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Compare 1,267 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated
Wilder House Berkshires
Wilder House Berkshires
2.0 star property
9.8 out of 10, Exceptional, (37)
"Highly recommend this beautiful bed & breakfast! The room was wonderful and overlooked the property, the breakfast was delicious, and the hospitality was amazing. I had a fantastic stay, and will definitely stay at The Wilder House again when I'm in the area."
United States
Marina
The price is ￥22,754
￥25,416 total
includes taxes & fees
Nov 5 - Nov 6
Wilder House Berkshires
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1002)
"Great Indian restaurant in the hotel!"
United States
Chris
The price is ￥16,220
￥18,118 total
includes taxes & fees
Nov 6 - Nov 7
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Interior
Berkshires Untold
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (787)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is ￥14,144
￥15,799 total
includes taxes & fees
Nov 2 - Nov 3
Berkshires Untold
Exterior
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1023)
"Fresh breakfast menu, clean and great location."
United States
Gail
The price is ￥16,350
￥18,263 total
includes taxes & fees
Nov 2 - Nov 3
The Yankee, Trademark Collection by Wyndham
Front of property
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1001)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is ￥19,662
￥27,931 total
includes taxes & fees
Nov 2 - Nov 3
The Cornell Inn, Lenox & The Berkshires
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (740)
"Great stay, perfect "
United States
Lawrence
Berkshire Mountain Lodge
Property amenity
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
9.0 out of 10, Wonderful, (773)
"We enjoyed our stay and will definitely be back."
United States
Howard
The price is ￥17,861
￥22,082 total
includes taxes & fees
Nov 11 - Nov 12
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Double Room | Egyptian cotton sheets, premium bedding, memory foam beds, desk
The Brooks Motel
The Brooks Motel
2.0 star property
7.6 out of 10, Good, (112)
"The room was very comfortable & clean. It had a really nice shower, which is very important for us when travelling. Thank you! See you again some time."
United States
Robert
The Brooks Motel
Outdoor pool, sun loungers
The Red Lion Inn
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1024)
"Picture perfect Inn"
United States
jeff
The price is ￥21,154
￥30,449 total
includes taxes & fees
Nov 13 - Nov 14
The Red Lion Inn
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
9.4 out of 10, Exceptional, (55)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
United States
Marti
The price is ￥18,209
￥20,340 total
includes taxes & fees
Dec 1 - Dec 2
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Dinner served, American cuisine
the Alander
the Alander
2.5 star property
9.0 out of 10, Wonderful, (178)
"Very nice clean place in a beautiful area. "
United States
Wayne
The price is ￥21,372
￥23,937 total
includes taxes & fees
Nov 3 - Nov 4
the Alander
Front of property
The Constance by the Lenox Collection
The Constance by the Lenox Collection
3.5 star property
8.4 out of 10, Very Good, (558)
"Everything was very nice. A very simple experience."
United States
Anthony
The price is ￥16,682
￥18,634 total
includes taxes & fees
Nov 3 - Nov 4
The Constance by the Lenox Collection
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8 out of 10, Excellent, (683)
"This motel was easy access right off the highway, super clean, and the staff was great. We would definitely stay here again. Breakfast options were good as well. "
United States
Tina
The price is ￥16,491
￥18,420 total
includes taxes & fees
Nov 11 - Nov 12
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.4 out of 10, Exceptional, (747)
"The property is very nice and the staff was extremely friendly and helpful."
United States
Greg
The price is ￥21,830
￥24,384 total
includes taxes & fees
Nov 5 - Nov 6
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Library
Blackberry River Inn
Blackberry River Inn
3.0 star property
9.4 out of 10, Exceptional, (151)
"Very good breakfast.excellent waiter.love the atmosphere."
United States
Marc
The price is ￥25,089
￥28,852 total
includes taxes & fees
Nov 3 - Nov 4
Blackberry River Inn
Front of property
Chambery Inn
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (371)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires
Prospect Berkshires
3.0 star property
9.4 out of 10, Exceptional, (12)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is ￥38,912
￥48,580 total
includes taxes & fees
Nov 9 - Nov 10
Prospect Berkshires
Exterior
Chatham Travel Lodge
Chatham Travel Lodge
2.5 star property
7.8 out of 10, Good, (208)
" Nice"
United States
Katherine
The price is ￥17,707
￥19,832 total
includes taxes & fees
Nov 10 - Nov 11
Chatham Travel Lodge
Terrace/patio
Locust Tree Bed and Breakfast LLC
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (409)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is ￥16,029
￥18,433 total
includes taxes & fees
Nov 1 - Nov 2
Locust Tree Bed and Breakfast LLC
Property amenity
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (584)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is ￥19,573
￥21,864 total
includes taxes & fees
Nov 23 - Nov 24
Courtyard by Marriott Lenox Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Sheffield attractions

Ashley House

You can learn about the history of Sheffield with a trip to Ashley House. Discover the area's breweries or seek out the hiking trails.
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Bartholomew's Cobble

You can take time to visit Bartholomew's Cobble during your travels to Sheffield. Make some time to visit the casinos while you're in the area.
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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.

See all hotels in Sheffield
FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

Top Sheffield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Clean room and very friendly staff. "
Michael 2-night trip
Posted 7 hours ago
The Red Lion Inn

More cheap stays in Sheffield

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
The price is ￥12,060 per night from Nov 1 to Nov 2
￥12,060
￥13,471 total
Nov 1 - Nov 2
includes taxes & fees
7.4/10 Good! (815 reviews)

Frequently asked questions

Where is the best place to stay in Sheffield?
Wilder House Berkshires is one of the top choices for your stay based on our traveler data. This B&B offers free breakfast and free parking. Other good choices for your trip to the area are Berkshire Mountain Lodge and Berkshires Untold. See all available top hotels, or vacation rentals in Sheffield.
What are some of the best vacation home rentals that Sheffield has to offer?
Antique Farmhouse Totally Restored: This highly rated vacation home rental in Sheffield is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. See all vacation rentals in Sheffield.
If I need to cancel my hotel reservation in Sheffield, will I receive a refund?
Yes! The majority of hotel room reservations are refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your check-in date. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.
Where can I learn more about changing or cancelling my trip to Sheffield?
To access more information about changing or cancelling your trip to Sheffield, go to https://www.expedia.com/service/.
What's the best place to stay near Ashley House?
Sheffield 1802 House is one of the top choices for your stay based on our traveler data, and this 3.5-star B&B offers free breakfast and free parking. It's located 3.2 mi (5.1 km) from Ashley House. Another good option is Locust Tree Bed and Breakfast, located 3.8 mi (6.2 km) away.
What about the best place to stay near Magnolia Bluffs Casino?
One of the top choices for your stay is Sheffield 1802 House, located 1.6 mi (2.6 km) from Magnolia Bluffs Casino, and this 3.5-star B&B offers free breakfast and free parking.
What are some accommodations with pools in Sheffield?
Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. The Red Lion Inn and Howard Johnson by Wyndham Lenox are a couple of other choices that offer an onsite pool. View all hotels with pools in Sheffield.
What is the best accommodation for staying close to Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
What's it like staying in Sheffield?
Visitors can enjoy all that Sheffield has to offer including the casinos and local tours. In Sheffield, there are 32 hotels and other accommodations to choose from. Find out more about Sheffield.
What should I see while I'm in Sheffield?
Favorite places to visit include Housatonic River, Magnolia Bluffs Casino, and Mount Everett State Reservation. A couple of additional sights to add to your agenda are Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary. Check out what more to see and do in Expedia's Sheffield guide.
What's the weather like in Sheffield?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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