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Aug 25 - Aug 26
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Compare 1,256 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Wilder House Berkshires
Wilder House Berkshires Room 3 | 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 ₩239,082
₩267,055 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, (1002)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is ₩175,230
₩195,731 total
includes taxes & fees
Sep 1 - Sep 2
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 ₩173,086
₩193,342 total
includes taxes & fees
Sep 21 - Sep 22
The Yankee, Trademark Collection by Wyndham
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (695)
"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 ₩222,259
₩248,264 total
includes taxes & fees
Sep 1 - Sep 2
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, (708)
"Pleasant stay"
The price is ₩126,611
₩160,744 total
includes taxes & fees
Sep 2 - Sep 3
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 ₩176,656
₩251,415 total
includes taxes & fees
Sep 1 - Sep 2
The Cornell Inn, Lenox & The Berkshires
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"Wonderful old inn; chock full of charm."
The price is ₩275,332
₩369,360 total
includes taxes & fees
Sep 10 - Sep 11
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, (529)
"Great place , love it, will return"
The price is ₩201,947
₩225,575 total
includes taxes & fees
Sep 17 - Sep 18
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, (593)
"Amazing place to stay. Can’t wait to go again. "
The price is ₩106,197
₩149,532 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, (155)
"Loved our stay, staff very attentive and helpful!! "
The price is ₩221,373
₩247,938 total
includes taxes & fees
Aug 27 - Aug 28
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, (24)
"Brand new hotel. Really nice staff. Great location to Tanglewood and great rates. "
The price is ₩186,991
₩208,870 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
The Brooks Motel
Double Room | 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 ₩150,838
₩168,937 total
includes taxes & fees
Aug 27 - Aug 28
The Brooks Motel
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/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 ₩88,203
₩98,522 total
includes taxes & fees
Sep 9 - Sep 10
Econo Lodge Lee - Great Barrington
Chatham Travel Lodge
Exterior

Chatham Travel Lodge

2.5 star property
7.8 out of 10, Good, (197)
"Nice and quiet"
The price is ₩160,481
₩179,740 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, (264)
"Wonderful ambience and people!"
The price is ₩224,140
₩250,365 total
includes taxes & fees
Sep 3 - Sep 4
The Whitlock
Little Cat Lodge
Seasonal outdoor pool

Little Cat Lodge

2.0 star property
9.4 out of 10, Exceptional, (58)
"Great place"
The price is ₩247,799
₩277,535 total
includes taxes & fees
Aug 27 - Aug 28
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 ₩227,391
₩261,500 total
includes taxes & fees
Sep 2 - Sep 3
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, (732)
"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 ₩197,852
₩221,001 total
includes taxes & fees
Sep 10 - Sep 11
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 ₩93,378
₩104,585 total
includes taxes & fees
Sep 14 - Sep 15
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, (401)
"A positively delightful B&B in a beautiful town. "
The price is ₩145,276
₩167,067 total
includes taxes & fees
Aug 27 - Aug 28
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

The Constance by the Lenox Collection

The Constance by the Lenox Collection

10/10 Excellent
"We enjoyed our stay at the Whitlock (part of the same management as the Constance). Good restaurants easy to walk to. Quiet. Only thing we missed was a comfortable armchair in the bedroom."
James 1-night trip
Posted 12 hours ago
The Constance by the Lenox Collection

More cheap stays in Sheffield

More cheap stays in Sheffield

Quality Inn

Quality Inn

372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is ₩128,189 per night from Sep 8 to Sep 9
₩128,189
₩143,186 total
Sep 8 - Sep 9
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.