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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, (27)
"Always perfect! "
The price is P12,387
P13,836 total
includes taxes & fees
Aug 13 - Aug 14
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 P5,718
P8,303 total
includes taxes & fees
Aug 10 - Aug 11
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 P16,925
P18,786 total
includes taxes & fees
Aug 10 - Aug 11
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, (120)
"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 P9,506
P10,932 total
includes taxes & fees
Aug 12 - Aug 13
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, (125)
"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 P16,631
P20,068 total
includes taxes & fees
Jul 31 - Aug 1
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, (397)
"Nice property! a little dated but overall great for 1 night"
The price is P6,022
P6,925 total
includes taxes & fees
Jul 31 - Aug 1
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, (59)
"For a low budget hotel, it was everything I could ask for Clean room, comfortable bed Wi-Fi very good service It’s not the four seasons, and I didn’t expect it to be"
The price is P7,433
P8,548 total
includes taxes & fees
Aug 9 - Aug 10
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 P4,594
P5,131 total
includes taxes & fees
Jul 31 - Aug 1
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, (1009)
"Best Quality- excellent location for dining - walk to restaurants. "
The price is P7,146
P7,982 total
includes taxes & fees
Aug 26 - Aug 27
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, (396)
"No frills but it was a great stay!"
The price is P6,308
P7,046 total
includes taxes & fees
Aug 18 - Aug 19
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, (615)
"It was a clean, well-run, low cost option. "
The price is P3,656
P4,084 total
includes taxes & fees
Aug 13 - Aug 14
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 P11,412
P13,124 total
includes taxes & fees
Jul 31 - Aug 1
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, (1000)
"Beautiful location!"
The price is P11,163
P12,469 total
includes taxes & fees
Aug 6 - Aug 7
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, (682)
"Had a great time"
The price is P7,544
P9,227 total
includes taxes & fees
Aug 6 - Aug 7
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, (4)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is P9,118
P10,185 total
includes taxes & fees
Jul 31 - Aug 1
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 P11,806
P13,187 total
includes taxes & fees
Aug 24 - Aug 25
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 P3,957
P4,420 total
includes taxes & fees
Jul 31 - Aug 1
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

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Top Sheffield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Loved our visit"
Barbara 1-night trip
Posted 8 hours 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 traveler data. This B&B offers free breakfast and free parking. Other good choices 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 room reservations are refundable provided that you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your check-in date. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.

Where can I learn more about changing or cancelling my trip to Sheffield?

To access more information about changing or cancelling your trip to Sheffield, go to https://www.expedia.com/service/.

What's the best place to stay near Ashley House?

Sheffield 1802 House is one of the top choices for your stay based on our traveler data, and this 3.5-star B&B offers free breakfast and free parking. It's located 3.2 mi (5.1 km) from Ashley House. Another good option is Locust Tree Bed and Breakfast, located 3.8 mi (6.2 km) away.

What about the best place to stay near Magnolia Bluffs Casino?

One of the top choices for your stay is Sheffield 1802 House, located 1.6 mi (2.6 km) from Magnolia Bluffs Casino, and this 3.5-star B&B offers free breakfast and free parking.

What are some accommodations with pools in Sheffield?

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Berkshire Mountain Lodge and The Red Lion Inn are a couple of other choices that offer an onsite pool. View all hotels with pools in Sheffield.

What is the best accommodation for staying close to Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

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 accommodations to choose from. Find out more about Sheffield.

What should I see while I'm 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 agenda are Magnolia Bluffs Casino and Thom Reed UFO Monument Park. Check out what more to see and do in Expedia's Sheffield guide.

What's the weather like in Sheffield?

The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.