Bars & Lounges

Some say that nightlife in the Berkshires has long been hard to come by. We are happy to report that this is no longer the case. Whether you're looking for an extensive beer list to conquer, the best place to get a cocktail, laid back atmosphere, or nightly live music, the Berkshires checks off all the boxes.

Date Night Dinner Spots: Pittsfield

Check out our favorite date night spots in downtown Pittsfield that offer our favorite apps, entertainment a little romance and of course, fun!

Get Inspired

Where To Stay

Yankee Inn

Newly Renovated & 100% Solar powered lodging with distant mountain views and relaxing outdoor pool
Holiday Inn Express & Suites Pittsfield | Berkshires

Opening this summer! Discover the brand-new Holiday Inn Express Pittsfield, where fresh, vibrant style meets comfort, and unbeatable convenience in the heart of the Berkshires.
The Black Swan Inn

Wake up to waterfront views during your Berkshires vacation. Located minutes from downtown Lee and Lenox

Sustainable Stays, Unforgettable Days
Escape to a one-of-a-kind, 100% solar-powered gem in Lenox—family-owned, full of charm, and the ultimate destination for an unforgettable family getaway!
Stay in Style - at the Berkshires' newest hotel
Experience modern comfort and vibrant design at the all-new Holiday Inn Express Pittsfield – Berkshires.
Lakeside R&R
Stay on the waterfront with gorgeous views of Laurel Lake
Mountain views and space to roam
This local gem offers abundant green space to roam during your Berkshires vacation.