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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
9.8 out of 10, Exceptional, (36)
"Highly recommend this beautiful bed & breakfast! The room was wonderful and overlooked the property, the breakfast was delicious, and the hospitality was amazing. I had a fantastic stay, and will definitely stay at The Wilder House again when I'm in the area."
The price is ₩246,444
₩275,279 total
includes taxes & fees
Nov 2 - Nov 3
Wilder House Berkshires
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1006)
"Great Indian restaurant in the hotel!"
The price is ₩151,532
₩169,261 total
includes taxes & fees
Nov 2 - Nov 3
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (753)
"Easy parking, great community spaces, beautiful decor! "
The price is ₩124,789
₩139,390 total
includes taxes & fees
Nov 2 - Nov 3
Berkshires Untold
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1003)
"Great location, very clean!"
The price is ₩191,251
₩213,628 total
includes taxes & fees
Nov 2 - Nov 3
The Yankee, Trademark Collection by Wyndham
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, (751)
"The lodging was convenient to all the area attractions."
The price is ₩165,579
₩204,861 total
includes taxes & fees
Nov 2 - Nov 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, (1005)
"Very friendly staff. "
The price is ₩182,094
₩259,155 total
includes taxes & fees
Oct 28 - Oct 29
The Cornell Inn, Lenox & The Berkshires
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (687)
"Great stay, perfect "
The price is ₩132,924
₩180,338 total
includes taxes & fees
Nov 2 - Nov 3
Berkshire Mountain Lodge
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1007)
"great place have stayed several times, and hope to return."
The price is ₩212,501
₩301,081 total
includes taxes & fees
Nov 6 - Nov 7
The Red Lion Inn
The Brooks Motel
Double Room | Egyptian cotton sheets, premium bedding, memory foam beds, desk

The Brooks Motel

2.0 star property
7.6 out of 10, Good, (104)
"The room was very comfortable & clean. It had a really nice shower, which is very important for us when travelling. Thank you! See you again some time."
The price is ₩168,147
₩188,325 total
includes taxes & fees
Oct 14 - Oct 15
The Brooks Motel
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby sitting area

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.4 out of 10, Exceptional, (52)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is ₩170,001
₩189,882 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
the Alander
Dinner served, American cuisine

the Alander

2.5 star property
9.0 out of 10, Wonderful, (170)
"Good location, clean and nice touches in the rooms (french press coffee pot and freshly ground coffee, Harney teas, Saratoga Spring water, and other nice amenities). The fire pits are a nice plus! "
The price is ₩228,189
₩255,573 total
includes taxes & fees
Oct 13 - Oct 14
the Alander
The Constance by the Lenox Collection
Front of property

The Constance by the Lenox Collection

3.5 star property
8.4 out of 10, Very Good, (550)
"Very quiet and comfortable "
The price is ₩137,179
₩153,229 total
includes taxes & fees
Nov 3 - Nov 4
The Constance by the Lenox Collection
Chatham Travel Lodge
Exterior

Chatham Travel Lodge

2.5 star property
7.8 out of 10, Good, (202)
"Clean, comfortable room. Check in was easy."
The price is ₩165,423
₩185,275 total
includes taxes & fees
Oct 12 - Oct 13
Chatham Travel Lodge
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (142)
"Loved everything especially Lucas and Joe💟☮️"
The price is ₩234,393
₩269,552 total
includes taxes & fees
Oct 14 - Oct 15
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, (743)
"The property is very nice and the staff was extremely friendly and helpful."
The price is ₩203,944
₩227,805 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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, (635)
"Easy check in"
The price is ₩89,407
₩99,868 total
includes taxes & fees
Nov 2 - Nov 3
Econo Lodge Lee - Great Barrington
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (406)
"Peaceful area and great staff; Thank you for the service and experience "
The price is ₩149,749
₩172,211 total
includes taxes & fees
Oct 13 - Oct 14
Locust Tree Bed and Breakfast LLC
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (576)
"The front desk, food service, and housekeeping staff were all very friendly. The room was immaculate as well. "
The price is ₩181,125
₩202,316 total
includes taxes & fees
Nov 9 - Nov 10
Courtyard by Marriott Lenox Berkshires
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (670)
"Very comfortable and safe."
The price is ₩147,182
₩164,396 total
includes taxes & fees
Nov 10 - Nov 11
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Prospect Berkshires
Egyptian cotton sheets, premium bedding, down comforters, minibar

Prospect Berkshires

3.0 star property
9.0 out of 10, Wonderful, (7)
"Gorgeous thoughtfully designed cabins with so many amenities/activities. Cliff house restaurant was delicious. Perfect getaway. "
The price is ₩417,158
₩513,756 total
includes taxes & fees
Nov 2 - Nov 3
Prospect 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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Stay near popular Sheffield attractions

Ashley House

You can learn about the history of Sheffield with a trip to Ashley House. Discover the area's breweries or seek out the hiking trails.
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Bartholomew's Cobble

You can take time to visit Bartholomew's Cobble during your travels to Sheffield. Make some time to visit the casinos while you're in the area.
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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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent
"I would say 4.7 out of five stars. Clean friendly, very comfortable bed nice breakfast. My only complaint would be the toilet paper could be a better quality…"
Kenneth 2-night trip
Posted 22 hours ago
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

More cheap stays in Sheffield

Quality Inn

Quality Inn

372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is ₩120,013 per night from Nov 2 to Nov 3
₩120,013
₩134,055 total
Nov 2 - Nov 3
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)

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 Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG. 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: Features free self parking, an indoor pool, and complimentary wireless internet access. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG 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 33 hotels and other accommodations to choose from. Find out more about Sheffield.
What should I see while I'm in Sheffield?
Favorite places to visit include Housatonic River, Magnolia Bluffs Casino, and Three Mile Pond Wildlife Management Area. A couple of additional sights to add to your agenda are Mount Everett State Reservation 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.

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