 24.1km away. If you're up for a drive, check out the Lee Premium Outlets, situated 22.5km away, featuring a variety of brand-name stores and family-friendly entertainment.

Recreation

Lake Mansfield Park offers a tranquil setting for relaxation, featuring scenic trails and serene waters perfect for unwinding. Music Mountain presents an entertaining concert experience, where you can enjoy live performances in a vibrant atmosphere. Greenock Country Club invites you to play golf in a beautiful outdoor setting, ideal for sports enthusiasts.

Adventure

Ski Butternut offers thrilling skiing experiences with excellent slopes and lively sports vibes, located 8.0km from Sheffield. For a scenic hike, the Housatonic River Walk, 9.7km away, immerses you in nature’s beauty. For a fun challenge, visit Catamount Aerial Adventure Park, 12.9km away, featuring exciting zipline courses.

Nightlife

Sheffield offers a charming nightlife with venues like the Mahaiwe Performing Arts Center, just 9.7km away, and the Infinity Music Hall and Bistro, 17.7km away, both featuring romantic and cultural performances. The Berkshire Theatre Festival, 19.3km from Sheffield, adds to the vibrant entertainment scene.

*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 during your visit to Sheffield, Massachusetts, consider traveling in January or March to April when accommodation prices are lower. Book your stay for a Tuesday, as it's the cheapest day, and compare room rates through Expedia for the best deals. Look for eco-friendly hotels and sort options by price to find budget-friendly stays. Additionally, consider package deals that combine flights, hotels, and activities for greater savings. Exploring free local attractions will also 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: Utilize Expedia’s search tool to customize your travel options according to your budget, desired location, and preferred hotel style. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Sheffield with your flights and activities through an Expedia package deal.

Find the best attractions in and around Sheffield

Sheffield, Massachusetts, is a fantastic destination for adventure seekers and outdoor enthusiasts. Visitors can explore national parks, nature reserves, and beautiful lakes, offering eco-friendly experiences and thrilling activities. For those planning their stay, there are several hotels conveniently located near Sheffield Botanical Gardens, ensuring a comfortable and enjoyable vacation surrounded by nature.

  • Taconic State Park: Discover the breathtaking beauty of Taconic State Park, located 12.9km from Sheffield. This park offers an array of outdoor adventures, including hiking, camping, and picnicking amid stunning natural scenery and diverse wildlife.
  • Housatonic River: Flowing 9.7km from Sheffield, the Housatonic River is a picturesque spot perfect for kayaking, fishing, or simply enjoying a leisurely stroll along its banks. The serene landscape invites outdoor enthusiasts to embrace nature's tranquility.
  • Ashley House: Situated in Sheffield, the Ashley House is a charming museum that offers a glimpse into local history and culture. Explore its exhibits and learn about the region's heritage in a beautifully preserved setting.

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

To reach Sheffield, Massachusetts, you have several airport options. Bradley International Airport (BDL) in Hartford, CT, is located 59.5km away. Nearby hotels include the DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport, and Simsbury 1820 House, 11.3km away. Albany International Airport (ALB) in Albany, NY, is 80.5km from Sheffield, with convenient hotel options like Park Manor Hotel and The Landing Hotel at Rivers Casino & Resort, both 12.9km from the airport. Stewart International Airport (SWF) in Newburgh, NY, is 511.3km away, featuring hotels such as The Dutchess Inn and Spa at Beacon, located 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 traveler data. This B&B offers free breakfast and free parking. Other good choices for your trip to the area are Berkshire Mountain Lodge and Quality Inn Great Barrington. See all available top hotels, or vacation rentals in Sheffield.
What are some of the best vacation home rentals that Sheffield has to offer?
Antique Farmhouse Totally Restored: This highly rated vacation home rental in Sheffield is located in a rural location and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. 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 room reservations are refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your check-in date. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.
Where can I learn more about changing or cancelling my trip to Sheffield?
To access more information about changing or cancelling your trip to Sheffield, go to https://www.expedia.com/service/.
What's the best place to stay near Ashley House?
Sheffield 1802 House is one of the top choices for your stay based on our traveler data, and this 3.5-star B&B offers free breakfast and free parking. It's located 3.2 mi (5.1 km) from Ashley House. Another good option is Locust Tree Bed and Breakfast, located 3.8 mi (6.2 km) away.
What about the best place to stay near Magnolia Bluffs Casino?
One of the top choices for your stay is Sheffield 1802 House, located 1.6 mi (2.6 km) from Magnolia Bluffs Casino, and this 3.5-star B&B offers free breakfast and free parking.
What are some accommodations with pools in Sheffield?
Berkshire Mountain Lodge: Provides 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 offer an onsite pool. View all hotels with pools in Sheffield.
What is the best accommodation for staying close to Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
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 accommodations to choose from. Find out more about Sheffield.
What should I see while I'm in Sheffield?
Favorite places to visit include Housatonic River, Suter Farm, and Ashley House. A couple of additional sights to add to your agenda are Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary. Check out what more to see and do in Expedia's Sheffield guide.
What's the weather like in Sheffield?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.