Sheffield hotels from RM344

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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, (41)
"The place is lovely, room is cozy, and the bed is comfy"
United States
Mark
The price is RM659
RM737 total
includes taxes & fees
30 Dec - 31 Dec
Wilder House Berkshires

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is RM749
RM879 total
includes taxes & fees
29 Dec - 30 Dec
Lakehouse Inn

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (820)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is RM446
RM499 total
includes taxes & fees
24 Dec - 25 Dec
Berkshires Untold

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (190)
"The Alander has such a fun story, and was a great stay. We were just passing through for the night and it had everything we could need! It reminded me of Rosebud Motel group from Schitts Creek ;) if you know you know! Will definitely be staying again!"
United States
Jenna
The price is RM484
RM543 total
includes taxes & fees
24 Dec - 25 Dec
the Alander

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
United States
Lori
The price is RM611
RM864 total
includes taxes & fees
14 Jan - 15 Jan 2026
The Red Lion Inn

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (98)
"Great stay, comfortable place"
United States
barry
The price is RM525
RM588 total
includes taxes & fees
4 Jan - 5 Jan 2026
Inn at Silver Maple Farm

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is RM1,021
RM1,197 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Inn at Stockbridge

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1000)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
The price is RM680
RM783 total
includes taxes & fees
24 Dec - 25 Dec
The Cornell Inn, Lenox & The Berkshires

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (165)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is RM669
RM769 total
includes taxes & fees
6 Jan - 7 Jan 2026
Blackberry River Inn

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, (1007)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is RM408
RM456 total
includes taxes & fees
13 Jan - 14 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (89)
"Outstanding all around!"
United States
Jonathan
The price is RM912
RM1,019 total
includes taxes & fees
29 Dec - 30 Dec
Granville House

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (795)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is RM402
RM540 total
includes taxes & fees
11 Jan - 12 Jan 2026
Berkshire Mountain Lodge

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (273)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is RM729
RM838 total
includes taxes & fees
24 Dec - 25 Dec
Interlaken Inn & Resort

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is RM1,629
RM1,820 total
includes taxes & fees
18 Jan - 19 Jan 2026
33 Main

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (36)
"We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again."
United States
Laura
The price is RM545
RM609 total
includes taxes & fees
6 Jan - 7 Jan 2026
East Rock Inn

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (758)
"Clean room, very courteous staff "
United States
Thomas
The price is RM550
RM614 total
includes taxes & fees
8 Jan - 9 Jan 2026
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is RM1,242
RM1,498 total
includes taxes & fees
24 Dec - 25 Dec
The Old Inn On The Green

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (109)
"Great experience, looking forward to staying again."
United States
Greg
The price is RM611
RM684 total
includes taxes & fees
4 Jan - 5 Jan 2026
Changing Times Boutique Country Lodging

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is RM891
RM995 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hampton Terrace Inn

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (547)
"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "
United States
Maria
The price is RM448
RM500 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Little Lion
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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 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 The Yankee, Trademark Collection by Wyndham and Berkshire Mountain Lodge. 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?
The Yankee, Trademark Collection by Wyndham: Provides a seasonal outdoor pool, an indoor pool and buffet. Berkshire Mountain Lodge 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 34 hotels and other accommodation options to choose from. Find out more about Sheffield.
What are the top places to visit in Sheffield?
The picturesque setting of Housatonic River and Thom Reed UFO Monument Park exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Magnolia Bluffs Casino 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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