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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

Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1005)
"Old time charm and hot tub under the stars"
United States
Lori
The price is AED 496
AED 718 total
includes taxes & fees
14 Jan - 15 Jan
The Red Lion Inn
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"The room we stayed in was extremely clean and comfy. The whole hotel was very nice and had an awesome breakfast. Will be staying here again for sure. "
United States
Keith
The price is AED 511
AED 570 total
includes taxes & fees
19 Jan - 20 Jan
Element Lenox Berkshires
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (1007)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
The price is AED 360
AED 402 total
includes taxes & fees
9 Jan - 10 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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, (1010)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is AED 372
AED 415 total
includes taxes & fees
19 Jan - 20 Jan
The Yankee, Trademark Collection by Wyndham
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, (660)
" Nice staff - beautiful hotel!"
United States
MARY
The price is AED 470
AED 525 total
includes taxes & fees
9 Jan - 10 Jan
Hilton Garden Inn Lenox Pittsfield
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, (817)
"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
15 Jan - 16 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Interior
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (832)
"Great hospitality and beautiful design. Our family had a great time!"
United States
Alison
The price is AED 403
AED 450 total
includes taxes & fees
11 Jan - 12 Jan
Berkshires Untold
View from property
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18)
"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 926
AED 1,157 total
includes taxes & fees
26 Jan - 27 Jan
Prospect Berkshires
Exterior
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, (594)
"new property, modern and centrally located in the Berkshires. Located very close to Lenox, giving you many dining options "
United States
Francisco
The price is AED 529
AED 591 total
includes taxes & fees
8 Jan - 9 Jan
Courtyard by Marriott Lenox Berkshires
Front of property - evening/night
Hotel On North

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (811)
"Great staff, room was huge and comfortable. "
United States
Cameron
The price is AED 547
AED 611 total
includes taxes & fees
8 Jan - 9 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.
View all properties

Top Stockbridge Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Great staff, room was huge and comfortable. "
Cameron 1-night trip
Posted 2 days ago
Hotel On North

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Frequently asked questions

Searching for hotels with bars in Stockbridge?
Stockbridge offers 45 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: Enjoy the bar, free breakfast, and free WiFi. Vacation Village in the Berkshires: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. The Yankee, Trademark Collection by Wyndham: Lodge with restaurant. Enjoy the bar, free WiFi, and free parking. Holiday Inn & Suites Pittsfield-Berkshires by IHG: 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.