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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 reviews)
"The place is lovely, room is cozy, and the bed is comfy"
United States
Mark
$179 nightly
The price is $200
Jan 19 - Jan 20
Total with taxes and fees
Wilder House Berkshires

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (73 reviews)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
$123 nightly
The price is $137
Jan 25 - Jan 26
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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, (761 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
$135 nightly
The price is $151
Jan 26 - Jan 27
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18 reviews)
"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
$216 nightly
The price is $241
Jan 13 - Jan 14
Total with taxes and fees
Prospect Berkshires

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
$105 nightly
The price is $121
Jan 12 - Jan 13
Total with taxes and fees
Locust Tree Bed and Breakfast LLC

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (134 reviews)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
$206 nightly
The price is $226
Jan 12 - Jan 13
Total with taxes and fees
Gedney Farm

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (810 reviews)
"great stall and friendly pet friendly place"
United States
bonnie
$108 nightly
The price is $120
Feb 10 - Feb 11
Total with taxes and fees
Berkshire Mountain Lodge

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 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
$336 nightly
The price is $368
Jan 12 - Jan 13
Total with taxes and fees
The Old Inn On The Green

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,001 reviews)
"My go to place for my ski weekends"
United States
Ryan
$76 nightly
The price is $85
Jan 25 - Jan 26
Total with taxes and fees
Quality Inn Great Barrington

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (166 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
$164 nightly
The price is $189
Jan 12 - Jan 13
Total with taxes and fees
Blackberry River Inn

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.0 out of 10, Very Good, (9 reviews)
"Beautiful property, only stayed one night for business but it was very nice. Great burger at the restaurant downstairs! Possibly one of the best burgers I’ve ever had!"
United States
Jason
$179 nightly
The price is $203
Jan 12 - Jan 13
Total with taxes and fees
The Millerton Inn

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, (717 reviews)
"Nice warm pool and hot tub. Good little fitness center. "
United States
Fawn
$98 nightly
The price is $109
Jan 25 - Jan 26
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (814 reviews)
"Room was very well designed and clean. The woman who worked at the desk was wonderful!"
United States
Cynthia
$67 nightly
The price is $74
Jan 12 - Jan 13
Total with taxes and fees
Monument Mountain Motel

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (275 reviews)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
$191 nightly
The price is $220
Feb 8 - Feb 9
Total with taxes and fees
Interlaken Inn & Resort

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (440 reviews)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
$108 nightly
The price is $119
Jan 15 - Jan 16
Total with taxes and fees
Shaker Mill Inn

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (661 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
$128 nightly
The price is $143
Jan 23 - Jan 24
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Very comfortable beds! "
United States
Gerald
$111 nightly
The price is $124
Jan 25 - Jan 26
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (832 reviews)
"Great hospitality and beautiful design. Our family had a great time!"
United States
Alison
$121 nightly
The price is $135
Jan 14 - Jan 15
Total with taxes and fees
Berkshires Untold

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
$174 nightly
The price is $198
Jan 16 - Jan 17
Total with taxes and fees
Brook Farm Inn

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (37 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
$129 nightly
The price is $145
Jan 19 - Jan 20
Total with taxes and fees
East Rock Inn
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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

Hotels in Sheffield with star-rating

Find out more about Sheffield

Top reasons to visit Sheffield

  • Adventure Sports: Sheffield is a haven for outdoor enthusiasts, offering excellent skiing and various sports activities.
  • Scenic Nature: Visitors can explore stunning parks, lakes, and nature reserves, perfect for eco-friendly adventures.
  • Charming Accommodations: Enjoy a range of lodging options, from cozy bed & breakfasts to unique agritourism stays.
  • Rich Historical Atmosphere: Sheffield's charming vibe and friendly locals create a memorable vacation experience.
  • Relaxation Opportunities: Unwind at local spas and enjoy leisure activities amidst beautiful natural surroundings.

Find great hotels near Sheffield

Discover a charming selection of accommodations in Sheffield, Massachusetts, perfect for every type of traveler. From cozy bed & breakfasts to unique agritourism properties, Sheffield offers pet-friendly options and family-friendly facilities for an unforgettable adventure vacation experience. Explore the best hotels, read reviews, and find the perfect lodging to suit your needs while enjoying the beautiful surroundings of the Berkshires.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Nestled in the heart of the Berkshires, this 3.5-star resort offers a perfect blend of adventure and family-friendly amenities. With a focus on outdoor activities, guests can enjoy easy access to ski lifts, snowboarding, and hiking trails nearby. The resort is designed for families, featuring a mini-golf course, arcade game room, and a playground for children. Whether you’re hitting the slopes or relaxing with loved ones, this resort promises a fun-filled experience for guests of all ages.
  • Quality Inn: Located just 6 miles from Sheffield, Quality Inn is ideal for those combining business and adventure. This property caters to business travelers with essential amenities such as meeting rooms and a business center. For the adventure-seekers, nearby activities include snowshoeing, downhill skiing, and snowboarding, making it an excellent choice for those wanting to mix work with play. The welcoming atmosphere and convenient location make it an attractive option for both professionals and leisure travelers.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Just 7 miles from Sheffield, this hotel stands out as a welcoming space for business and LGBTQIA travelers. With 24-hour business center access and conference facilities, it’s perfect for meetings and corporate events. Guests appreciate the inclusive environment, making it a comfortable retreat. The hotel’s modern amenities, combined with a commitment to hospitality, ensure a pleasant stay for anyone visiting the area, whether for work or leisure.

Where to stay near Sheffield

Sheffield, Massachusetts, offers an ideal getaway for tourists seeking adventure and relaxation. With its charming historical vibe, you'll find an array of family-friendly activities and stunning scenery. Nearby cities and neighborhoods provide a romantic atmosphere and friendly locals, making it perfect for a memorable vacation. Explore Sheffield's ski resorts and outdoor sports, and don't miss out on exciting vacation packages that highlight the best places to visit within walking distance. Your adventure awaits.

  • Great Barrington: Located 6 miles from Sheffield, Great Barrington is a charming city that attracts visitors year-round, particularly during the summer months from June to August. Known for its outdoor adventure offerings, this inviting destination is popular for skiing and sports enthusiasts. Visitors can enjoy the nearby ski fields and resorts, making it a perfect spot for thrill-seekers. The area's natural beauty includes serene lakes and majestic mountains, complemented by the stunning landscapes of the national state park. Great Barrington is an ideal base for adventure lovers looking to immerse themselves in the great outdoors.
  • The Berkshires: Situated 11 miles from Sheffield, The Berkshires is famed for its breathtaking scenery and outdoor activities. This region experiences steady visitor traffic throughout the year, with peaks in the summer months from June to August. Renowned for its skiing opportunities, The Berkshires offers a wealth of adventure for nature lovers. In addition to ski resorts, visitors can explore beautiful lakes and mountains, providing a perfect backdrop for hiking, fishing, or simply enjoying the picturesque views. The event conference venues also make it a great location for cultural experiences and gatherings.
  • Ashley Falls: Just 4 miles from Sheffield, Ashley Falls is a quaint city that sees moderate seasonal traffic, peaking during the summer and fall months. Visitors are drawn here for its exciting ski and sports offerings, along with a variety of adventure experiences. The nearby ski fields and resorts cater to winter sports enthusiasts, while the local parks and town hall enhance the community's charm. Ashley Falls blends adventure with small-town hospitality, making it a delightful stop for travelers looking to enjoy both outdoor activities and a warm, welcoming atmosphere.

Things to do near Sheffield

Sheffield, Massachusetts, is perfect for adventure seekers and sports enthusiasts, offering fantastic skiing opportunities at local ski resorts and fields. Visitors can explore numerous parks for outdoor activities and unwind at a spa show for relaxation. With its blend of recreation and leisure, Sheffield promises an exciting vacation experience for everyone.

Shopping

In Sheffield, you'll find local charm at shops like Hoffman's Pottery. If you're up for a drive, Lee Premium Outlets and Berkshire Mountain Country Store, both 14 and 15 miles away respectively, offer a wider selection of gifts and souvenirs in a vibrant shopping atmosphere.

Recreation

Experience tranquility at Lake Mansfield Park, where you can unwind in nature and enjoy serene walks around the lake. For music lovers, Music Mountain offers delightful concerts in a picturesque setting. If you're in the mood for sports, the Greenock Country Club provides a beautiful golf course for outdoor recreation.

Adventure

At Ski Butternut, located 5 miles from Sheffield, enjoy thrilling skiing experiences with vibrant sports energy. The Housatonic River Walk, 6 miles away, offers scenic hiking adventures amidst beautiful outdoor landscapes. For a unique challenge, try the Catamount Aerial Adventure Park, situated 8 miles from Sheffield, featuring exciting zipline courses.

Nightlife

Experience the vibrant nightlife in Sheffield by catching a show at the nearby Mahaiwe Performing Arts Center or enjoy a delightful evening at Infinity Music Hall and Bistro. For a touch of tradition, don’t miss the Berkshire Theatre Festival, all offering a blend of culture and family-friendly entertainment.

*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, visit during the off-peak months of January and March to April for lower lodging prices. Tuesdays are the most affordable days to stay, while Saturdays are the priciest. Use Expedia to compare hotel rates and book package deals that combine flights and activities for additional savings. Consider eco-certified hotels for budget-friendly options. Joining Expedia's One Key membership can provide exclusive discounts and allow you to earn rewards for future bookings. Walking is also a great way to explore Sheffield without spending on transportation.

  • 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 narrow down your options based on your preferences, such as budget, desired location, and hotel type. For instance, selecting the Eco-certified filter will show you 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 Sheffield hotel reservation with your flights and activities through an Expedia package deal.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Sheffield

Sheffield, Massachusetts, is perfect for outdoor enthusiasts seeking ski adventures, sports vacations, and eco-friendly experiences. Explore local attractions like national parks, nature reserves, and beautiful lakes, ideal for adventure seekers. If you're looking for accommodations, consider hotels near Sheffield Botanical Gardens for a relaxing stay amidst nature.

  • Taconic State Park: Located 8 miles from Sheffield, this national park offers breathtaking scenery and a wealth of outdoor adventure opportunities. Hike through lush trails, enjoy stunning vistas, and experience the tranquility of nature in a pristine setting.
  • Housatonic River: Just 6 miles away, the Housatonic River provides beautiful views and a serene atmosphere perfect for kayaking, fishing, or simply relaxing by the water. Its lush banks are ideal for picnicking and enjoying the great outdoors.
  • Umpachene Falls Park: Only 4 miles from Sheffield, this enchanting waterfall park is perfect for outdoor enthusiasts. Its romantic vibes make it a great spot for couples, while the adventurous trails invite exploration amid stunning 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

When planning your trip to Sheffield, Massachusetts, there are several major airports to consider. Hartford, CT (BDL-Bradley Intl.) is located 37 miles away, with nearby hotels like the DoubleTree by Hilton Hartford - Bradley Airport, just 1 mile from the airport. Albany, NY (ALB-Albany Intl.) is 50 miles away, offering options such as the Park Manor Hotel, 8 miles from the airport. Lastly, Newburgh, NY (SWF-Stewart Intl.) is 57 miles from Sheffield, with accommodations like The Dutchess Inn and Spa at Beacon, 6 miles from the airport. Each airport provides convenient access to these hotels and the surrounding areas.

Frequently asked questions

What is the best area to stay in Sheffield?
The best area to stay in Sheffield is the town center, particularly around Main Street (Route 7), for its accessibility and access to local establishments.

This area provides a convenient base with a selection of inns and guesthouses. Main Street is where you'll find local shops, restaurants, and art galleries, making it easy to explore the town on foot. It's also well-situated for exploring the surrounding Berkshire Hills.

Couples looking for a peaceful retreat will appreciate the options just outside the immediate town center. These accommodations often offer a more secluded setting with views of the natural landscape, while still being a short drive from Sheffield's amenities and nearby attractions like the Berkshire Botanical Garden.

For solo travelers, staying near Main Street offers the convenience of easily accessing local dining and shops.
What are the best hotels in Sheffield that travelers recommend?
For an excellent hotel in Sheffield that travelers highly recommend, consider the Wilder House Berkshires.

The Wilder House Berkshires, with an outstanding 9.8 rating, offers guests comfortable and clean rooms with premium bedding and air conditioning. Guests consistently praise the great and delicious free cooked breakfast, and complimentary self-parking is also available, adding to the convenience of your stay.
What are the best family hotels in Sheffield?
For families traveling to Sheffield, Wilder House Berkshires is an excellent option.

This highly-rated property, with a 9.8 review score, offers a comfortable and clean stay for families. Guests frequently praise the great and delicious breakfast, and the hotel provides several complimentary amenities that are beneficial for family travel, including a free crib, free breakfast, free cooked breakfast, free self-parking, free toiletries, and free WiFi.
What hotels in Sheffield offer free breakfast?
For hotels in Sheffield offering complimentary breakfast, consider the Wilder House Berkshires.

The Wilder House Berkshires, with an outstanding 9.8 rating, provides a highly-rated experience. Guests frequently praise the comfortable and clean rooms, as well as the great and delicious breakfast, which includes a cooked option. This hotel also offers free self-parking, free toiletries, and free WiFi, ensuring a convenient stay. It is located approximately 6.4 miles from the Housatonic River.
What are the best budget hotels in Sheffield?
For a highly-rated budget hotel in Sheffield, the Wilder House Berkshires is an excellent choice.

This hotel, with an outstanding 9.8 review rating, offers a comfortable and clean stay with several complimentary amenities. Guests particularly appreciate the free self-parking, free toiletries, and a delicious free cooked breakfast. Additionally, the hotel provides free WiFi and air conditioning for a pleasant stay. It's located within 6.4 miles of the Housatonic River. View all budget hotels in Sheffield
When is the best time to go to Sheffield?
The best time to visit Sheffield, Massachusetts, is during the autumn months, from September to November, for its renowned fall foliage, or in the summer, from June to August, for outdoor activities and pleasant weather.

Autumn transforms the Berkshire landscape with vibrant colors, making it ideal for scenic drives and exploring the charming small towns. The weather is generally crisp and comfortable, superb for hiking or visiting local farms and orchards. This season is particularly appealing to couples looking for a picturesque and romantic getaway.

Summer offers warm temperatures and a full calendar of outdoor events and festivals. It's an excellent time for activities like kayaking on the Housatonic River, cycling on country roads, or exploring the numerous art galleries and studios in the area.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Sheffield.
How can I save on a Sheffield hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Sheffield hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Sheffield hotel?
Prices for hotels in Sheffield often vary, but you can find a great deal from $74 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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