Find Hotels with Bars in South Lee, MA

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Check availability on South Lee Hotels with Bars

Our top choices for South Lee hotels with a bar

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, (813)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is NT$3,785
NT$4,841 total
includes taxes & fees
Jan 14 - 2026/1/15
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
The price is NT$4,236
NT$4,732 total
includes taxes & fees
Jan 6 - 2026/1/7
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, (1000)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
The price is NT$2,768
NT$3,092 total
includes taxes & fees
Jan 3 - 2026/1/4
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, (1004)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is NT$3,177
NT$3,548 total
includes taxes & fees
Jan 7 - 2026/1/8
The Yankee, Trademark Collection by Wyndham
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, (1003)
"Old time charm and hot tub under the stars"
United States
Lori
The price is NT$4,707
NT$6,660 total
includes taxes & fees
Jan 14 - 2026/1/15
The Red Lion Inn
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, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is NT$4,013
NT$4,483 total
includes taxes & fees
Jan 2 - 2026/1/3
Hilton Garden Inn Lenox Pittsfield
Egyptian cotton sheets, premium bedding, down comforters, minibar
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 NT$7,908
NT$9,885 total
includes taxes & fees
Jan 14 - 2026/1/15
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)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is NT$4,362
NT$4,872 total
includes taxes & fees
Jan 6 - 2026/1/7
Courtyard by Marriott Lenox Berkshires
Interior
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (823)
"Great hospitality and beautiful design. Our family had a great time!"
United States
Alison
The price is NT$3,974
NT$4,439 total
includes taxes & fees
Jan 6 - 2026/1/7
Berkshires Untold
Dinner served, American cuisine
the Alander

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (193)
"The Alander was a great find! Clean, cozy and super comfortable beds. We loved the complimentary local tea, yogurt and granola. I especially appreciated the maps with local places to explore and the host’s suggestions for activities. I hope I will be able to return in the summer to enjoy the outdoor spaces and the fire pit. Thank you for a great stay!"
United States
Devorah
The price is NT$4,393
NT$4,921 total
includes taxes & fees
Jan 5 - 2026/1/6
the Alander
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 South Lee Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Spotless room, helpful and friendly staff, five-star Indian food at in-house Mint restaurant:-)"
Anne 1-night trip
Posted 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Frequently asked questions

Searching for hotels with bars in South Lee?
South Lee offers 29 properties to choose from, and likely many will have a bar where you can unwind with a late-night cocktail. While you're here, you can check out Housatonic River and Chesterwood.
What are the best hotels with bars in South Lee?
Here are a few of the top hotels with bars in and around South Lee: Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Enjoy the poolside bar, 2 outdoor pools, and WiFi. Vacation Village in the Berkshires: Enjoy the bar, free breakfast, and free WiFi. The Yankee, Trademark Collection by Wyndham: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Hotel with 3 restaurants. Enjoy the bar, free WiFi, and breakfast. The Red Lion Inn: Lodge with restaurant. Enjoy the bar, free WiFi, and free parking.
What is there to do in South Lee?
In the area, you can visit National Shrine of the Divine Mercy, Naumkeag Museum, and Berkshire Mountain Country Store, then find a cozy spot for a nightcap. Other places to see include Housatonic River and Chesterwood. South Lee is appreciated for its restaurants and local cheese shops.
When is the best time to visit South Lee?
Visiting local bars in South Lee is better when you know what the weather holds. These rainfall averages and temperatures 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 South Lee are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
How can I get to South Lee and around the area?
You might want to make the most of these transportation options in and around South Lee: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 10.2 mi (16.4 km) from the heart of the city. Otherwise, you can search for flights to 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.

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