Find Hotels with Bars in Sheffield, MA

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Check availability on Sheffield Hotels with Bars

Our top choices for Sheffield hotels with a bar

Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1002)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is SAR 281
SAR 314 total
includes taxes & fees
24 Dec - 25 Dec
The Yankee, Trademark Collection by Wyndham
Lobby
Element Lenox Berkshires

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 SAR 492
SAR 549 total
includes taxes & fees
22 Dec - 23 Dec
Element Lenox Berkshires
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

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 SAR 387
SAR 433 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Lenox Pittsfield
Exterior
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is SAR 946
SAR 1,182 total
includes taxes & fees
17 Dec - 18 Dec
Prospect Berkshires
Exterior
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. "
United States
Joyce
The price is SAR 527
SAR 756 total
includes taxes & fees
6 Jan - 7 January 2026
The Red Lion Inn
Lobby lounge
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (816)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is SAR 411
SAR 460 total
includes taxes & fees
15 Dec - 16 Dec
Berkshires Untold
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

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, (804)
"Place was great!"
United States
Benjamin
The price is SAR 453
SAR 579 total
includes taxes & fees
17 Dec - 18 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (590)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is SAR 507
SAR 566 total
includes taxes & fees
15 Dec - 16 Dec
Courtyard by Marriott Lenox Berkshires
Exterior
the Alander

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (188)
"The Alander has such a fun story, and was a great stay. We were just passing through for the night and it had everything we could need! It reminded me of Rosebud Motel group from Schitts Creek ;) if you know you know! Will definitely be staying again!"
United States
Jenna
The price is SAR 525
SAR 588 total
includes taxes & fees
15 Dec - 16 Dec
the Alander
Porch
Interlaken Inn & Resort

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (270)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is SAR 773
SAR 889 total
includes taxes & fees
17 Dec - 18 Dec
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

Top Sheffield Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The room was fantastic, cozy as can be! Also, as soon as you walk into the lobby it looked wonderful! The Manager, Jennifer was so nice to talk too! She made sure everything with room, etc. was good! She was a delight!"
Mary 1-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

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Frequently asked questions

Searching for hotels with bars in Sheffield?
Sheffield features 34 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: Enjoy the bar, free breakfast, and free WiFi. Antique Farmhouse Totally Restored: 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. The Yankee, Trademark Collection by Wyndham: Enjoy the poolside bar, 2 outdoor pools, and WiFi. Berkshires Untold: 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, Lake Buel, and Mahaiwe Performing Arts Center, 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.