Sheffield Hotels from S$97

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24 Aug - 25 Aug
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Top 10 trending Sheffield hotels

Our top choices for Sheffield hotels

Wilder House Berkshires
1 bedroom, premium bedding, individually decorated

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 S$237
includes taxes & fees
9 Sept - 10 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 S$181
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, (1005)
"Wonderful place to stay"
The price is S$179
includes taxes & fees
21 Sept - 22 Sept
The Yankee, Trademark Collection by Wyndham
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (693)
"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 S$230
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, (705)
"Pleasant stay"
The price is S$149
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 S$233
includes taxes & fees
1 Sept - 2 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)
"Loved our visit"
The price is S$322
includes taxes & fees
26 Aug - 27 Aug
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, (527)
"Great place , love it, will return"
The price is S$212
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, (592)
"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 S$230
includes taxes & fees
26 Aug - 27 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, (22)
"Really enjoyed my stay here, definitely need a car to get around"
The price is S$193
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
The Brooks Motel
1 bedroom, Egyptian cotton sheets, premium bedding, memory-foam beds

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
Desk, iron/ironing board, free cots/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (626)
"It was lovely!"
The price is S$91
includes taxes & fees
7 Sept - 8 Sept
Econo Lodge Lee - Great Barrington
Chatham Travel Lodge
Exterior

Chatham Travel Lodge

2.5 star property
7.8 out of 10, Good, (196)
"Chatham Travel lodge was well situated for our trip further north. The area is beautiful. The town of Chatham is close by with restaurants and shopping. The guests in the room above us were noisy for a while, but not after 10 pm. The lodge is old, but the room was clean and perfect for a one night stopover."
The price is S$166
includes taxes & fees
26 Aug - 27 Aug
Chatham Travel Lodge
The Whitlock
Exterior

The Whitlock

2.0 star property
8.6 out of 10, Excellent, (263)
"Wonderful ambience and people!"
The price is S$236
includes taxes & fees
1 Sept - 2 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 S$242
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, (731)
"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 S$205
includes taxes & fees
10 Sept - 11 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 S$97
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, (400)
"A positively delightful B&B in a beautiful town. "
The price is S$155
includes taxes & fees
25 Aug - 26 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

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 Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"I stayed here for a work trip to a remote project site. This place was very impressive for the money. The rooms were large and had everything. The place was clean and staff very pleasant and accommodating. I didn’t expect a lot for what I paid but was pleasantly surprised."
James 5-night trip
Posted 1 day ago
Berkshire Mountain Lodge

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.

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.