Berkshire County Travel Guide
Massachusetts





Popular cities in Berkshire County
Lenox
Known for Live music, Entertainment and Museums
A dream destination for those who love all things artistic, this upscale town is known for hosting the world-famous Tanglewood Music Festival.
Reasons to visit
- Tanglewood Music Center
- The Mount
- Wyndhurst Golf & Club
Pittsfield
Known for Entertainment, Theatres and Sports
Located at a fork in the Housatonic River, this city provides an appealing mix of cultural diversions and outdoor pursuits.
Reasons to visit
- Bousquet Ski Area
- Hancock Shaker Village
- Berkshire Museum
Williamstown
Known for Universities, Museums and Theatres
With culture, small-town charm and beautiful mountain scenery, this lively college town in the Berkshires is a very popular destination.
Reasons to visit
- Williams College
- The Clark Art Institute
Great Barrington
Known for Dining, Hiking and Live music
Enjoy fine dining and antique shopping at this Berkshires hub, along with hiking, biking and skiing in the surrounding countryside.
Reasons to visit
- Lake Mansfield Park
- Monument Mountain Reservation
Lee
Known for Shopping, Museums and Scenery
This picturesque town has plenty of family-friendly activities and is ideally placed for exploring the largest forest in the state.
Reasons to visit
- Goose Pond Reservation
Stockbridge
Known for Historical, Museums and Romantic
Get away to romantic Stockbridge! Enjoy the gardens, camping and bars.
Reasons to visit
- Norman Rockwell Museum
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- 5 Star Hotels in Cheshire
- Hotels near Animagic Museum of Animation
- Guest Houses in Ashuwillticook Rail Trail
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- Dalton Hotels
- Hancock Hotels
- Hinsdale Hotels
- Hotels near Jiminy Peak Mountain Resort
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- B&B in Lee
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- Lee Hotels
- B&B in Lenox
- Adults Only Resorts & in Lenox
- Cheap Hotels in Lenox
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- Luxury Hotels in Lenox
- Lenox Hotels
- New Ashford Hotels
- Lodges in October Mountain State Forest
- Peru Hotels
- Cheap Hotels in Pittsfield
- Pittsfield Hotels
- Richmond Hotels
- South Lee Hotels
- B&B in Stockbridge
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- Stockbridge Hotels
- Hotels near Tanglewood Music Center
- Washington Hotels
- Gay-Friendly Hotels in West Stockbridge
- West Stockbridge Hotels
- Windsor Hotels
- Flights to Cheshire
- Flights to Lanesborough
- Flights to Lee
- Flights to Lenox
- Flights to Pittsfield
- Flights to Stockbridge
- Flights from Stockbridge
- Flights from Peru
- Flights from Hinsdale
- Flights from Windsor
- Flights from Lee
- Flights from Lenox
- Flights from Pittsfield
- Flights from New York (JFK) to Pittsfield (PSF)
- Visit Amherst
- Ashuwillticook Rail Trail Holidays
- Visit Ashuwillticook Rail Trail
- Visit Becket
- Visit Blandford
- Visit Cheshire
- Visit Colrain
- Visit Cummington
- Visit East Longmeadow
- Visit Goshen
- Visit Great Barrington
- Visit Greenfield
- Hancock Holidays
- Visit Hancock
- Hoffman's Pottery
- Lanesborough Holidays
- Lenox Holidays
- Visit Lenox
- Visit Longmeadow
- Visit Mill River
- New Ashford Holidays
- Norman Rockwell Museum
- Visit North Adams
- Visit Northampton
- Visit Orange
- Visit Pittsfield
- Visit Sandisfield
- Visit Shelburne Falls
- Visit Southampton
- Visit Springfield
- Visit Stockbridge
- Visit Sunderland
- Tanglewood Music Center
- Visit The Berkshires
- Visit Turners Falls
- Ventfort Hall Mansion and Gilded Age Museum
- Visit West Stockbridge
- Visit Western Massachusetts
- Visit Williamstown
- Windsor Holidays

