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

Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished
Wilder House Berkshires

Wilder House Berkshires

2.0 star property
Sheffield
9.8 out of 10, Exceptional, (38)
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "
United States
Allison
The price is ￥22,429
￥25,054 total
includes taxes & fees
Dec 9 - Dec 10
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
Lee
9.0 out of 10, Wonderful, (1006)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is ￥15,267
￥17,053 total
includes taxes & fees
Dec 22 - Dec 23
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1014)
"Great stay!"
United States
Ann
The price is ￥9,719
￥10,856 total
includes taxes & fees
Dec 14 - Dec 15
The Yankee, Trademark Collection by Wyndham
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (806)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is ￥17,057
￥19,053 total
includes taxes & fees
Dec 8 - Dec 9
Berkshires Untold
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
South Lee
9.0 out of 10, Wonderful, (794)
"Place was great!"
United States
Benjamin
The price is ￥16,567
￥20,678 total
includes taxes & fees
Dec 8 - Dec 9
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1000)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is ￥22,116
￥30,809 total
includes taxes & fees
Dec 21 - Dec 22
The Cornell Inn, Lenox & The Berkshires
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1004)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is ￥25,188
￥35,112 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Red Lion Inn
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (776)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Lobby sitting area
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, (64)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is ￥14,187
￥15,847 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Dinner served, American cuisine
the Alander

the Alander

2.5 star property
Copake
9.0 out of 10, Wonderful, (184)
"Very nice clean place in a beautiful area. "
United States
Wayne
The price is ￥21,778
￥24,391 total
includes taxes & fees
Dec 3 - Dec 4
the Alander
Double Room | Egyptian cotton sheets, premium bedding, memory foam beds, desk
The Brooks Motel

The Brooks Motel

2.0 star property
Hillsdale
7.6 out of 10, Good, (117)
"Yes everything was perfect, just had a little trouble getting the WIFI for the TV set up! "
United States
Zenovia
The Brooks Motel
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (162)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is ￥25,566
￥29,401 total
includes taxes & fees
Dec 8 - Dec 9
Blackberry River Inn
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Exterior
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, (702)
"Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. "
United States
Tabitha
The price is ￥16,645
￥18,592 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
9.2 out of 10, Wonderful, (588)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is ￥21,001
￥23,458 total
includes taxes & fees
Dec 10 - Dec 11
Courtyard by Marriott Lenox Berkshires
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"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 ￥40,446
￥50,391 total
includes taxes & fees
Dec 3 - Dec 4
Prospect Berkshires
Lobby
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, (757)
"Clean room, very courteous staff "
United States
Thomas
The price is ￥23,490
￥26,238 total
includes taxes & fees
Dec 8 - Dec 9
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Free daily continental breakfast
Inn at Pine Plains

Inn at Pine Plains

3.5 star property
Pine Plains
9.8 out of 10, Exceptional, (300)
"Great stay"
United Kingdom
Katherine
The price is ￥38,501
￥43,555 total
includes taxes & fees
Dec 3 - Dec 4
Inn at Pine Plains
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
Cornwall Inn and Lodge

Cornwall Inn and Lodge

3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (154)
"This inn was very quaint and welcoming. It was a nice inn for the value. "
United States
Jacqueline
The price is ￥32,916
￥37,853 total
includes taxes & fees
Dec 3 - Dec 4
Cornwall Inn and Lodge
Porch
Interlaken Inn & Resort

Interlaken Inn & Resort

3.5 star property
Lakeville
8.2 out of 10, Very Good, (270)
"The staff is courteous and accommodating especially the restaurant staff."
United States
Christian
The price is ￥32,769
￥37,684 total
includes taxes & fees
Dec 3 - Dec 4
Interlaken Inn & Resort
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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Thom Reed UFO Monument Park

Explore the great outdoors at Thom Reed UFO Monument Park, a lovely green space in 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

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Great stay, great breakfast"
Peter 1-night trip
Posted 2 days ago
Hampton Inn & Suites Berkshires-Lenox

More cheap stays in Sheffield

Quality Inn

Quality Inn

170 Housatonic Street Lee MA
The price is ￥14,413 per night from Dec 21 to Dec 22
￥14,413
￥16,099 total
Dec 21 - Dec 22
includes taxes & fees
8.2/10 Very Good! (1,003 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 The Red Lion Inn. 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: Provides free self parking, an indoor pool, and complimentary wireless internet access. The Red Lion Inn and Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG 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 34 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 Three Mile Pond Wildlife Management Area. A couple of additional sights to add to your agenda are Mount Everett State Reservation and Thom Reed UFO Monument Park. 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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