Sheffield Hotels from S$94

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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 S$210
includes taxes & fees
25 Nov - 26 Nov
Wilder House Berkshires

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1003)
"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 S$155
includes taxes & fees
14 Dec - 15 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 S$94
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, (801)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is S$135
includes taxes & fees
25 Nov - 26 Nov
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, (789)
"Place was great!"
United States
Benjamin
The price is S$174
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 S$239
includes taxes & fees
25 Nov - 26 Nov
The Cornell Inn, Lenox & The Berkshires

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is S$272
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 S$176
includes taxes & fees
25 Nov - 26 Nov
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 S$145
includes taxes & fees
14 Dec - 15 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 S$247
includes taxes & fees
25 Nov - 26 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, (697)
"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 S$156
includes taxes & fees
30 Nov - 1 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, (755)
"Clean room, very courteous staff "
United States
Thomas
The price is S$221
includes taxes & fees
30 Nov - 1 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 S$186
includes taxes & fees
30 Nov - 1 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 S$416
includes taxes & fees
25 Nov - 26 Nov
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 S$318
includes taxes & fees
25 Nov - 26 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 S$366
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 S$158
includes taxes & fees
25 Nov - 26 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.

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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 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 n’ Spruce Resort in the Berkshires by IHG: Embrace the spirit of adventure at the Holiday Inn Club Vacations Oak n’ 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 Expedia’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: Expedia’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
January23.2°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

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 Berkshire Mountain Lodge and Berkshires Untold. 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: Offers 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 33 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 Mount Everett State Reservation. A couple of additional sights to add to your itinerary are Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary. 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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