Sheffield Hotels from S$91

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26 Jul - 27 Jul
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Top 10 trending Sheffield hotels

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, (26)
"Always perfect! "
The price is S$312
includes taxes & fees
27 Jul - 28 Jul
Wilder House Berkshires
Becket Motel
Stunning residential building with a flat roof and symmetrical facade, featuring six windows and a central door.

Becket Motel

2.5 star property
6.6 out of 10, (58)
"Comfortable stay "
The price is S$165
includes taxes & fees
27 Jul - 28 Jul
Becket Motel
Manor House Inn
Classic elegance abounds in this traditional space, featuring a grand staircase and ornate grandfather clock.

Manor House Inn

3.0 star property
9.2 out of 10, Wonderful, (135)
"Excellent bed and breakfast, room was clean and comfortable."
The price is S$399
includes taxes & fees
28 Jul - 29 Jul
Manor House Inn
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, (119)
"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$245
includes taxes & fees
28 Jul - 29 Jul
Blackberry River Inn
Gedney Farm
Enjoy a serene dining experience in a picturesque countryside setting at Gedney Farm.

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (124)
"Great property"
Gedney Farm
The Old Inn On The Green
Relax in a serene bedroom with a large bed, window, and comfortable chair.

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (87)
"Beautiful room and property. Perfect weekend getaway!"
The price is S$447
includes taxes & fees
28 Jul - 29 Jul
The Old Inn On The Green
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, (395)
"Nice property! a little dated but overall great for 1 night"
The price is S$154
includes taxes & fees
28 Jul - 29 Jul
Locust Tree Bed and Breakfast LLC
Hitching Post Country Motel
Experience the tranquil atmosphere of the Hitching Post Motel, surrounded by lush greenery and beautifully maintained gardens.

Hitching Post Country Motel

2.5 star property
6.6 out of 10, (56)
"It was all I needed Hosts were very gracious. "
The price is S$191
includes taxes & fees
2 Aug - 3 Aug
Hitching Post Country Motel
Pilgrim Inn
Enjoy meals in the dining area with a round table and comfortable seating.

Pilgrim Inn

2.5 star property
5.8 out of 10, (310)
"Great location but no staff at check-in or checkout!"
The price is S$103
includes taxes & fees
4 Aug - 5 Aug
Pilgrim Inn
Quality Inn
Welcome to our reception area, featuring a comfortable seating space with a fireplace, flat-screen TV, and stunning views of the outside.

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1006)
"The complimentary breakfast was amazing!"
The price is S$171
includes taxes & fees
25 Aug - 26 Aug
Quality Inn
Sunset Inn
Enjoy a refreshing swim in our pool surrounded by a tiled edge.

Sunset Inn

2.0 star property
7.6 out of 10, Good, (393)
"No frills but it was a great stay!"
The price is S$149
includes taxes & fees
18 Aug - 19 Aug
Sunset Inn
Chambery Inn
Chambery Inn features a traditional two-story building with a pitched roof and multiple windows.

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
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, (614)
"It was a clean, well-run, low cost option. "
The price is S$91
includes taxes & fees
10 Aug - 11 Aug
Econo Lodge Lee - Great Barrington
Cornwall Inn and Lodge
Relax by the serene pool surrounded by lush greenery and comfortable seating.

Cornwall Inn and Lodge

3.0 star property
9.2 out of 10, Wonderful, (136)
"Cozy small inn with everything needed. Surrounded by massive green and vintage looking lawn. "
The price is S$292
includes taxes & fees
27 Jul - 28 Jul
Cornwall Inn and Lodge
Devonfield Inn B&B
Stunning two-story house with a central entrance and beautifully manicured lawn.

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
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, (1005)
"Beautiful location!"
The price is S$278
includes taxes & fees
3 Aug - 4 Aug
The Black Swan Lee - Lenox, Ascend Hotel Collection
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, (681)
"Terrific place. Spacious, clean, comfortable."
The price is S$246
includes taxes & fees
30 Jul - 31 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (3)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is S$254
includes taxes & fees
28 Jul - 29 Jul
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Relax on the patio with wicker sofas and armchairs, surrounded by a fire feature and a beautiful garden view.

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is S$294
includes taxes & fees
17 Aug - 18 Aug
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Enjoy a serene outdoor setting with two picnic tables on a well-maintained lawn.

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (614)
"Convenient location for my trip"
The price is S$98
includes taxes & fees
27 Jul - 28 Jul
Wagon Wheel 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!

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Top Sheffield Hotel Reviews

The Whitlock

The Whitlock

10/10 Excellent
"I was in town to attend an inspection on a house we made an offer on in nearby Becket. The Whitlock was perfect for me. It was conveniently located, in town, close to dining, and with easy parking. The inn was historic, charming, and had lots of character. It was exactly what I was looking for. There is now staff available on premises from 7 am to 10 pm. I was able to check in on site. The outer doors were locked at night. I would definitely come back."
Michael 2-night trip
Posted 3 days ago
The Whitlock

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: Offers 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 34 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.