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7 Aug - 8 Aug
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8 Aug - 10 Aug
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Top 10 trending Sheffield hotels

Wilder House Berkshires
Wilder House Berkshires Room 3

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (28)
"Always perfect! "
The price is €189
includes taxes & fees
17 Aug - 18 Aug
Wilder House Berkshires
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Beautiful location!"
The price is €121
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1000)
"Wonderful place to stay"
The price is €137
includes taxes & fees
1 Sept - 2 Sept
The Yankee, Trademark Collection by Wyndham
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (663)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is €154
includes taxes & fees
1 Sept - 2 Sept
Berkshires Untold
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, (687)
"Terrific place. Spacious, clean, comfortable."
The price is €109
includes taxes & fees
2 Sept - 3 Sept
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, (1001)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is €156
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (509)
"Property was excellent "
The price is €145
includes taxes & fees
2 Sept - 3 Sept
The Constance by the Lenox Collection
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"Loved our visit"
The price is €219
includes taxes & fees
27 Aug - 28 Aug
The Red Lion Inn
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (546)
"Excellent stay!"
Berkshire Mountain Lodge
Holiday Inn Express & Suites Pittsfield - Berkshires
Free daily buffet breakfast

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
9.6 out of 10, Exceptional, (11)
"Really enjoyed my stay here, definitely need a car to get around"
The price is €146
includes taxes & fees
14 Aug - 15 Aug
Holiday Inn Express & Suites Pittsfield - Berkshires
the Alander
American cuisine

the Alander

2.5 star property
9.0 out of 10, Wonderful, (152)
"Beautiful area. Quiet, peaceful and nicely appointed room. Dinner at the restaurant was excellent. "
The price is €148
includes taxes & fees
14 Aug - 15 Aug
the Alander
The Brooks Motel
Double Room

The Brooks Motel

2.0 star property
7.6 out of 10, Good, (93)
"Basic, clean and good value for the money."
The price is €138
includes taxes & fees
20 Aug - 21 Aug
The Brooks Motel
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (621)
"It was lovely!"
The price is €61
includes taxes & fees
21 Aug - 22 Aug
Econo Lodge Lee - Great Barrington
The Whitlock
Exterior

The Whitlock

2.0 star property
8.6 out of 10, Excellent, (261)
"Lovely hotel in the heart of Lenox. The rooms and property were very nice. The staff was great. We would definitely stay here again!"
The price is €167
includes taxes & fees
2 Sept - 3 Sept
The Whitlock
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (320)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is €166
includes taxes & fees
3 Sept - 4 Sept
The Dewey
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, (724)
"Was the perfect stop over for our way home. All the employees were extremely friendly. "
The price is €145
includes taxes & fees
25 Aug - 26 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Chatham Travel Lodge
Exterior

Chatham Travel Lodge

2.5 star property
7.6 out of 10, Good, (186)
"Nice and quiet"
The price is €107
includes taxes & fees
11 Aug - 12 Aug
Chatham Travel Lodge
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (123)
"We had a vey clean room with a comfortable bed The breakfast was awesome as was the entire staff. Enjoyed our stay"
The price is €162
includes taxes & fees
2 Sept - 3 Sept
Blackberry River Inn
Prospect Berkshires
1 bedroom, Egyptian cotton sheets, premium bedding, down duvets

Prospect Berkshires

2.0 star property
9.0 out of 10, Wonderful, (2)
"So fantastic!! The cabins are gorgeous and very well appointed. We are going back!"
The price is €436
includes taxes & fees
12 Aug - 13 Aug
Prospect Berkshires
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (398)
"Nice property! a little dated but overall great for 1 night"
The price is €104
includes taxes & fees
10 Aug - 11 Aug
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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Learn more about Sheffield

Love casinos and history? Get away to Sheffield!

See all hotels in Sheffield

Top Sheffield Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Wonderful place to stay"
Adair 1-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

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: Provides 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 35 hotels and other accommodation options to choose from. Find out more about Sheffield.

What are the top places to visit in Sheffield?

The picturesque setting of Housatonic River and Mount Everett State Reservation exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Magnolia Bluffs Casino 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.