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Check availability on Lenox Hotels with a Bar

Top Lenox Hotels with a Bar

Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great stay!"
United States
Ann
The price is 2.353.612 ₫
2.629.189 ₫ total
includes taxes & fees
11 Dec - 12 Dec
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, (979)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is 2.444.592 ₫
2.730.609 ₫ total
includes taxes & fees
8 Dec - 9 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is 3.454.601 ₫
3.858.789 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Element Lenox Berkshires
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
The price is 2.721.487 ₫
3.039.902 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Lenox Pittsfield
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (806)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is 2.891.501 ₫
3.229.806 ₫ total
includes taxes & fees
8 Dec - 9 Dec
Berkshires Untold
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, (795)
"Place was great!"
United States
Benjamin
The price is 2.808.512 ₫
3.652.661 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
9.2 out of 10, Wonderful, (588)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is 3.560.085 ₫
3.976.615 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Courtyard by Marriott Lenox Berkshires
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1000)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is 4.406.446 ₫
5.069.660 ₫ total
includes taxes & fees
11 Dec - 12 Dec
The Cornell Inn, Lenox & The Berkshires
Exterior
Hampton Terrace Inn

Hampton Terrace Inn

4.0 star property
Lenox
9.0 out of 10, Wonderful, (43)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is 6.932.936 ₫
7.744.108 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Hampton Terrace Inn
Room (King Room) | Iron/ironing board, free WiFi, bed sheets
Gateways Inn & Restaurant

Gateways Inn & Restaurant

3.0 star property
Lenox
8.0 out of 10, Very good, (192)
"Very well kept property, nice restaurant and is in a great area"
United States
Josephine
The price is 4.408.176 ₫
5.144.341 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Gateways Inn & Restaurant
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 Lenox Hotel Reviews

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Frequently asked questions

Searching for hotels with bars in Lenox?
If you want a place to stay where you can unwind with a late-night cocktail, Lenox features 118 hotels and other properties, including 12 accommodation options with an on-site bar. While you're here, consider a visit to Lenox Library and Ventfort Hall Mansion and Gilded Age Museum.
How many hotels with bars can I expect to find in Lenox?
Expedia has 12 hotels with a bar in Lenox.
What is there to do in Lenox?
In the area, you can visit Lenox Library, Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company, then find a cosy spot for a nightcap. Other places to see include Tanglewood Music Center and Wyndhurst Golf & Club. 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 determine the best time for bar-hopping. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Lenox are January, March, February and November, with each month seeing an average of 18 cm 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 centre. 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, you may want to rent a car for your trip.