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2 Aug - 3 Aug
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Top 10 Sheffield hotels and places to stay

Wilder House Berkshires
Cozy retreat with a large bed, bedside tables, and a chandelier.

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (28)
"Always perfect! "
The price is ฿7,022
฿7,843 total
includes taxes & fees
1 Sept - 2 Sept
Wilder House Berkshires
The Yankee, Trademark Collection by Wyndham
Classic hotel entrance with a covered walkway, surrounded by beautifully maintained gardens.

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Loved the Yankee Inn!"
The price is ฿5,169
฿5,773 total
includes taxes & fees
1 Sept - 2 Sept
The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, Ascend Hotel Collection
Relax in a serene lakeside setting with Adirondack chairs and a tranquil atmosphere.

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Beautiful location!"
The price is ฿4,117
฿4,599 total
includes taxes & fees
1 Sept - 2 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Constance by the Lenox Collection
Situated in a tranquil setting, The Whittock offers a traditional home with a covered front porch and mature trees surrounding the property.

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (507)
"Property was excellent "
The price is ฿5,225
฿5,836 total
includes taxes & fees
2 Sept - 3 Sept
The Constance by the Lenox Collection
The Cornell Inn, Lenox & The Berkshires
Traditional two-story house with a welcoming porch and balcony, set amidst snow-covered trees.

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is ฿4,333
฿6,110 total
includes taxes & fees
27 Aug - 28 Aug
The Cornell Inn, Lenox & The Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Play a round of golf amidst lush surroundings and scenic obstacles.

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

3.5 star property
9.0 out of 10, Wonderful, (683)
"Had a great time"
The price is ฿3,875
฿4,782 total
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Berkshires Untold
Relax in a stylish space with a bar area, seating area, and large windows offering views of the outdoors.

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (656)
"It's a clean, nice place. And easy to get to the surrounding towns."
The price is ฿13,787
฿15,400 total
includes taxes & fees
8 Aug - 9 Aug
Berkshires Untold
The Red Lion Inn
Relax by the serene pool surrounded by lounge chairs and umbrellas.

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1002)
"Loved our visit"
The price is ฿6,144
฿8,315 total
includes taxes & fees
27 Aug - 28 Aug
The Red Lion Inn
the Alander
Enjoy a meal under the shade of a pergola surrounded by lush greenery.

the Alander

2.5 star property
9.0 out of 10, Wonderful, (151)
"Beautiful area. Quiet, peaceful and nicely appointed room. Dinner at the restaurant was excellent. "
The price is ฿5,201
฿5,617 total
includes taxes & fees
4 Aug - 5 Aug
the Alander
Econo Lodge Lee - Great Barrington
Relax in comfort with a large bed, two bedside tables, and a balcony with a view.

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (615)
"It was a clean, well-run, low cost option. "
The price is ฿2,072
฿2,315 total
includes taxes & fees
21 Aug - 22 Aug
Econo Lodge Lee - Great Barrington
The Brooks Motel
Two beds with white bedding, a unique wall paneling, and a cozy reading area.

The Brooks Motel

2.0 star property
7.8 out of 10, Good, (90)
"Basic, clean and good value for the money."
The price is ฿4,291
฿4,806 total
includes taxes & fees
4 Aug - 5 Aug
The Brooks Motel
Berkshire Mountain Lodge
Enjoy cooking in this well-equipped kitchen with a double sink, oven, and gas range.

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (535)
"Excellent stay!"
The price is ฿3,084
฿4,171 total
includes taxes & fees
24 Aug - 25 Aug
Berkshire Mountain Lodge
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Relax in a welcoming space with comfortable seating and a stunning chandelier.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (723)
"Was the perfect stop over for our way home. All the employees were extremely friendly. "
The price is ฿4,909
฿5,483 total
includes taxes & fees
27 Aug - 28 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 ฿6,046
฿6,754 total
includes taxes & fees
2 Sept - 3 Sept
The Whitlock
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (318)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is ฿5,884
฿6,572 total
includes taxes & fees
2 Sept - 3 Sept
The Dewey
Chatham Travel Lodge
Stroll through the serene garden, surrounded by lush greenery and vibrant flowers beneath a charming pergola.

Chatham Travel Lodge

2.5 star property
7.6 out of 10, Good, (184)
"Nice and quiet"
The price is ฿3,770
฿4,072 total
includes taxes & fees
3 Aug - 4 Aug
Chatham Travel Lodge
Courtyard by Marriott Lenox Berkshires
Relax by the fire pit in our outdoor seating area, surrounded by wicker furniture under a covered patio with a flat roof.

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (566)
"After coming to Lenox for 15 years, I can easily say this is the best in town. "
The price is ฿4,941
฿5,519 total
includes taxes & fees
1 Sept - 2 Sept
Courtyard by Marriott Lenox Berkshires
Locust Tree Bed and Breakfast LLC
Relax on the covered porch with two comfortable rocking chairs and lush green surroundings.

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (397)
"Nice property! a little dated but overall great for 1 night"
The price is ฿3,413
฿3,925 total
includes taxes & fees
3 Aug - 4 Aug
Locust Tree Bed and Breakfast LLC
Holiday Inn Express & Suites Pittsfield - Berkshires
Enjoy a diverse selection of hot and cold dishes at our buffet.

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (4)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is ฿5,222
฿5,833 total
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires
Blackberry River Inn
Cozy living room with a traditional fireplace, armchairs, and a sofa, perfect for relaxing.

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (122)
"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 ฿5,343
฿6,144 total
includes taxes & fees
2 Sept - 3 Sept
Blackberry River Inn
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 Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Loved our visit"
Barbara 1-night trip
Posted 3 days ago
The Red Lion Inn

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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Provides 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. Berkshire Mountain Lodge 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.