Find Hotels with Bars in Stockbridge, MA

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Check availability on Stockbridge Hotels with Bars

Our top choices for Stockbridge hotels with a bar

Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,001 reviews)
"Old time charm and hot tub under the stars"
United States
Lori
The price is AED 546
AED 773 total
includes taxes & fees
20 Jan - 21 Jan
The Red Lion Inn
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (16 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is AED 511
AED 570 total
includes taxes & fees
21 Jan - 22 Jan
Element Lenox Berkshires
Exterior

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Everything was great! "
Canada
Daphne
The price is AED 340
AED 380 total
includes taxes & fees
22 Jan - 23 Jan
The Yankee, Trademark Collection by Wyndham
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,000 reviews)
"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"
United States
Melissa
The price is AED 360
AED 402 total
includes taxes & fees
23 Jan - 24 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18 reviews)
"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 AED 740
AED 949 total
includes taxes & fees
25 Jan - 26 Jan
Prospect 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, (818 reviews)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is AED 413
AED 533 total
includes taxes & fees
19 Jan - 20 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (835 reviews)
"Great hospitality and beautiful design. Our family had a great time!"
United States
Alison
The price is AED 324
AED 362 total
includes taxes & fees
20 Jan - 21 Jan
Berkshires Untold
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (661 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is AED 470
AED 525 total
includes taxes & fees
23 Jan - 24 Jan
Hilton Garden Inn Lenox Pittsfield
Exterior

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (196 reviews)
"Nice room and reasonable prices! Will recommend."
United States
Jianyang
The price is AED 514
AED 576 total
includes taxes & fees
19 Jan - 20 Jan
the Alander
Property entrance

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (816 reviews)
"Great staff, room was huge and comfortable. "
United States
Cameron
The price is AED 547
AED 611 total
includes taxes & fees
21 Jan - 22 Jan
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.
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Top Stockbridge Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Clean, very nice bed and linens, pool, jacuzzi, in room fireplace. Balcony right outside of living room. The breakfast was ok, they offered a lot but not top quality. The waffles were very good and the bacon. Overall excellent stay. Conveniently located to everything."
James 2-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 Stockbridge?
Stockbridge offers 46 hotels and other accommodations to choose from, and likely many will have a bar where you can enjoy an evening cocktail after sightseeing. While you're here, you can check out Naumkeag Museum and National Shrine of the Divine Mercy.
What are the best hotels with bars in Stockbridge?
Here are some favorite hotels with bars in and around Stockbridge: The Red Lion Inn: Hotel with 3 restaurants. Enjoy the bar, free WiFi, and breakfast. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Vacation Village in the Berkshires: Enjoy the bar, free breakfast, and free WiFi. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Lodge with restaurant. Enjoy the bar, free WiFi, and free parking. The Yankee, Trademark Collection by Wyndham: Enjoy the poolside bar, 2 outdoor pools, and WiFi.
What is there to do in Stockbridge?
Consider a visit to Naumkeag Museum, National Shrine of the Divine Mercy, and Norman Rockwell Museum, and then find a cozy spot for a nightcap. Other places to see include Berkshire Botanical Garden and Stockbridge Bowl. Stockbridge is appreciated for its bars.
When is the best time to visit Stockbridge?
Visiting local bars in Stockbridge is more fun in good weather. 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 27°F. The snowiest months in Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
How can I get to Stockbridge and around the area?
Here are some of your transportation options in and around Stockbridge: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 9.6 mi (15.5 km) from the heart of the city. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 20 mi (32.3 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.