Sheffield hotels from HK$665

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15 Nov - 16 Nov
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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 HK$1,043
HK$1,165 total
includes taxes & fees
16 Nov - 17 Nov
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, (1002)
"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 HK$852
HK$952 total
includes taxes & fees
7 Dec - 8 Dec
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, (1003)
"Great place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
The price is HK$769
HK$859 total
includes taxes & fees
15 Dec - 16 Dec
The Yankee, Trademark Collection by Wyndham
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (799)
"Easy parking, great community spaces, beautiful decor! "
United States
Kerry
The price is HK$698
HK$780 total
includes taxes & fees
16 Nov - 17 Nov
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, (781)
"Place was great!"
United States
Benjamin
The price is HK$991
HK$1,216 total
includes taxes & fees
16 Nov - 17 Nov
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, (1002)
"Very friendly staff. "
United States
Pamela
The price is HK$971
HK$1,388 total
includes taxes & fees
16 Nov - 17 Nov
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, (756)
"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, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1001)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is HK$1,077
HK$1,551 total
includes taxes & fees
15 Dec - 16 Dec
The Red Lion Inn
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 HK$1,055
HK$1,182 total
includes taxes & fees
16 Nov - 17 Nov
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)
"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
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, (58)
"Room was far from spotless but overall good and nice breakfast. "
United States
Hannah
The price is HK$852
HK$952 total
includes taxes & fees
16 Dec - 17 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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, (692)
"Solid location, great room, good breakfast. Fair Price. Been 3 different times and look forward to returning again "
United States
Jamie
The price is HK$831
HK$929 total
includes taxes & fees
20 Nov - 21 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (372)
"We LOVED our mini getaway at the Chambery Inn. The room was gorgeous, spacious, and very comfortable. The fireplace couldn't have been easier to operate. The jetted tubs were divine with plenty of hot water the towel warmer was a nice bonus. The room was fully stocked with glassware and a corkscrew which was appreciated. We look forward to coming back"
United States
Samuel
Chambery 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 HK$1,111
HK$1,241 total
includes taxes & fees
19 Nov - 20 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (157)
"Very good breakfast.excellent waiter.love the atmosphere."
United States
Marc
The price is HK$1,239
HK$1,425 total
includes taxes & fees
17 Nov - 18 Nov
Blackberry River Inn
Egyptian cotton sheets, premium bedding, down duvets, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
9.4 out of 10, Exceptional, (13)
"Prospect was a wonderful stay with very friendly staff. The property is very well maintained. We had a great time with the all the lake activities. Would definitely recommend for a quick getaway "
United States
Andy
The price is HK$2,002
HK$2,496 total
includes taxes & fees
30 Nov - 1 Dec
Prospect 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 HK$1,866
HK$2,111 total
includes taxes & fees
16 Nov - 17 Nov
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, (153)
"Great scenic location for hiking, etc Property, rooms and hosts are wonderful."
United States
Paul
The price is HK$1,644
HK$1,891 total
includes taxes & fees
24 Nov - 25 Nov
Cornwall Inn and Lodge
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
9.2 out of 10, Wonderful, (586)
"Fabulous place"
United States
Mary
The price is HK$917
HK$1,025 total
includes taxes & fees
14 Dec - 15 Dec
Courtyard by Marriott Lenox Berkshires
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, (410)
"Peaceful area and great staff; Thank you for the service and experience "
United States
Andre
The price is HK$816
HK$938 total
includes taxes & fees
23 Nov - 24 Nov
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

Drury Preserve

You can take time to visit Drury Preserve during your travels to Sheffield. Make some time to visit the casinos while you're in the area.
See properties

Ashley House

You can learn about the history of Sheffield when you stop by Ashley House. 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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Great stay!"
Ann 1-night trip
Posted 20 hours ago
The Yankee, Trademark Collection by Wyndham

More cheap stays in Sheffield

Quality Inn

Quality Inn

372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is HK$654 per night from 7 Dec to 8 Dec
HK$654
HK$730 total
7 Dec - 8 Dec
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)

Hotels in Sheffield with star-rating

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 traveller data. This B&B offers free breakfast and free parking. Two other options 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 holiday rentals that Sheffield has to offer?
Antique Farmhouse Totally Restored: This highly rated holiday home rental in Sheffield is located in a rural location, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. 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 reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If your reservation is non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.
What are some accommodation options with pools in Sheffield?
Berkshire Mountain Lodge: Offers free self parking, an indoor pool and complimentary wireless Internet access. The Red Lion Inn and The Yankee, Trademark Collection by Wyndham are a couple of other choices that feature an on-site 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 34 hotels and other accommodation options to choose from. Find out more about Sheffield.
What are the top places to visit in Sheffield?
Favourite places to visit include Housatonic River, Magnolia Bluffs Casino and Mount Everett State Reservation. A couple of additional sights to add to your itinerary are Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary. Take a look at what more there is to see and do in Expedia's Sheffield guide.
What's the seasonal weather like in Sheffield?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Sheffield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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