Sheffield Hotels

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Nov 20 - Nov 21
Tomorrow
Nov 21 - Nov 22
This weekend
Nov 21 - Nov 23
Next weekend
Nov 28 - Nov 30

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Top 10 trending Sheffield hotels

1 bedroom, premium bedding, individually decorated
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 P8,486
P9,479 total
includes taxes & fees
Nov 23 - Nov 24
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, (1000)
"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 P6,261
P6,994 total
includes taxes & fees
Dec 11 - Dec 12
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, (1005)
"Great stay!"
United States
Ann
The price is P5,360
P5,987 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, (800)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is P5,460
P6,098 total
includes taxes & fees
Nov 23 - Nov 24
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, (786)
"Place was great!"
United States
Benjamin
The price is P6,276
P7,833 total
includes taxes & fees
Nov 24 - Nov 25
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, (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 P7,590
P10,782 total
includes taxes & fees
Nov 21 - Nov 22
The Cornell Inn, Lenox & The Berkshires
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (761)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is P8,780
P12,441 total
includes taxes & fees
Dec 15 - Dec 16
The Red Lion Inn
Dinner served, American cuisine
the Alander

the Alander

2.5 star property
Copake
9.0 out of 10, Wonderful, (182)
"Very nice clean place in a beautiful area. "
United States
Wayne
The price is P7,071
P7,920 total
includes taxes & fees
Nov 24 - Nov 25
the Alander
Egyptian cotton sheets, premium bedding, memory foam beds, desk
The Brooks Motel

The Brooks Motel

2.0 star property
Hillsdale
7.4 out of 10, Good, (116)
"Everything was lovely, thanks. Small note: the toilet seat needs a bolt on one side. Otherwise everything was great! Thx"
United States
Savannah
The Brooks Motel
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (60)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is P6,218
P6,946 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (372)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (159)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is P9,685
P11,138 total
includes taxes & fees
Dec 1 - Dec 2
Blackberry River Inn
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, (754)
"Clean room, very courteous staff "
United States
Thomas
The price is P8,436
P9,423 total
includes taxes & fees
Nov 25 - Nov 26
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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, (695)
"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 P6,600
P7,372 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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, (153)
"This inn was very quaint and welcoming. It was a nice inn for the value. "
United States
Jacqueline
The price is P12,469
P14,340 total
includes taxes & fees
Dec 15 - Dec 16
Cornwall Inn and Lodge
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
9.6 out of 10, Exceptional, (14)
"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 P15,322
P19,089 total
includes taxes & fees
Nov 24 - Nov 25
Prospect Berkshires
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
9.2 out of 10, Wonderful, (586)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is P6,725
P7,512 total
includes taxes & fees
Dec 21 - Dec 22
Courtyard by Marriott 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, (299)
"Great stay"
United Kingdom
Katherine
The price is P14,585
P16,499 total
includes taxes & fees
Nov 24 - Nov 25
Inn at Pine Plains
Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

3.0 star property
East Canaan
9.0 out of 10, Wonderful, (411)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is P6,188
P7,116 total
includes taxes & fees
Nov 21 - Nov 22
Locust Tree Bed and Breakfast LLC
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

Bartholomews Cobble

Explore the great outdoors at Bartholomews Cobble, a lovely green space in Sheffield. Make some time to visit the casinos while you're in the area.
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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

Blackberry River Inn

Blackberry River Inn

10/10 Excellent
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
Paulina 1-night trip
Posted 3 days ago
Blackberry River Inn

More cheap stays in Sheffield

Quality Inn

Quality Inn

170 Housatonic Street Lee MA
The price is P5,460 per night from Dec 7 to Dec 8
P5,460
P6,099 total
Dec 7 - Dec 8
includes taxes & fees
8.2/10 Very Good! (1,000 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.
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.
What are some accommodations with pools in Sheffield?
Berkshire Mountain Lodge: Offers 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'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 33 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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