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

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Jun 19 - Jun 21
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Jun 26 - Jun 28

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Our top choices for Sheffield hotels

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Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (53 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is ￥28,111
￥31,400 total
includes taxes & fees
Jun 22 - Jun 23
Wilder House Berkshires
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,013 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is ￥16,793
￥18,758 total
includes taxes & fees
Jun 15 - Jun 16
The Yankee Inn
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,001 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is ￥15,071
￥16,834 total
includes taxes & fees
Jun 17 - Jun 18
Quality Inn Great Barrington
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (106 reviews)
"Most comfortable hotel bed I've ever slept in"
United States
Matthew
The price is ￥22,434
￥25,059 total
includes taxes & fees
Jun 22 - Jun 23
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (461 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ￥21,966
￥24,097 total
includes taxes & fees
Jun 17 - Jun 18
Shaker Mill Inn
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (469 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 ￥10,526
￥11,790 total
includes taxes & fees
Jun 15 - Jun 16
Berkshire Travel Lodge
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (867 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 ￥12,330
￥13,774 total
includes taxes & fees
Jun 21 - Jun 22
Monument Mountain Motel
Lake view

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect!!"
United States
Grzegorz
The price is ￥22,882
￥25,559 total
includes taxes & fees
Jun 15 - Jun 16
Berkshire Lake Lodge
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (565 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is ￥14,101
￥15,751 total
includes taxes & fees
Jun 16 - Jun 17
The Little Lion
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (986 reviews)
"Great lobby and dining room atmosphere!"
United States
Carin
The price is ￥21,806
￥24,357 total
includes taxes & fees
Jun 18 - Jun 19
Berkshires Untold
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (867 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is ￥12,659
￥14,140 total
includes taxes & fees
Jun 15 - Jun 16
Howard Johnson by Wyndham Lenox
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (978 reviews)
"Very quiet and clean will book again"
United States
Sade
The price is ￥22,489
￥28,700 total
includes taxes & fees
Jul 13 - Jul 14
Berkshire Mountain Lodge
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,006 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is ￥21,160
￥23,636 total
includes taxes & fees
Jun 17 - Jun 18
Quality Inn Lee - Lenox South
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, (772 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is ￥21,953
￥24,522 total
includes taxes & fees
Jun 23 - Jun 24
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (420 reviews)
"Below average B&B"
United States
Larry
The price is ￥16,825
￥19,349 total
includes taxes & fees
Jun 17 - Jun 18
Locust Tree Bed and Breakfast LLC
In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (583 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 ￥12,659
￥14,140 total
includes taxes & fees
Jun 15 - Jun 16
Travelodge by Wyndham Great Barrington Berkshires
Free daily buffet breakfast

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,006 reviews)
"Good location and great breakfast."
United States
Linda
The price is ￥24,137
￥26,961 total
includes taxes & fees
Jun 25 - Jun 26
Hampton Inn & Suites Berkshires-Lenox
BBQ/picnic area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (7 reviews)
"Wonderful pet-friendly property in a fantastic location. Everything in the village is just a short walk away, making it easy to enjoy local shops, restaurants, and attractions."
United States
Leonardo
The price is ￥23,792
￥26,575 total
includes taxes & fees
Jun 15 - Jun 16
Hideaway Inn Lenox
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (186 reviews)
"beautiful inn"
United States
Maura
The price is ￥23,827
￥27,401 total
includes taxes & fees
Jun 22 - Jun 23
Blackberry River Inn
Restaurant

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (81 reviews)
"Excellent lodge, recommend."
United States
Jason
The price is ￥24,373
￥27,295 total
includes taxes & fees
Jun 25 - Jun 26
Little Cat Lodge
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

Magnolia Bluffs Casino

Why not roll the dice with a visit to Magnolia Bluffs Casino during your travels in Sheffield? Discover the area's breweries or seek out the hiking trails.
See properties

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

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

6/10 Okay
"Deep cleaning needs to be done and the hot tub was dirty. had to clean but it was a nice room. Owner very nice and he was sorry about the tub. It could have been the filters."
Susan 1-night trip
Posted 2 hours ago
Howard Johnson by Wyndham Lenox

More cheap stays in Sheffield

Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
The price is ￥15,071 per night from Jun 17 to Jun 18
￥15,071
￥16,834 total
Jun 17 - Jun 18
includes taxes & fees
8.6/10 Excellent! (1,001 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?
Luxury Private Estate in the Berkshires | Whitney by AvantStay: This Sheffield vacation home rental offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the foosball table in this rental home to help you unwind. Our travelers also rate Antique Farmhouse Totally Restored as a favorite home for rent in Sheffield. 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 Yankee Inn and The Red Lion Inn 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 Thom Reed UFO Monument Park. A couple of additional sights to add to your agenda are Lime Kiln Farm Wildlife Sanctuary and Three Mile Pond Wildlife Management Area. 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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