Find Hotels with Bars in Lenox, MA

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Check availability on Lenox Hotels with Bars

Top Lenox Hotels with Bars

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
9.2 out of 10, Wonderful, (1000)
"Loved the Yankee Inn!"
The price is NT$5,022
NT$5,609 total
includes taxes & fees
Aug 25 - Aug 26
The Yankee, Trademark Collection by Wyndham
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, (1000)
"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 NT$3,960
NT$5,585 total
includes taxes & fees
Aug 27 - Aug 28
The Cornell Inn, Lenox & The Berkshires
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, (839)
"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 NT$3,833
NT$4,282 total
includes taxes & fees
Aug 17 - Aug 18
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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, (654)
"It's a clean, nice place. And easy to get to the surrounding towns."
The price is NT$16,811
NT$18,779 total
includes taxes & fees
Aug 8 - Aug 9
Berkshires Untold
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 NT$6,028
NT$6,734 total
includes taxes & fees
Aug 17 - Aug 18
Courtyard by Marriott Lenox Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Play a round of golf amidst lush surroundings and scenic obstacles.

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (682)
"Had a great time"
The price is NT$3,909
NT$4,781 total
includes taxes & fees
Aug 6 - Aug 7
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Hilton Garden Inn Lenox Pittsfield
Relax on the patio with wicker sofas and armchairs, surrounded by a fire feature and a beautiful garden view.

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is NT$6,117
NT$6,833 total
includes taxes & fees
Aug 17 - Aug 18
Hilton Garden Inn Lenox Pittsfield
Brook Farm Inn
Relax in this inviting room with a comfortable bed, fireplace, and thoughtful amenities.

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (155)
"Maureen and her lovely staff operate a first class B&B. Thoughtful amenities and conveniences, clean and comfortable. Amazing home cooked breakfast, both plentiful and delicious. Thank you"
Brook Farm Inn
Hampton Terrace Inn
Welcome to this charming two-story house with a cozy front porch and balcony, featuring a wreath above the door and green shutters.

Hampton Terrace Inn

4.0 star property
9.0 out of 10, Wonderful, (42)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
The price is NT$10,094
NT$11,275 total
includes taxes & fees
Aug 11 - Aug 12
Hampton Terrace Inn
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 Lenox Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Great place. Kids loved it. Friendly staff and guests. "
Anonymous traveler 2-night trip
Posted 21 hours ago
Vacation Village in the Berkshires

Frequently asked questions

Searching for hotels with bars in Lenox?
If you'd like a place to stay where you can enjoy a beer after sightseeing, Lenox features 121 hotels and other lodging options, including 11 accommodations with an onsite bar. While you're here, consider a visit to Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company.
What are the best hotels with bars in Lenox?
Here's some of the top Lenox accommodations with bars: Berkshires Untold: Lodge with restaurant. Enjoy the bar, free WiFi, and free parking. The Yankee, Trademark Collection by Wyndham: Enjoy the bar, free breakfast, and free WiFi. Courtyard by Marriott Lenox Berkshires: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Brook Farm Inn: Enjoy the bar, free breakfast, and free WiFi. The Cornell Inn, Lenox & The Berkshires: B&B with restaurant. Enjoy the bar, free breakfast, and free WiFi.
How many hotels with bars on site can I expect to find in Lenox?
Expedia has 11 hotels with a bar in Lenox.
What is there to do in Lenox?
In the area, you can visit Ventfort Hall Mansion and Gilded Age Museum, Shakespeare and Company, and Tanglewood Music Center, then find a cozy spot for a nightcap. Other places to see include The Mount and Housatonic River. Lenox is appreciated for its museums and live music.
When is the best time to visit Lenox?
Visiting local bars in Lenox is more fun when you know what the weather holds. These temperatures and rainfall averages can help you decide 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 Lenox are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
How can I get to Lenox and around the area?
You might want to make the most of these transportation choices in and around Lenox: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 4.7 mi (7.6 km) away from the city center. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.8 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.