Sheffield Hotels

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11 Oct - 12 Oct
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12 Oct - 13 Oct
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17 Oct - 19 Oct
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Top 10 trending Sheffield hotels

Wilder House Berkshires
Wilder House Berkshires Room 3

Wilder House Berkshires

2.0 star property
9.8 out of 10, Exceptional, (36)
"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."
The price is €166
includes taxes & fees
11 Nov - 12 Nov
Wilder House Berkshires
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1006)
"Great Indian restaurant in the hotel!"
The price is €102
includes taxes & fees
6 Nov - 7 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (754)
"Easy parking, great community spaces, beautiful decor! "
The price is €84
includes taxes & fees
2 Nov - 3 Nov
Berkshires Untold
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1004)
"Great location, very clean!"
The price is €129
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (751)
"The lodging was convenient to all the area attractions."
The price is €124
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1005)
"Very friendly staff. "
The price is €157
includes taxes & fees
28 Oct - 29 Oct
The Cornell Inn, Lenox & The Berkshires
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (688)
"Great stay, perfect "
The price is €109
includes taxes & fees
2 Nov - 3 Nov
Berkshire Mountain Lodge
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1007)
"great place have stayed several times, and hope to return."
The price is €182
includes taxes & fees
6 Nov - 7 Nov
The Red Lion Inn
The Brooks Motel
Double Room

The Brooks Motel

2.0 star property
7.6 out of 10, Good, (105)
"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."
The Brooks Motel
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby sitting area

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.4 out of 10, Exceptional, (52)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is €115
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
the Alander
American cuisine

the Alander

2.5 star property
9.0 out of 10, Wonderful, (170)
"Good location, clean and nice touches in the rooms (french press coffee pot and freshly ground coffee, Harney teas, Saratoga Spring water, and other nice amenities). The fire pits are a nice plus! "
The price is €154
includes taxes & fees
13 Oct - 14 Oct
the Alander
The Constance by the Lenox Collection
Front of property

The Constance by the Lenox Collection

3.5 star property
8.4 out of 10, Very good, (551)
"Very quiet and comfortable "
The price is €93
includes taxes & fees
3 Nov - 4 Nov
The Constance by the Lenox Collection
Chatham Travel Lodge
Exterior

Chatham Travel Lodge

2.5 star property
7.8 out of 10, Good, (202)
"Clean, comfortable room. Check in was easy."
The price is €112
includes taxes & fees
12 Oct - 13 Oct
Chatham Travel Lodge
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (142)
"Loved everything especially Lucas and Joe💟☮️"
The price is €163
includes taxes & fees
14 Oct - 15 Oct
Blackberry River Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lobby

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (743)
"The property is very nice and the staff was extremely friendly and helpful."
The price is €137
includes taxes & fees
6 Nov - 7 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (635)
"Easy check in"
The price is €60
includes taxes & fees
9 Nov - 10 Nov
Econo Lodge Lee - Great Barrington
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (406)
"Peaceful area and great staff; Thank you for the service and experience "
The price is €104
includes taxes & fees
14 Oct - 15 Oct
Locust Tree Bed and Breakfast LLC
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (576)
"The front desk, food service, and housekeeping staff were all very friendly. The room was immaculate as well. "
The price is €122
includes taxes & fees
9 Nov - 10 Nov
Courtyard by Marriott Lenox Berkshires
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (671)
"The staff was friendly and helpfull. The property was clean and functional."
The price is €99
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Prospect Berkshires
Egyptian cotton sheets, premium bedding, down duvets, minibar

Prospect Berkshires

3.0 star property
9.0 out of 10, Wonderful, (7)
"Gorgeous thoughtfully designed cabins with so many amenities/activities. Cliff house restaurant was delicious. Perfect getaway. "
The price is €310
includes taxes & fees
9 Nov - 10 Nov
Prospect 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 when you stop by 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.

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Top Sheffield Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"Easy parking, good air air-conditioning."
Carolyn 1-night trip
Posted 1 day ago
Quality Inn

More cheap stays in Sheffield

Quality Inn

Quality Inn

372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is €81 per night from 6 Nov to 7 Nov
€81
6 Nov - 7 Nov
includes taxes & fees
8.2/10 Very Good! (1,007 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 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 Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG. 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: Features free self parking, an indoor pool and complimentary wireless Internet access. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG and The Red Lion Inn 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 33 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 Three Mile Pond Wildlife Management Area. A couple of additional sights to add to your itinerary are Mount Everett State Reservation and Thom Reed UFO Monument Park. 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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