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Top hotels and accommodation in Sheffield

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (400)
"A positively delightful B&B in a beautiful town. "
The price is NZ$206
includes taxes & fees
24 Aug - 25 Aug
Locust Tree Bed and Breakfast LLC

the Alander

2.5 star property
9.0 out of 10, Wonderful, (155)
"Loved our stay, staff very attentive and helpful!! "
The price is NZ$305
includes taxes & fees
17 Sept - 18 Sept
the Alander

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1002)
"Great location and close enough to walk to shops and restaurants. "
The price is NZ$176
includes taxes & fees
7 Sept - 8 Sept
Quality Inn

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (29)
"Brads and Lara both served a fabulous breakfast. So friendly and welcoming! The bed was very comfortable. Only complaint was that the cabinet, closet door needs to be greased with WD 40 please on the hinges! A terrible & loud screeching noise!"
The price is NZ$325
includes taxes & fees
9 Sept - 10 Sept
Wilder House Berkshires

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is NZ$241
includes taxes & fees
4 Sept - 5 Sept
The Black Swan Lee - Lenox, Ascend Hotel Collection

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (585)
"Amazing place to stay. Can’t wait to go again. "
Berkshire Mountain Lodge

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.4 out of 10, Good, (544)
"Excellent location, friendly service, clean, comfortable room."
The price is NZ$143
includes taxes & fees
4 Sept - 5 Sept
Travelodge by Wyndham Great Barrington Berkshires

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is NZ$289
includes taxes & fees
4 Sept - 5 Sept
Element Lenox Berkshires

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (127)
"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 NZ$322
includes taxes & fees
16 Sept - 17 Sept
Blackberry River Inn

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (692)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise "
The price is NZ$306
includes taxes & fees
4 Sept - 5 Sept
Berkshires Untold

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (20)
"Really enjoyed my stay here, definitely need a car to get around"
The price is NZ$257
includes taxes & fees
14 Sept - 15 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is NZ$310
includes taxes & fees
4 Sept - 5 Sept
The Cornell Inn, Lenox & The Berkshires

Apple Tree Inn

3.0 star property
8.4 out of 10, Very good, (290)
"I loved the pool and the wonderful view from the pool. I felt very safe here and there was an overall sense of being welcomed."
The price is NZ$209
includes taxes & fees
22 Sept - 23 Sept
Apple Tree Inn

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (29)
"Quit eat and comfortable "
The price is NZ$244
includes taxes & fees
15 Sept - 16 Sept
East Rock Inn

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Great staff! Comfortable bed! "
The price is NZ$274
includes taxes & fees
4 Sept - 5 Sept
Hampton Inn & Suites Berkshires-Lenox

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (740)
"A great mom & pop motel. Clean and friendly "
Monument Mountain Motel

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (730)
"We had a nice stay at the Fairfield Inn in Great Barrington. It’s conveniently located not far from downtown and just a short drive to Stockbridge. The front desk staff was welcoming, the room spacious and clean, and plenty of breakfast items to choose from. Definitely recommend!"
The price is NZ$259
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

The Dewey

3.5 star property
8.8 out of 10, Excellent, (321)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is NZ$329
includes taxes & fees
17 Sept - 18 Sept
The Dewey

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1003)
"Wonderful place to stay"
The price is NZ$238
includes taxes & fees
21 Sept - 22 Sept
The Yankee, Trademark Collection by Wyndham

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (786)
"My stay was perfect. I can't wait to stay there again. "
The price is NZ$150
includes taxes & fees
4 Sept - 5 Sept
Howard Johnson by Wyndham Lenox
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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Check out pet-friendly hotels in Sheffield

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.

Stay near top Sheffield attractions

Magnolia Bluffs Casino

Magnolia Bluffs Casino

Why not roll the dice with a visit to Magnolia Bluffs Casino during your time in Sheffield? Discover the area's breweries or seek out the hiking trails.

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.

Top Sheffield Hotel 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 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. Howard Johnson by Wyndham Lenox and Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 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 Three Mile Pond Wildlife Management Area. 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.