Find Hotels with Bars in Sheffield, MA

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Sheffield Hotels with Bars

Top Sheffield Hotels with Bars

Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1007)
"Great stay!"
United States
Ann
The price is AED 236
AED 264 total
includes taxes & fees
7 Dec - 8 Dec
The Yankee, Trademark Collection by Wyndham
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is AED 481
AED 537 total
includes taxes & fees
11 Dec - 12 Dec
Element Lenox Berkshires
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds
Brook Farm Inn

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (162)
"Comfortable, quiet, convenient location, very friendly staff. "
United States
Susan
Brook Farm Inn
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (800)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is AED 340
AED 380 total
includes taxes & fees
24 Nov - 25 Nov
Berkshires Untold
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
9.2 out of 10, Wonderful, (587)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is AED 466
AED 521 total
includes taxes & fees
30 Nov - 1 Dec
Courtyard by Marriott Lenox Berkshires
Property amenity
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

3.5 star property
South Lee
9.0 out of 10, Wonderful, (789)
"Place was great!"
United States
Benjamin
The price is AED 391
AED 488 total
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
The price is AED 408
AED 456 total
includes taxes & fees
7 Dec - 8 Dec
Hilton Garden Inn Lenox Pittsfield
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is AED 493
AED 714 total
includes taxes & fees
15 Dec - 16 Dec
The Red Lion Inn
Dinner served, American cuisine
the Alander

the Alander

2.5 star property
Copake
9.0 out of 10, Wonderful, (182)
"Very nice clean place in a beautiful area. "
United States
Wayne
The price is AED 441
AED 494 total
includes taxes & fees
24 Nov - 25 Nov
the Alander
Porch
Interlaken Inn & Resort

Interlaken Inn & Resort

3.5 star property
Lakeville
8.2 out of 10, Very Good, (270)
"The staff is courteous and accommodating especially the restaurant staff."
United States
Christian
The price is AED 677
AED 779 total
includes taxes & fees
25 Nov - 26 Nov
Interlaken Inn & Resort
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now

Top Sheffield Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Clean, comfortable facilty"
Julie 1-night trip
Posted 6 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Explore a world of travel with Expedia

Frequently asked questions

Searching for hotels with bars in Sheffield?
Sheffield features 33 hotels and other lodging options to choose from, and likely many will have a bar where you can unwind with a late-night cocktail. While you're here, you can check out Housatonic River and Magnolia Bluffs Casino.
What are the best hotels with bars in Sheffield?
Here are some favorite hotels with bars in and around Sheffield: Wilder House Berkshires: Lodge with restaurant. Enjoy the bar, free WiFi, and free parking. Berkshire Mountain Lodge: Hotel with 3 restaurants. Enjoy the bar, free WiFi, and breakfast. Berkshires Untold: Enjoy the poolside bar, 2 outdoor pools, and WiFi. The Red Lion Inn: Enjoy the bar, free breakfast, and free WiFi. The Black Swan Lee - Lenox, an Ascend Collection Hotel: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking.
What is there to do in Sheffield?
If you have time to explore, consider visiting Ski Butternut, Mahaiwe Performing Arts Center, and Housatonic River Walk, and then find a cozy spot for a nightcap. Other places to see include Housatonic River and Magnolia Bluffs Casino.
When is the best time to visit Sheffield?
Visiting local bars in Sheffield is more fun when you know what the weather holds. These rainfall averages and temperatures can help you determine the best time for bar hopping. 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.
How can I get to Sheffield and around the area?
Here are some of your transportation choices in and around Sheffield: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 22 mi (35.4 km) from the heart of the city. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.9 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.