Hotels with Bars / Lounges in The Berkshires, Massachusetts

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Hotels with Bars / Lounges

Top The Berkshires Hotels with Bars / Lounges

Berkshires Untold
Relax in a stylish space with a bar area, seating area, and large windows offering views of the outdoors.

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (658)
"It's a clean, nice place. And easy to get to the surrounding towns."
The price is P24,669
P27,556 total
includes taxes & fees
Aug 8 - Aug 9
Berkshires Untold
The Red Lion Inn
Relax by the serene pool surrounded by lounge chairs and umbrellas.

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1002)
"Loved our visit"
The price is P10,993
P14,878 total
includes taxes & fees
Aug 6 - Aug 7
The Red Lion Inn
Courtyard by Marriott Lenox Berkshires
Relax by the fire pit in our outdoor seating area, surrounded by wicker furniture under a covered patio with a flat roof.

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (566)
"After coming to Lenox for 15 years, I can easily say this is the best in town. "
The price is P8,841
P9,875 total
includes taxes & fees
Sep 1 - Sep 2
Courtyard by Marriott Lenox Berkshires
The Cornell Inn, Lenox & The Berkshires
Traditional two-story house with a welcoming porch and balcony, set amidst snow-covered trees.

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is P7,752
P10,933 total
includes taxes & fees
Aug 27 - Aug 28
The Cornell Inn, Lenox & The Berkshires
The Yankee, Trademark Collection by Wyndham
Classic hotel entrance with a covered walkway, surrounded by beautifully maintained gardens.

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1001)
"Loved the Yankee Inn!"
The price is P8,850
P9,885 total
includes taxes & fees
Aug 17 - Aug 18
The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Dine in style with a long table set for a memorable meal, surrounded by cushioned chairs and large windows offering a view of the outdoors.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (846)
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "
The price is P6,689
P7,471 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Porches Inn at Mass MoCA
Traditional buildings with welcoming front porches and easy street access.

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (404)
"Very comfortable room that worked great for our family. "
The price is P10,827
P13,393 total
includes taxes & fees
Sep 2 - Sep 3
The Porches Inn at Mass MoCA
Mount Snow Grand Summit Resort
Relax in two comfortable rocking chairs by a crackling fire pit surrounded by a serene landscape.

Mount Snow Grand Summit Resort

3.0 star property
8.6 out of 10, Excellent, (210)
"Very nice being right on the mountain. "
The price is P8,233
P9,854 total
includes taxes & fees
Sep 2 - Sep 3
Mount Snow Grand Summit Resort
Hotel On North
Enjoy a diverse menu at this restaurant, featuring a selection of drinks and a modern design.

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (750)
"Staff were excellent and welcoming."
The price is P10,993
P12,279 total
includes taxes & fees
Aug 5 - Aug 6
Hotel On North
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.

Top The Berkshires Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Food was great!"
Emily 1-night trip
Posted 3 days ago
The Red Lion Inn