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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, (46 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is CA $250
CA $279 total
includes taxes & fees
May 11 - May 12
Wilder House Berkshires

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1,008 reviews)
"Very friendly staff and conviently located"
United States
Dawn
The price is CA $116
CA $129 total
includes taxes & fees
May 12 - May 13
Quality Inn Great Barrington

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (578 reviews)
"Clean"
United States
Brian
The price is CA $102
CA $114 total
includes taxes & fees
May 13 - May 14
Travelodge by Wyndham Great Barrington Berkshires

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is CA $122
CA $136 total
includes taxes & fees
May 10 - May 11
The Yankee Inn

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (417 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
The price is CA $143
CA $165 total
includes taxes & fees
May 15 - May 16
Locust Tree Bed and Breakfast LLC

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (849 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is CA $93
CA $104 total
includes taxes & fees
May 17 - May 18
Monument Mountain Motel

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (925 reviews)
"Spacious, clean, and the pool was warm and perfect for family swimming "
United States
Danielle
The price is CA $120
CA $164 total
includes taxes & fees
May 24 - May 25
Berkshire Mountain Lodge

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (853 reviews)
"Great value"
United States
Ralph
The price is CA $108
CA $120 total
includes taxes & fees
May 10 - May 11
Howard Johnson by Wyndham Lenox

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (932 reviews)
"Great stay!"
United States
Aditya
The price is CA $155
CA $173 total
includes taxes & fees
May 10 - May 11
Berkshires Untold

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is CA $82
CA $90 total
includes taxes & fees
May 26 - May 27
Pleasant Valley Motel West Stockbridge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is CA $228
CA $254 total
includes taxes & fees
May 25 - May 26
Element Lenox Berkshires

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,004 reviews)
"Great location "
United States
Edith
The price is CA $151
CA $168 total
includes taxes & fees
May 19 - May 20
Quality Inn Lee - Lenox South

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, (92 reviews)
"Room was clean, bed was comfortable, pool was nice, breakfast and coffee were good!"
United States
Haley
The price is CA $161
CA $180 total
includes taxes & fees
May 17 - May 18
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,005 reviews)
"Staff was friendly, room was clean and the beds were comfortable. Dog friendly also. Good breakfast selection. I would stay there again."
United States
Lillian
The price is CA $169
CA $188 total
includes taxes & fees
May 11 - May 12
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (453 reviews)
"Everything was excellent"
United States
Barbara
The price is CA $147
CA $161 total
includes taxes & fees
May 11 - May 12
Shaker Mill Inn

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (466 reviews)
"The breakfast was not diabetic friendly. They stated pet friendly but no place for dog to go to the bathroom. Had to walk dog through garbage . Cigarette butts all over very the place. Beds were terrible. My towels had clumps of black hair on them. Lotion and shampoos left in room were used not new ones. Will not go back"
United States
Stacy
The price is CA $90
CA $100 total
includes taxes & fees
May 11 - May 12
Berkshire Travel Lodge

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (663 reviews)
"Good to stay. "
United States
Ibinabo
The price is CA $87
CA $97 total
includes taxes & fees
May 25 - May 26
Econo Lodge Lee - Great Barrington

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (559 reviews)
"A nice safe and quiet place to stay. Park right in front of your door. My dog loved the large grass area. The room was large and the beds very comfortable. The heat was on when we arrived which was great . It was cold and snowy that day. I loved having the self check-in and check out. We plan on going back the next time we are in the area. "
United States
SUSAN
The price is CA $150
CA $168 total
includes taxes & fees
May 27 - May 28
The Little Lion

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (177 reviews)
"Charming, quiet, clean very clean with a beautiful dining room for breakfast and very respectful service."
United States
Mara
The price is CA $194
CA $223 total
includes taxes & fees
May 10 - May 11
Blackberry River Inn

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (219 reviews)
"Very clean. Updated "
United States
jennifer
The price is CA $153
CA $171 total
includes taxes & fees
Jun 6 - Jun 7
Chatham Travel Lodge
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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

Recent Reviews in Sheffield

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 $104 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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