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Tonight
26 Aug - 27 Aug
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27 Aug - 28 Aug
This weekend
29 Aug - 31 Aug
Next weekend
5 Sept - 7 Sept

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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, (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 €156
includes taxes & fees
10 Sept - 11 Sept
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, (1002)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is €121
includes taxes & fees
4 Sept - 5 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, (1005)
"Wonderful place to stay"
The price is €119
includes taxes & fees
22 Sept - 23 Sept
The Yankee, Trademark Collection by Wyndham
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (696)
"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 €153
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, (708)
"Pleasant stay"
The price is €99
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, (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 €155
includes taxes & fees
4 Sept - 5 Sept
The Cornell Inn, Lenox & The Berkshires
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"Wonderful old inn; chock full of charm."
The price is €230
includes taxes & fees
10 Sept - 11 Sept
The Red Lion Inn
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, (529)
"Great place , love it, will return"
The price is €141
includes taxes & fees
10 Sept - 11 Sept
The Constance by the Lenox Collection
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (593)
"Amazing place to stay. Can’t wait to go again. "
Berkshire Mountain Lodge
the Alander
American cuisine

the Alander

2.5 star property
9.0 out of 10, Wonderful, (155)
"Loved our stay, staff very attentive and helpful!! "
The price is €135
includes taxes & fees
27 Aug - 28 Aug
the Alander
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cots/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (24)
"Brand new hotel. Really nice staff. Great location to Tanglewood and great rates. "
The price is €129
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
The Brooks Motel
Double Room

The Brooks Motel

2.0 star property
7.8 out of 10, Good, (96)
"Basic, clean and good value for the money."
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, (626)
"It was lovely!"
The price is €61
includes taxes & fees
8 Sept - 9 Sept
Econo Lodge Lee - Great Barrington
Chatham Travel Lodge
Exterior

Chatham Travel Lodge

2.5 star property
7.8 out of 10, Good, (197)
"Nice and quiet"
The price is €111
includes taxes & fees
4 Sept - 5 Sept
Chatham Travel Lodge
The Whitlock
Exterior

The Whitlock

2.0 star property
8.6 out of 10, Excellent, (264)
"Wonderful ambience and people!"
The price is €154
includes taxes & fees
3 Sept - 4 Sept
The Whitlock
Little Cat Lodge
Seasonal outdoor pool

Little Cat Lodge

2.0 star property
9.4 out of 10, Exceptional, (58)
"Great place"
Little Cat Lodge
Blackberry River Inn
Library

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 €161
includes taxes & fees
2 Sept - 3 Sept
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, (732)
"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 €129
includes taxes & fees
11 Sept - 12 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Berkshire Travel Lodge
Outdoor pool

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (438)
"Property is close to Tanglewood Musical Venues. Parking is easy. The rooms are impeccably clean and the office manger was curteous."
The price is €65
includes taxes & fees
14 Sept - 15 Sept
Berkshire Travel Lodge
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (401)
"Peaceful area and great staff; Thank you for the service and experience "
The price is €103
includes taxes & fees
2 Sept - 3 Sept
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

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

Top Sheffield Hotel Reviews

Berkshire Travel Lodge

Berkshire Travel Lodge

10/10 Excellent
"The room I had must have been renovated recently, but none the less, very clean The bathroom nerd renovation but again, was clean. The front desk gentleman at check-in was awesome, very friendly and upbeat. This is your basic Roadside Motel, there are eateries and fuel literally right down the road, and very convenient to I-90, right off Route 22. I intend on using this Motel again when up there! "
John 1-night trip
Posted 2 days ago
Berkshire Travel Lodge

More cheap stays in Sheffield

More cheap stays in Sheffield

Quality Inn

Quality Inn

372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is €88 per night from 8 Sept to 9 Sept
€88
8 Sept - 9 Sept
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.