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Find Hotels with Bars in Stockbridge, MA

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Check availability on Stockbridge Hotels with Bars

Top Stockbridge Hotels with Bars

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 512
AED 736 total
includes taxes & fees
12 Nov - 13 Nov
The Red Lion Inn
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.6 out of 10, Exceptional, (9)
"Very friendly with dog. No complaints with accommodations "
United States
Lilian
The price is AED 496
AED 554 total
includes taxes & fees
16 Nov - 17 Nov
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, (1002)
"Great place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
The price is AED 372
AED 415 total
includes taxes & fees
18 Nov - 19 Nov
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, (947)
"Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned."
United States
Stacey
The price is AED 360
AED 402 total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn & Suites Pittsfield-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, (656)
"Lovely hotel, room was great along with the staff and the grounds where beautiful. Thank you."
United States
Vicki
The price is AED 408
AED 456 total
includes taxes & fees
16 Nov - 17 Nov
Hilton Garden Inn Lenox Pittsfield
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
9.2 out of 10, Wonderful, (586)
"Fabulous place"
United States
Mary
The price is AED 466
AED 521 total
includes taxes & fees
23 Nov - 24 Nov
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, (781)
"Place was great!"
United States
Benjamin
The price is AED 492
AED 601 total
includes taxes & fees
12 Nov - 13 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (794)
"Easy parking, great community spaces, beautiful decor! "
United States
Kerry
The price is AED 340
AED 380 total
includes taxes & fees
16 Nov - 17 Nov
Berkshires Untold
Front of property - evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (795)
"Clean room and staff was super friendly"
United States
Yuen
The price is AED 490
AED 547 total
includes taxes & fees
20 Nov - 21 Nov
Hotel On North
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
9.4 out of 10, Exceptional, (13)
"Prospect was a wonderful stay with very friendly staff. The property is very well maintained. We had a great time with the all the lake activities. Would definitely recommend for a quick getaway "
United States
Andy
The price is AED 858
AED 1,082 total
includes taxes & fees
11 Nov - 12 Nov
Prospect Berkshires
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We came here because it was off season, great price, and it had an indoor pool. "
Monica 3-night trip
Posted 5 hours ago
Vacation Village in the Berkshires

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Frequently asked questions

Searching for hotels with bars in Stockbridge?
Stockbridge offers 52 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. Tanglewood Suites: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood: Lodge with restaurant. Enjoy the bar, free WiFi, and free parking. Vacation Village in the Berkshires: Enjoy the bar, free breakfast, and free WiFi. Berkshire Mountain Lodge: 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 Housatonic River. 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.