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Top 10 trending Sheffield hotels

Wilder House Berkshires
1 bedroom, premium bedding, individually decorated

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (26)
"Always perfect! "
The price is P12,885
P14,393 total
includes taxes & fees
Jul 21 - Jul 22
Wilder House Berkshires
Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (58)
"Comfortable stay "
The price is P5,440
P7,996 total
includes taxes & fees
Jul 27 - Jul 28
Becket Motel
Manor House Inn
Interior detail

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 P16,951
P18,816 total
includes taxes & fees
Jul 22 - Jul 23
Manor House Inn
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (117)
"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 P9,521
P10,949 total
includes taxes & fees
Jul 21 - Jul 22
Blackberry River Inn
Gedney Farm
Front of property

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (122)
"Beautiful, clean property that is well run."
Gedney Farm
The Old Inn On The Green
Premium bedding, individually decorated, individually furnished

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 P16,608
P20,040 total
includes taxes & fees
Jul 20 - Jul 21
The Old Inn On The Green
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (392)
"A positively delightful B&B in a beautiful town. "
The price is P6,005
P6,906 total
includes taxes & fees
Aug 2 - Aug 3
Locust Tree Bed and Breakfast LLC
Hitching Post Country Motel
Front of property

Hitching Post Country Motel

2.5 star property
6.4 out of 10, (53)
"It was all I needed Hosts were very gracious. "
The price is P7,435
P8,550 total
includes taxes & fees
Aug 19 - Aug 20
Hitching Post Country Motel
Pilgrim Inn
Lobby

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 P5,097
P5,693 total
includes taxes & fees
Jul 31 - Aug 1
Pilgrim Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1000)
"Friendly staff, easy parking"
The price is P7,740
P8,645 total
includes taxes & fees
Aug 4 - Aug 5
Quality Inn
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (391)
"No frills but it was a great stay!"
The price is P6,299
P7,037 total
includes taxes & fees
Aug 18 - Aug 19
Sunset Inn
Chambery Inn
Front of property

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

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (611)
"It is clean and reasonably priced. We were comfortable and close to Tanglewood. "
The price is P3,651
P4,078 total
includes taxes & fees
Aug 3 - Aug 4
Econo Lodge Lee - Great Barrington
Cornwall Inn and Lodge
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

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 P11,396
P13,106 total
includes taxes & fees
Jul 20 - Jul 21
Cornwall Inn and Lodge
Devonfield Inn B&B
Front of property - evening/night

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
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Beautiful location!"
The price is P11,147
P12,451 total
includes taxes & fees
Jul 31 - Aug 1
The Black Swan Lee - Lenox, Ascend Hotel Collection
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, (676)
"Had a great time"
The price is P7,988
P9,722 total
includes taxes & fees
Jul 22 - Jul 23
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires
Free daily buffet breakfast

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 P10,660
P11,908 total
includes taxes & fees
Jul 21 - Jul 22
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

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 P11,251
P12,567 total
includes taxes & fees
Jul 24 - Jul 25
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (611)
"Convenient location for my trip"
The price is P3,951
P4,414 total
includes taxes & fees
Jul 20 - Jul 21
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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Top Sheffield Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Terrific place. Spacious, clean, comfortable."
Carolyn 2-night trip
Posted 19 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. The Yankee, Trademark Collection by Wyndham 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 34 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.