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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, (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 P9,849
P11,001 total
includes taxes & fees
Sep 9 - Sep 10
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, (1000)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is P7,219
P8,063 total
includes taxes & fees
Sep 2 - Sep 3
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, (1010)
"Wonderful place to stay"
The price is P7,643
P8,537 total
includes taxes & fees
Sep 18 - Sep 19
The Yankee, Trademark Collection by Wyndham
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (687)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is P9,112
P10,178 total
includes taxes & fees
Aug 27 - Aug 28
Berkshires Untold
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, (1000)
"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 P7,277
P10,357 total
includes taxes & fees
Sep 2 - Sep 3
The Cornell Inn, Lenox & The Berkshires
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, (697)
"Pleasant stay"
The price is P5,216
P6,622 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1008)
"Loved our visit"
The price is P10,795
P14,609 total
includes taxes & fees
Aug 26 - Aug 27
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, (523)
"Great place , love it, will return"
The price is P8,524
P9,521 total
includes taxes & fees
Sep 15 - Sep 16
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, (581)
"Amazing place to stay. Can’t wait to go again. "
The price is P3,758
P5,473 total
includes taxes & fees
Sep 7 - Sep 8
Berkshire Mountain Lodge
the Alander
Dinner served, American cuisine

the Alander

2.5 star property
9.0 out of 10, Wonderful, (156)
"Beautiful area. Quiet, peaceful and nicely appointed room. Dinner at the restaurant was excellent. "
The price is P9,119
P10,214 total
includes taxes & fees
Sep 2 - Sep 3
the Alander
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (19)
"Really enjoyed my stay here, definitely need a car to get around"
The price is P7,703
P8,604 total
includes taxes & fees
Sep 2 - Sep 3
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 price is P8,492
P9,512 total
includes taxes & fees
Sep 2 - Sep 3
The Brooks Motel
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, (625)
"It was lovely!"
The price is P3,634
P4,059 total
includes taxes & fees
Sep 2 - Sep 3
Econo Lodge Lee - Great Barrington
Chatham Travel Lodge
Exterior

Chatham Travel Lodge

2.5 star property
7.8 out of 10, Good, (193)
"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 P6,611
P7,404 total
includes taxes & fees
Sep 2 - Sep 3
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 P9,824
P10,973 total
includes taxes & fees
Sep 15 - Sep 16
The Whitlock
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (126)
"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 P9,387
P10,795 total
includes taxes & fees
Sep 2 - Sep 3
Blackberry River Inn
Berkshire Travel Lodge
Outdoor pool

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (435)
"Property is close to Tanglewood Musical Venues. Parking is easy. The rooms are impeccably clean and the office manger was curteous."
The price is P3,847
P4,308 total
includes taxes & fees
Aug 27 - Aug 28
Berkshire Travel Lodge
Little Cat Lodge
Seasonal outdoor pool

Little Cat Lodge

2.0 star property
9.4 out of 10, Exceptional, (57)
"Great place"
Little Cat 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 P5,985
P6,882 total
includes taxes & fees
Aug 22 - Aug 23
Locust Tree Bed and Breakfast LLC
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, (729)
"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 P8,167
P9,123 total
includes taxes & fees
Sep 7 - Sep 8
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

10/10 Excellent
"None "
Maurice 2-night trip
Posted 3 days ago
The Black Swan Lee - Lenox, Ascend Hotel Collection

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 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 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?

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 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 Three Mile Pond Wildlife Management Area. 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.