The Cultural Heart of the Berkshires

Tanglewood (Lenox, MA) | 12 Minutes Away

The summer home of the Boston Symphony Orchestra. Whether you’re heading to the Shed for a masterpiece or picnicking on the lawn for a popular artist, Tanglewood is the quintessential Berkshire experience.

• The House Advantage: Avoid the high-traffic Lenox hotel rates. Our kitchen is fully equipped for you to prep the ultimate Tanglewood lawn picnic before you head out.
• Schedule/Tickets for 2026 Season:   Tanglewood 2026

Jacob’s Pillow (Becket, MA) | 15 Minutes Away

A National Historic Landmark and the epicenter of international dance. Nestled in the woods of Becket, the Pillow offers world-class performances in a stunning rustic setting.

• The House Advantage: Located right between Lenox and Becket, we are the ideal "middle ground" for guests attending multi-day festivals or traveling with performers.
• Schedule/Tickets for 2026 Season:  Jacob's Pillow

Shakespeare & Company (Lenox, MA) | 10 Minutes Away

One of the largest Shakespeare festivals in the country. From classic plays to contemporary works, their indoor and outdoor stages offer incredible theater all summer long.

• The House Advantage: Catch a late performance and be back in the comfort of your 5-bedroom retreat in just 10 minutes.

• Schedule/Tickets for 2026 Season:  Shakespeare & Company

Norman Rockwell Museum (Stockbridge, MA) | 8 Minutes Away

Home to the world's largest collection of original Rockwell art. Located on a beautiful 36-acre site overlooking the Housatonic River.

• The House Advantage: Located just one town over, you can visit the museum in the morning and be back in Lee for lunch at a local bistro by noon.

• Schedule/Tickets: Norman Rockwell Museum