A covered wooden structure with a sloped roof, surrounded by greenery and trees.

Sheffield Hotels from S$97

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22 Aug - 23 Aug
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23 Aug - 24 Aug
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4 Sept - 6 Sept

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Our top choices for Sheffield hotels

1. Wilder House Berkshires

Wilder House Berkshires
Sheffield
United States
Jennifer
S$279
includes taxes & fees
1 Sept - 2 Sept
Wilder House Berkshires

2. Quality Inn Great Barrington

Quality Inn Great Barrington
Great Barrington
United States
Sisile
S$131
includes taxes & fees
21 Sept - 22 Sept
Quality Inn Great Barrington

3. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
United States
BJORN
S$163
includes taxes & fees
20 Sept - 21 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG

4. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
East Canaan
United States
Regina
S$153
includes taxes & fees
29 Aug - 30 Aug
Locust Tree Bed and Breakfast LLC

5. East Rock Inn

East Rock Inn
Great Barrington
United States
ERIK
S$179
includes taxes & fees
14 Sept - 15 Sept
East Rock Inn

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
United States
Lisa
S$276
includes taxes & fees
27 Aug - 28 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

7. Monument Mountain Motel

Monument Mountain Motel
Great Barrington
United States
John
S$121
includes taxes & fees
1 Sept - 2 Sept
Monument Mountain Motel

8. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
Great Barrington
United States
Elspeth
S$112
includes taxes & fees
1 Sept - 2 Sept
Travelodge by Wyndham Great Barrington Berkshires

9. Little Cat Lodge

Little Cat Lodge
Copake Falls
United States
Kees
S$267
includes taxes & fees
23 Aug - 24 Aug
Little Cat Lodge

10. The Little Lion

The Little Lion
Great Barrington
United States
Anne
S$160
includes taxes & fees
8 Sept - 9 Sept
The Little Lion

11. Blackberry River Inn

Blackberry River Inn
Norfolk
United States
Cheryl
S$258
includes taxes & fees
23 Aug - 24 Aug
Blackberry River Inn

12. Gedney Farm

Gedney Farm
Great Barrington
United States
Jane
S$306
includes taxes & fees
23 Aug - 24 Aug
Gedney Farm

13. the Alander

the Alander
Copake
United States
Jerry
S$242
includes taxes & fees
31 Aug - 1 Sept
the Alander

14. Granville House

Granville House
Housatonic
United States
Nicole
S$390
includes taxes & fees
26 Aug - 27 Aug
Granville House

15. The Brooks Motel

The Brooks Motel
Hillsdale
United States
Nelson
S$193
includes taxes & fees
20 Sept - 21 Sept
The Brooks Motel

16. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
United States
Christine
S$155
includes taxes & fees
16 Sept - 17 Sept
Quality Inn Lee - Lenox South

17. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Patricia
S$289
includes taxes & fees
14 Sept - 15 Sept
The Red Lion Inn

18. Prospect Berkshires

Prospect Berkshires
Egremont
United States
Kellee
S$508
includes taxes & fees
17 Sept - 18 Sept
Prospect Berkshires

19. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
United States
Claudia
S$191
includes taxes & fees
8 Sept - 9 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort

20. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
Catherine
S$488
includes taxes & fees
1 Sept - 2 Sept
The Old Inn On The Green
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Stay near popular Sheffield attractions

Ashley House

Built in 1735, the Ashley House is where Elizabeth Freeman successfully sued for her freedom, helping end slavery in Massachusetts. Tour the historic rooms and learn about this pivotal chapter in American history.
See properties

Thom Reed UFO Monument Park

8.0/10 (1 review)
America's first officially documented UFO encounter is commemorated at this riverside park in Sheffield. Explore plaques about the Reed family's 1969 experience while enjoying Housatonic River views.
See properties

Bartholomews Cobble

Twin rocky knolls form this National Natural Landmark, home to one of North America's most diverse fern collections. Explore five miles of trails through forests and riverbanks for exceptional wildlife viewing.
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Bartholomew's Cobble

10.0/10 (1 review)
This National Natural Landmark features twin rocky knolls and North America's most diverse fern collection. Explore its trails through varied ecosystems while watching for peregrine falcons and rare plants.
See properties

Drury Preserve

Explore diverse ecosystems along a serene 2.4-mile trail through hemlock forests and calcareous wetlands. Cross wooden boardwalks to a tranquil pond where great blue herons and other wildlife await.
See properties

Lime Kiln Farm Wildlife Sanctuary

This wildlife sanctuary showcases diverse plant species across limestone ridges and conifer forests. Explore trails to spot numerous butterfly species and Pileated Woodpeckers in the tranquil Berkshires landscape.
See properties

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.

See all hotels in Sheffield
A covered wooden structure with a sloped roof, surrounded by greenery and trees.

Top Sheffield Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"We always stay here on our trips to and from Maine and New York, we love it. So appreciate the kind staff and the pool. Great and weโ€™ll see you next time!"
Rebecca 1-night trip
Posted 8 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 11 hours ago
Howard Johnson by Wyndham Lenox
Little Cat Lodge

Little Cat Lodge

10/10 Excellent
"The staff did ann excellent job communicating before we got there, while we were there, and even after we checked out. Good room, easily accessible, and beautiful area."
Kees 1-night trip
Posted 12 hours ago
Little Cat Lodge
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Everything was clean and well maintained. Very good included breakfast, close to Tanglewood, the Manor, the Norman Rockwell Museum, Lenox and Stockbridge."
Andrew 2-night trip
Posted 17 hours ago
The Yankee Inn
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

10/10 Excellent
"NA"
Shannon 1-night trip
Posted 18 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"Only real challengeโ€”getting on the hotel wifi was a frustrating challenge! And every time you left your room you had to get on again."
Judith 4-night trip
Posted 18 hours ago
Quality Inn Great Barrington
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

8/10 Good
"The staff were all very nice and polite."
ella 1-night trip
Posted 2 days ago
Hampton Inn & Suites Berkshires-Lenox
Wilder House Berkshires

Wilder House Berkshires

10/10 Excellent
"Breakfast was delicious and everyone was so nice there."
Shadan 2-night trip
Posted 4 days ago
Wilder House Berkshires
The Little Lion

The Little Lion

10/10 Excellent
"Clean, convenient, remotely operated by the owner, the Red Lion, a short distance away. We could use all the amenities offered by the Red Lion (meals, pool, hot tub) while staying at the much more reasonable Little Lion. A great bargain for Stockbridge!"
Joyce 1-night trip
Posted 6 days ago
The Little Lion

More cheap stays in Sheffield

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
S$112
10 Sept - 11 Sept
includes taxes & fees
7.6/10 Good! (901 reviews)
Howard Johnson by Wyndham Lenox
Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
S$131
21 Sept - 22 Sept
includes taxes & fees
8.6/10 Excellent! (1,019 reviews)
Quality Inn Great Barrington
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

170 Housatonic Street Lee MA
S$155
16 Sept - 17 Sept
includes taxes & fees
Quality Inn Lee - Lenox South
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

1055 South Street Pittsfield MA
S$180
9 Sept - 10 Sept
includes taxes & fees
9.4/10 Exceptional! (170 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Hideaway Inn Lenox

Hideaway Inn Lenox

11 Old Stockbridge Rd Lenox MA
S$189
22 Sept - 23 Sept
includes taxes & fees
7.8/10 Good! (40 reviews)
Hideaway Inn Lenox
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
S$224
14 Sept - 15 Sept
includes taxes & fees
9.2/10 Wonderful! (1,017 reviews)
The Yankee Inn

Find out more about Sheffield

Top reasons to visit Sheffield

  • Outdoor Adventures: Sheffield is a haven for outdoor enthusiasts, offering skiing, nature reserves, and scenic lakes for exploration.
  • Charming City Centre: Stroll through the welcoming Sheffield City Centre, where friendly locals enhance your visit.
  • Rich History: Discover Sheffield's intriguing history through its museums and cultural attractions.
  • Unique Accommodation: Enjoy a memorable stay in delightful bed and breakfasts and agritourism properties.
  • Scenic Relaxation: Unwind along the picturesque River Sheaf, perfect for a leisurely day.

Find great hotels near Sheffield

Discover the charming lodging options in Sheffield, Massachusetts, where agritourism properties and delightful bed and breakfasts offer a unique getaway. Whether you're seeking pet-friendly accommodations or a family-friendly adventure, Sheffield's hotels cater to all your travel needs. With a variety of options, you can enjoy a memorable stay in this picturesque town, perfect for a relaxing holiday experience.

  • Holiday Inn Club Vacations Oak nโ€™ Spruce Resort in the Berkshires by IHG: Embrace the spirit of adventure at the Holiday Inn Club Vacations Oak nโ€™ Spruce Resort, where the thrill of the outdoors meets business convenience. Set in the scenic Berkshires, this 3.5-star resort is perfect for those seeking a ski getaway or outdoor escapade. Amenities include a business centre for corporate travellers and easy access to skiing, snowboarding, and hiking activities nearby. Guests can enjoy the comfort of well-appointed accommodations while engaging in exciting on-site and local recreational activities, ensuring a memorable stay that caters to both leisure and business needs.
  • The Red Lion Inn: Step back in time at The Red Lion Inn, a historic 3.5-star gem located in a beautifully preserved national historic building. This charming hotel offers a unique blend of vintage elegance and modern comfort, making it ideal for history enthusiasts and business travellers alike. With multiple meeting rooms and a 24-hour business centre, it caters to professional needs while allowing pets to join in on the adventure. Guests appreciate the warm hospitality, rich heritage, and delightful amenities, perfect for a relaxing getaway or productive retreat.
  • The Little Lion: A quaint and welcoming 3-star motel, The Little Lion is perfect for pet lovers seeking a homely atmosphere. Located just 14.5km from Sheffield, this motel allows pets to stay free, making it an excellent choice for those who wish to travel with their furry companions. The relaxed and friendly environment combined with essential amenities ensures a comfortable stay for all guests. With its pet-friendly policy and convenient location, The Little Lion is a charming option for a casual getaway.

Where to stay near Sheffield

Sheffield, Massachusetts, offers a delightful blend of adventure and relaxation, making it an ideal destination for tourists. The city is perfect for skiing enthusiasts and sports lovers alike. Explore the charming Sheffield City Centre, where friendly locals create a welcoming atmosphere. Nearby, discover picturesque landscapes and family-friendly activities, ensuring a memorable vacation. With its rich history and romantic vibes, Sheffield promises an unforgettable experience for every traveller seeking a vibrant getaway.

  • Great Barrington: Located 9.7km from Sheffield, Great Barrington offers a vibrant mix of outdoor adventures and cultural experiences. The town is a popular destination for those seeking skiing and sports activities, particularly during the peak summer months. Visitors can enjoy the stunning natural beauty of nearby lakes, mountains, and the national state park. With its charming downtown area filled with shops, restaurants, and art galleries, Great Barrington provides a delightful travel experience for those looking to immerse themselves in both nature and local culture.
  • The Berkshires: Situated 17.7km away from Sheffield, The Berkshires is renowned for its breathtaking scenery and outdoor adventures. This region attracts visitors year-round, with peak travel occurring during the warm summer months. Known for its ski resorts and picturesque landscapes, The Berkshires is a paradise for nature lovers. You can explore the numerous lakes and mountains or attend events at local conference venues, ensuring a well-rounded experience filled with both relaxation and excitement.
  • Ashley Falls: Just 6.4km from Sheffield, Ashley Falls is a charming city that offers a moderate seasonal influx of visitors, particularly during the summer and autumn months. This area is perfect for those seeking skiing and sports activities, with ample opportunities for adventure enthusiasts. The local landmarks, including serene lakes and parks, provide a tranquil backdrop for relaxation. Ashley Falls combines small-town charm with outdoor excitement, making it an ideal spot for a memorable holiday.

Things to do near Sheffield

Sheffield, Massachusetts, offers a delightful blend of adventure and relaxation, making it perfect for sports enthusiasts and holidaymakers alike. Visitors can indulge in skiing at local resorts or explore intriguing museums and entertainment venues. For a more leisurely experience, unwind with a spa day or enjoy the scenic beauty along the River Sheaf. Whether seeking thrilling rides or tranquil escapes, Sheffield provides a memorable getaway for all.

Shopping

In Sheffield, you can explore local shops for unique gifts. If you're up for a drive, the nearby Lee Premium Outlets offers a variety of brands, while the Berkshire Mountain Country Store and Hoffman's Pottery, both 24.1km away, provide charming local finds and handcrafted items.

Recreation

Explore Lake Mansfield Park for a serene retreat, offering picturesque walking trails and a tranquil lake, perfect for relaxation. For sports enthusiasts, Undermountain Golf Course provides a challenging round of golf amidst beautiful landscapes, while Music Mountain hosts delightful concerts, ensuring an entertaining evening out.

Adventure

At Ski Butternut, located 8.0km from Sheffield, you can enjoy exhilarating skiing and snowboarding amidst stunning landscapes. The Housatonic River Walk, 9.7km away, offers a scenic hiking trail perfect for outdoor enthusiasts. For a thrilling experience, visit the Catamount Aerial Adventure Park, situated 12.9km from Sheffield, featuring ziplining and rope courses.

Nightlife

Experience Sheffield's vibrant nightlife by visiting the Mahaiwe Performing Arts Center, just 9.7km away, where culture and romance blend seamlessly. Alternatively, enjoy the lively atmosphere at Infinity Music Hall and Bistro or the Berkshire Theatre Festival, both offering delightful family-friendly entertainment within a short drive.

*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 on your trip to Sheffield, Massachusetts, consider visiting during the cheaper months of January and March to April, avoiding the peak summer season. Book your stay on a Tuesday for the best rates, and utilise Expediaโ€™s search tool to find budget-friendly accommodations by filtering options and sorting prices. Look for eco-certified hotels for sustainable choices, and maximise savings by bundling your hotel, flights, and activities in a package. Be on the lookout for hidden offers and great deals to ensure an economical holiday.

  • 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: Expediaโ€™s search tool enables you to specify your budget, preferred location, and various other criteria. You can organise your search results to display prices from lowest to highest, ensuring you find the most affordable hotels first. Additionally, you have the option to refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that are available for booking.
  • Consider bundling your trip: You can enjoy significant savings by combining your Sheffield hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Sheffield

Sheffield, Massachusetts, is an ideal destination for outdoor enthusiasts, offering opportunities for skiing, adventure, and sports. Visitors can explore local attractions such as national parks, nature reserves, and scenic lakes. For additional activities, consider visiting the Sheffield United, Sheffield Bus Museum, and nearby attractions like Sheffield Arena and Sheffield Town Hall. This charming locale promises an eco-friendly experience for those seeking adventure in nature.

  • Taconic State Park: Nestled 12.9km from Sheffield, Taconic State Park offers a blend of adventure and stunning scenery. Hike through its picturesque trails, explore lush forests, and revel in the great outdoors, making it perfect for nature enthusiasts.
  • Housatonic River: Located 9.7km away, the Housatonic River is a serene spot ideal for scenic views and outdoor activities. Enjoy kayaking, fishing, or simply relaxing along its banks while soaking in the tranquil environment.
  • Umpachene Falls Park: Just 6.4km from Sheffield, Umpachene Falls Park features a beautiful waterfall surrounded by nature. It's a romantic setting for picnics or adventure seekers looking to explore 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
January23.2ยฐF (-4.9ยฐC)Light RainMostly CloudyAverageSlightly Low
February24.8ยฐF (-4.0ยฐC)Light RainMostly CloudySlightly LowAverage
March32.5ยฐF (0.3ยฐC)Light RainMostly CloudyAverageSlightly Low
April44.2ยฐF (6.8ยฐC)Light RainMostly CloudyAverageSlightly Low
May55.9ยฐF (13.3ยฐC)Light RainMostly SunnyAverageAverage
June63.7ยฐF (17.6ยฐC)Light RainMostly SunnySlightly HighAverage
July69.8ยฐF (21.0ยฐC)Light RainMostly SunnySlightly HighSlightly High
August67.8ยฐF (19.9ยฐC)Light RainMostly SunnyAverageSlightly High
September60.8ยฐF (16.0ยฐC)Light RainMostly SunnySlightly HighAverage
October49.8ยฐF (9.9ยฐC)Light RainMostly SunnyAverageSlightly High
November37.8ยฐF (3.2ยฐC)Light RainMostly SunnySlightly LowAverage
December29.7ยฐF (-1.3ยฐC)Light RainMostly CloudySlightly LowAverage

The nearest major airports for your trip to Sheffield

Sheffield, Massachusetts, is conveniently accessible via several major airports. Hartford, CT (BDL-Bradley Intl.) is 59.5km away, with nearby hotels like the 4-star DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport. Newburgh, NY (SWF-Stewart Intl.) is located 91.7km from Sheffield, offering options like the 3.5-star Dutchess Inn and Spa at Beacon, situated 9.7km from the airport. Albany, NY (ALB-Albany Intl.) lies 80.5km away, with hotels such as the 3.5-star Crowne Plaza Albany - The Desmond Hotel, only 1.6km from the airport. Each airport provides various transportation services for easy access to and from these hotels.

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 Inn 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 Inn: Offers a seasonal outdoor pool, an indoor pool and buffet. Berkshire Mountain Lodge and Holiday Inn Express & Suites Pittsfield-Lenox-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 30 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, Three Mile Pond Wildlife Management Area and Suter Farm. 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 19ยฐC, while the coldest months are January and February, with an average of -2ยฐC. 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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