FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

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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, (56 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is CA $209
CA $234 total
includes taxes & fees
Jun 24 - Jun 25
Wilder House Berkshires

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (997 reviews)
"The staff was very helpful. It was very clean and the bed was comfortable. We would stay there again."
United States
Andrew
The price is CA $199
CA $253 total
includes taxes & fees
Jul 23 - Jul 24
Berkshire Mountain Lodge

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is CA $203
CA $226 total
includes taxes & fees
Jul 7 - Jul 8
The Yankee Inn

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,012 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is CA $154
CA $172 total
includes taxes & fees
Jun 24 - Jun 25
Quality Inn Great Barrington

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (424 reviews)
"Below average B&B"
United States
Larry
The price is CA $149
CA $171 total
includes taxes & fees
Jul 1 - Jul 2
Locust Tree Bed and Breakfast LLC

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, (778 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is CA $211
CA $236 total
includes taxes & fees
Jul 1 - Jul 2
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, (873 reviews)
"I was pleasantly surprised how clean,spacious,quiet and comfortable the room was ( two queens) Loved the place."
United States
Yekaterina
The price is CA $109
CA $122 total
includes taxes & fees
Jun 24 - Jun 25
Monument Mountain Motel

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (187 reviews)
"beautiful inn"
United States
Maura
The price is CA $206
CA $237 total
includes taxes & fees
Jul 6 - Jul 7
Blackberry River Inn

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (228 reviews)
"It’s a wonderful place to rest for a while. it has all you need, everything it’s in good conditions also it’s near of many activities like hiking."
United States
Daniel
The price is CA $241
CA $269 total
includes taxes & fees
Jul 7 - Jul 8
the Alander

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (165 reviews)
"A charming stopover on our weekend travels. Small, quiet and lovely. Nice conversation with the host over breakfast too."
United States
Janice
The price is CA $308
CA $354 total
includes taxes & fees
Jul 5 - Jul 6
Cornwall Inn and Lodge

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (587 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is CA $112
CA $125 total
includes taxes & fees
Jun 24 - Jun 25
Travelodge by Wyndham Great Barrington Berkshires

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (90 reviews)
"A little dated but clean. A room for the night for when I race at lime rock"
United States
William
The price is CA $184
CA $212 total
includes taxes & fees
Jul 1 - Jul 2
Hitching Post Country Motel

The Whitlock

The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (312 reviews)
"A beautiful old inn in the heart of a lovely old town."
United States
Linda
The price is CA $219
CA $245 total
includes taxes & fees
Jul 7 - Jul 8
The Whitlock

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,003 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is CA $200
CA $223 total
includes taxes & fees
Jul 7 - Jul 8
Quality Inn Lee - Lenox South

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (472 reviews)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is CA $96
CA $107 total
includes taxes & fees
Jul 1 - Jul 2
Berkshire Travel Lodge

The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (139 reviews)
"Nice "
United States
Daljit
The price is CA $157
CA $176 total
includes taxes & fees
Jun 24 - Jun 25
The Brooks Motel

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (227 reviews)
"Very clean. Updated "
United States
jennifer
The price is CA $158
CA $177 total
includes taxes & fees
Jun 24 - Jun 25
Chatham Travel Lodge

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (787 reviews)
"Dawn was super helpful in getting us checked in."
United States
Kristen
The price is CA $282
CA $315 total
includes taxes & fees
Jun 24 - Jun 25
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (871 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is CA $140
CA $157 total
includes taxes & fees
Jun 24 - Jun 25
Howard Johnson by Wyndham Lenox

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.6 out of 10, Excellent, (29 reviews)
"We had a beautiful experience, staff was very accommodating."
United States
Bernadette
The price is CA $352
CA $398 total
includes taxes & fees
Jul 5 - Jul 6
The Millerton 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

  • Outdoor Adventures: Sheffield is a haven for outdoor enthusiasts, offering activities like skiing, hiking, and exploring picturesque lakes and national parks.
  • Historical Charm: The town boasts a rich historical background, presenting visitors with charming architecture and a friendly atmosphere.
  • Family-Friendly Activities: Sheffield offers diverse attractions suitable for families, ensuring fun for travellers of all ages.
  • Scenic Beauty: Enjoy the stunning natural landscapes and serene scenery that Sheffield has to offer.
  • Comfortable Accommodations: A variety of lodging options cater to different preferences, from pet-friendly to adventure-filled stays.

Find great hotels near Sheffield

Discover a charming getaway in Sheffield, Massachusetts, where a variety of accommodations await to cater to every traveller's desires. Whether you're seeking a pet-friendly retreat, family-friendly services, or an adventure-filled experience, Sheffield's hotels offer comfort and convenience. Explore the best options available to ensure a memorable stay in this picturesque town.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Experience a family-friendly adventure at the 3.5-star Holiday Inn Club Vacations Oak n’ Spruce Resort, rated 9.0 by guests. Located 19.3km from Sheffield, this resort is perfect for those seeking winter sports and outdoor activities. With amenities like ski lessons, snowboarding, and hiking, adventure awaits right at your doorstep. Families will appreciate the onsite mini-golf, arcade game room, and a playground for kids. This resort is designed to accommodate guests of all ages, making it an ideal choice for a fun-filled vacation.
  • Quality Inn Great Barrington: For budget-conscious travellers, the Quality Inn Great Barrington offers a cozy experience just 9.7km from Sheffield. With a guest rating of 8.4, this hotel is perfect for those seeking adventure or business travel. Guests can enjoy nearby activities such as snowshoeing, cross-country skiing, and snow tubing. The hotel provides a comfortable stay with essential amenities, ensuring a pleasant visit without breaking the bank. It’s an excellent base for exploring the Berkshires while keeping the focus on value and convenience.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Located 11.3km from Sheffield, the Holiday Inn Express Hotel & Suites Great Barrington is a budget-friendly option with a guest rating of 8.8. This hotel caters to business travellers while still providing a welcoming atmosphere for leisure guests. It features modern accommodations and essential amenities, making it an ideal choice for those who need to stay connected while on the go. Enjoy a comfortable night’s sleep and start your day with a complimentary breakfast before exploring the picturesque Berkshires.

Where to stay near Sheffield

Sheffield, Massachusetts, offers a delightful blend of outdoor adventures and rich historical charm. Whether you're skiing on nearby slopes or exploring the heart of Sheffield, you'll find the city’s friendly atmosphere inviting. Enjoy family-friendly activities, serene scenery, and romantic spots in the Sheffield city centre. Don't miss the opportunity to experience the luxury accommodations and vibrant neighborhoods that make Sheffield a perfect vacation destination for all types of travellers.

  • Great Barrington: Located 9.7km from Sheffield, Great Barrington is a charming city that attracts visitors year-round, particularly from June to August. Known for its outdoor adventures, the area is a haven for skiing enthusiasts, with numerous ski fields and resorts nearby. The picturesque landscape features stunning lakes and mountains, making it perfect for nature lovers. Don't miss the opportunity to explore the local national state park, where you can hike and enjoy the breathtaking scenery.
  • The Berkshires: Situated 17.7km from Sheffield, The Berkshires is renowned for its natural beauty and outdoor recreational activities. Visitors flock here during the summer months, but the area offers year-round attractions. With its diverse landscape, The Berkshires is ideal for skiing, hiking, and enjoying the serene lakes. Outdoor enthusiasts will appreciate the picturesque ski resorts and fields, while cultural aficionados can attend events at local conference venues that showcase the region's artistic flair.
  • South Egremont: Just 8.0km from Sheffield, South Egremont is a delightful city that offers a mix of adventure and relaxation. Like its neighbours, it experiences a peak in visitor numbers from June to August, drawing those eager to ski and explore the outdoors. The area is surrounded by beautiful lakes and mountains, providing a perfect backdrop for various activities. Outdoor enthusiasts can find ski resorts and fields nearby, making it an excellent destination for sports lovers seeking excitement in the great outdoors.

Things to do in Sheffield

Sheffield, Massachusetts, is perfect for outdoor enthusiasts seeking adventure and excitement. Visitors can enjoy thrilling ski experiences at local ski resorts and fields, as well as various outdoor activities. The area also boasts attractive city sights, beautiful golf courses, and numerous recreational facilities, making it an ideal destination for those looking to explore its natural beauty and enjoy a range of exciting rides.

Shopping

Sheffield offers charming local shops like the Sheffield General Store for unique gifts and souvenirs. If you're up for a drive, visit the Berkshire Mall in Lanesborough, about 24.1km away, where you can find a variety of retail stores and dining options.

Recreation

The Kripalu Centre for Yoga & Health offers transformative wellness retreats, featuring yoga classes, meditation, and healthy cuisine in a tranquil setting. Explore the beautiful Berkshire mountains on hiking trails or unwind at local spas for rejuvenating treatments, creating a perfect balance of relaxation and adventure.

Adventure

In Sheffield, explore the breathtaking landscapes of the Berkshires with hiking at Mount Everett State Reservation, where panoramic views await. Enjoy thrilling canoeing on the Housatonic River, or immerse yourself in nature at the nearby Bash Bish Falls for a refreshing adventure.

Nightlife

Experience Sheffield's charming nightlife at The Castle Street Café, where delicious local cuisine meets a relaxed vibe. For a lively evening, visit The Sheffield Inn, offering great drinks and live music, perfect for mingling with locals and fellow travellers alike.

*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 preferences, such as your budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly accommodations currently available. To find the best prices and offers, 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 through an Expedia package deal.

Find the best attractions in and around Sheffield

Sheffield, Massachusetts, is a fantastic destination for outdoor enthusiasts seeking adventure and eco-friendly experiences. With its stunning national parks, serene nature reserves, and picturesque lakes, visitors can indulge in various activities, from skiing to hiking. Whether you're looking for a thrilling outdoor vacation or a peaceful retreat in nature, Sheffield offers a diverse range of attractions that cater to all types of travellers.

  • Ashley House: Experience the rich cultural heritage of Sheffield at the Ashley House museum. This historic site offers a glimpse into the past with its beautifully preserved architecture and engaging exhibits that reflect local history and culture.
  • Taconic State Park: Just 12.9km from Sheffield, Taconic State Park is perfect for adventure enthusiasts. Enjoy breathtaking scenery, hiking trails, and outdoor activities that allow you to immerse yourself in the stunning natural beauty of the region.
  • Housatonic River: Located 9.7km from Sheffield, the Housatonic River offers picturesque views and opportunities for outdoor recreation. Whether kayaking or simply enjoying a peaceful walk along the river, you’ll find a connection with nature here.

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

If you're planning a trip to Sheffield, Massachusetts, there are several major airports you can consider. New York's LaGuardia Airport (LGA) is 154.5km away, with luxury options like The Plaza and The Pierre, both 8.0km from the airport, offering shuttle services. Hartford's Bradley International Airport (BDL) is closer at 59.5km, with the DoubleTree by Hilton just 1.6km away, providing convenient access. ALBany International Airport (ALB), located 80.5km from Sheffield, has several good hotels, including The Landing Hotel at Rivers Casino, 12.9km from the airport. These airports offer a range of transportation options to ensure a smooth journey to your destination.

Frequently asked questions

What is the best area to stay in Sheffield?
The best area to stay in Sheffield, Massachusetts, is the town centre, particularly around Main Street (Route 7).

Sheffield's town centre is a pleasant and convenient base for exploring the Southern Berkshires. Main Street is where you'll find a selection of antique shops, local eateries, and a few small galleries. The town maintains a relaxed, rural character, making it easy to unwind.

Couples looking for a tranquil getaway will appreciate the quiet charm of Sheffield. Many accommodations here offer a peaceful setting, often with views of the surrounding hills, great for relaxing after a day of exploring the region's art and nature. It's also a great base for visiting nearby towns such as Great Barrington.

For those interested in outdoor activities and nature, staying in or just outside the town centre provides easy access to local hiking trails and scenic drives.
What are the best hotels in Sheffield that travellers recommend?
For a highly recommended hotel in Sheffield, Massachusetts, consider the Wilder House Berkshires.

The Wilder House Berkshires, with an outstanding 9.8 rating, is praised by guests for its comfortable and clean rooms. Travellers particularly enjoy the great and delicious complimentary cooked breakfast. The hotel also offers premium bedding, air conditioning, and free self-parking, ensuring a convenient and pleasant stay.
What are the best family hotels in Sheffield?
For families travelling to Sheffield, the Wilder House Berkshires is an excellent choice.

This highly-rated accommodation, with an impressive 9.8 review score, offers a welcoming stay for families. Guests consistently praise the comfortable and clean rooms, ensuring a pleasant environment for everyone. A significant advantage for families is the complimentary breakfast, including cooked options, which guests describe as great and delicious. Free toiletries, free WiFi, and free self-parking add to the convenience and value. The availability of a free crib further highlights its family-friendly focus, making it easier for parents travelling with infants.
What hotels in Sheffield offer free breakfast?
For hotels in Sheffield that provide complimentary breakfast, the Wilder House Berkshires is an excellent option.

This highly-rated property, with an impressive 9.8 review score, offers both free breakfast and free cooked breakfast, which guests consistently describe as great and delicious. The rooms are noted for being comfortable and clean, and the hotel also provides free WiFi, free self-parking, and premium bedding. Additionally, it is conveniently located just 10.2 km from the Housatonic River.
What are the best budget hotels in Sheffield?
For a great budget hotel in Sheffield, consider the Wilder House Berkshires.

The Wilder House Berkshires has an exceptional review rating of 9.8. Guests consistently mention the comfortable and clean rooms, along with the great and delicious breakfast. This hotel provides a range of complimentary amenities, including free cooked breakfast, free toiletries, free WiFi, and free self-parking. The rooms also feature premium bedding and air conditioning for added comfort. It is located approximately 10.2 km from 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, depends on your preferences for outdoor activities and the region's natural beauty.

For those who enjoy warm weather and outdoor adventures, the summer months from June to August are ideal. The Berkshires are lush and green during this period, superb for hiking, cycling, and enjoying the numerous lakes and rivers. You'll find many local farms offering fresh produce, and outdoor events are plentiful.

If you're particularly interested in the stunning autumn foliage, late September through October is the most picturesque time to visit. The hillsides transform into a spectacular display of reds, oranges, and yellows, making it superb for scenic drives and photography. This period is very popular, so booking accommodation well in advance is recommended.

For winter sports enthusiasts, December through March offers opportunities for skiing, snowboarding, and snowshoeing at nearby resorts. The landscape is often covered in snow, creating a serene and beautiful setting, though some smaller shops and attractions might have reduced hours.

Spring, from April to May, sees the awakening of the landscape with blooming flowers and budding trees.
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?
Members always get our best prices. Find our best Sheffield hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
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 CA $122 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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