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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, (43 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
$148 nightly
The price is $166
Apr 15 - Apr 16
Total with taxes and fees
Wilder House Berkshires

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (60 reviews)
"Comfortable stay "
United States
Paul
$129 nightly
The price is $145
Mar 28 - Mar 29
Total with taxes and fees
Becket Motel

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (172 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
$158 nightly
The price is $182
Mar 30 - Mar 31
Total with taxes and fees
Blackberry River Inn

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.4 out of 10, Exceptional, (136 reviews)
"Beautiful property and rooms."
United States
Kara
$206 nightly
The price is $226
Mar 29 - Mar 30
Total with taxes and fees
Gedney Farm

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
$336 nightly
The price is $368
Mar 29 - Mar 30
Total with taxes and fees
The Old Inn On The Green

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (416 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
$105 nightly
The price is $121
Mar 29 - Mar 30
Total with taxes and fees
Locust Tree Bed and Breakfast LLC

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (83 reviews)
"Checkin was easy, room was clean and comfortable "
United States
Greg
$130 nightly
The price is $150
Mar 28 - Mar 29
Total with taxes and fees
Hitching Post Country Motel

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,001 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
$84 nightly
The price is $94
Apr 13 - Apr 14
Total with taxes and fees
Quality Inn Lee - Lenox South

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
"owners was nice, room was clean"
United States
tom
$95 nightly
The price is $106
Mar 28 - Mar 29
Total with taxes and fees
Sunset Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
$190 nightly
The price is $212
Mar 29 - Mar 30
Total with taxes and fees
Chambery Inn

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (659 reviews)
"Good to stay. "
United States
Ibinabo
$67 nightly
The price is $75
Apr 12 - Apr 13
Total with taxes and fees
Econo Lodge Lee - Great Barrington

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (157 reviews)
"We stay here frequently…always super clean and the inn keepers are very kind."
United States
Tracy
$212 nightly
The price is $243
Mar 28 - Mar 29
Total with taxes and fees
Cornwall Inn and Lodge

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
$329 nightly
The price is $367
Mar 28 - Mar 29
Total with taxes and fees
Devonfield Inn B&B

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, (1,001 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
$94 nightly
The price is $105
Apr 6 - Apr 7
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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, (858 reviews)
"Great place to enjoy with the whole family!!!"
United States
Elizabeth
$130 nightly
The price is $145
Mar 30 - Mar 31
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (295 reviews)
"Friendly staff, great location, beautiful views, cozy room."
United States
Elizabeth
$151 nightly
The price is $169
Mar 28 - Mar 29
Total with taxes and fees
Lakehouse Inn

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
$238 nightly
The price is $266
Apr 3 - Apr 4
Total with taxes and fees
The Inn at Stockbridge

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (87 reviews)
"New hotel clean and nice. Heated pool and hot tub a bonus. Timely breakfast for early departures- great on demand coffee. Added bonus they have a car charger."
United States
Charline
$132 nightly
The price is $147
Apr 6 - Apr 7
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (673 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
$139 nightly
The price is $155
Mar 29 - Mar 30
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (839 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
$79 nightly
The price is $88
Mar 28 - Mar 29
Total with taxes and fees
Howard Johnson by Wyndham Lenox
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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

  • Outdoor Adventures: Sheffield is a haven for outdoor enthusiasts with options for skiing, hiking, and exploring scenic landscapes.
  • Stunning Berkshire Hills: Experience breathtaking views and natural beauty in the enchanting Berkshire Hills.
  • Cultural Experiences: Discover local art galleries that showcase the region's creativity and charm.
  • Family-Friendly Atmosphere: Sheffield offers a welcoming environment perfect for families and adventure seekers.
  • Diverse Accommodations: Choose from cozy agritourism spots to charming bed & breakfasts for a unique lodging experience.

Find great hotels near Sheffield

Discover the charm of Sheffield, Massachusetts, where a variety of lodging options await you. From cozy agritourism properties to inviting bed & breakfasts, Sheffield offers accommodations that cater to families, adventure seekers, and pet lovers alike. Whether you’re looking for the best hotels or a detailed hotel map, you’ll find the perfect place to unwind and enjoy the scenic beauty of this quaint New England town.

  • 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 boasts a guest rating of 9.0, making it an ideal choice for families and adventure seekers. Located 12 miles from Sheffield, the resort offers easy access to skiing and outdoor activities. Guests can enjoy a range of on-site amenities including adventure sports, a playground for children, and an arcade game room. With activities like hiking, snowboarding, and mini-golf available, this resort is perfect for creating unforgettable family memories.
  • Quality Inn Great Barrington: A budget-friendly option with a guest rating of 8.4, the Quality Inn Great Barrington is situated 6 miles from Sheffield. This hotel caters to both adventure enthusiasts and business travelers, providing easy access to thrilling activities such as snowboarding, hiking, and cross-country skiing. Guests appreciate the comfortable accommodations and convenient amenities that make it a practical choice for their stay, ensuring a pleasant experience without breaking the bank.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: With a guest rating of 8.8, this budget-friendly hotel is located 7 miles from Sheffield and is particularly well-suited for business travelers. The Holiday Inn Express offers modern accommodations and essential amenities designed for a hassle-free experience. Guests can enjoy complimentary breakfast, Wi-Fi, and a fitness center, making it a convenient base for exploring the area while staying productive during their trip.

Where to stay near Sheffield

Sheffield, Massachusetts, offers a perfect blend of outdoor adventure and historical charm. Experience the enchanting Berkshire Hills, where you can ski or hike amidst stunning scenery. Explore local art galleries showcasing the region's creativity and unwind in the friendly atmosphere of this family-friendly destination. Whether you're seeking a romantic getaway or a relaxing retreat, Sheffield and its surrounding areas promise unforgettable memories.

  • Great Barrington: Situated a mere 6 miles from Sheffield, Great Barrington is a vibrant town known for its outdoor adventure and sports experiences. This charming location attracts visitors year-round, with peak travel occurring between June and August. Guests can enjoy skiing and various activities at the nearby ski fields and resorts, perfect for thrill-seekers. The town is surrounded by stunning landscapes, including picturesque lakes and majestic mountains, and offers access to a national state park, making it an ideal spot for nature lovers and outdoor enthusiasts alike.
  • The Berkshires: Located 11 miles from Sheffield, The Berkshires is a beautifully scenic region that captivates travelers with its stunning natural beauty. Peak visitation occurs from June to August, as people flock to experience its outdoor adventures and breathtaking scenery. Offering various ski resorts and fields, The Berkshires is perfect for winter sports lovers. The area is also home to serene lakes and majestic mountains, along with event venues hosting various conferences and cultural gatherings, ensuring that there’s always something exciting happening.
  • South Egremont: Just 5 miles from Sheffield, South Egremont is a quaint town that offers a wealth of outdoor activities and sports experiences. Similar to its neighbors, it sees peak visitation during the summer months from June to August. The area is popular for skiing, with several ski fields and resorts nearby. Visitors can explore the beautiful landscapes, including tranquil lakes and the scenic national state park, all set against the backdrop of stunning mountains, making South Egremont a perfect destination for those seeking adventure and relaxation in nature.

Things to do in Sheffield

Sheffield, Massachusetts, is perfect for outdoor enthusiasts seeking adventure and winter sports. Popular activities include skiing at local resorts and exploring scenic ski fields. Additionally, Sheffield offers great options for day trips, allowing visitors to experience the natural beauty of the area. Whether you're hitting the slopes or enjoying the picturesque landscape, Sheffield promises a memorable vacation.

Shopping

In Sheffield, you can shop at local gift shops for unique souvenirs. If you're up for a drive, check out the Berkshire Mall in nearby Lanesborough, where you'll find a variety of retail stores and dining options to complement your shopping experience.

Recreation

The Kripalu Center for Yoga & Health offers transformative wellness retreats with yoga classes, meditation, and healthy cuisine. Enjoy scenic hikes in the surrounding Berkshire Mountains for rejuvenation. Explore the peaceful tranquility of the nearby Berkshire Botanical Garden, featuring stunning landscapes and seasonal blooms to enhance your relaxation experience.

Adventure

Experience the beauty of nature at Beartown State Forest, where you can hike scenic trails and enjoy picturesque views. For thrilling outdoor fun, try kayaking on the Housatonic River, offering a perfect mix of adventure and relaxation amidst stunning landscapes.

Nightlife

In Sheffield, Massachusetts, the nightlife is cozy and inviting, with local pubs like the Sheffield Sports Bar offering live music and craft beers. Enjoy a relaxed evening at the quaint Berkshire Mountain Distillers, where you can sample artisanal spirits in a charming atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Sheffield

  • 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 options based on your budget, desired location, and the type of hotel you prefer. 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 hotel stay in Sheffield with your flights and activities by booking a package through Expedia.

Find the best attractions in and around Sheffield

Sheffield, Massachusetts, is perfect for outdoor enthusiasts seeking adventure and eco-friendly experiences. Popular attractions include nearby state parks, nature reserves, and picturesque lakes, providing ample opportunities for skiing and outdoor activities. Whether you’re looking to hike, fish, or simply enjoy the natural beauty, Sheffield offers a variety of experiences that cater to all types of travelers eager to explore its stunning landscapes.

  • Ashley House: Step into history at the Ashley House, a captivating museum that showcases the rich cultural heritage of Sheffield. With its charming architecture and engaging exhibits, it offers a unique glimpse into the past, making it a perfect stop for history enthusiasts.
  • Taconic State Park: Experience the great outdoors at Taconic State Park, located just 8 miles from Sheffield. Known for its stunning scenery, this park is ideal for hiking, picnicking, and exploring nature's beauty. Adventure awaits around every corner.
  • Housatonic River: Just 6 miles away, the Housatonic River offers serene views and outdoor activities. Enjoy fishing, kayaking, or simply relaxing by the water's edge while soaking in the picturesque landscape.

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

For travelers heading to Sheffield, Massachusetts, there are several major airports to consider. New York's LaGuardia Airport (LGA) is 96 miles away, with nearby hotels like The Plaza and The Pierre, both offering convenient airport shuttle services. Hartford’s Bradley International Airport (BDL) is 37 miles from Sheffield, featuring hotels such as the DoubleTree by Hilton and Simsbury 1820 House, also providing easy access to the airport. ALBany International Airport (ALB), located 50 miles away, has options like The Landing Hotel and DoubleTree by Hilton, all accessible from the airport. Each airport provides various transportation services to ensure a smooth journey to Sheffield.

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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