Photo by Photo courtesy of Berkshire Visitors Bureau

Plan, book, travel with confidence

Better together

Save up to ₩234,741 when you book a flight and hotel together*

Find the right fit

With over 300,000 hotels worldwide, it's easy to create a perfect package

Rest easy

Plan, book, and manage your trip all in one place

Top Beach The Berkshires Hotels

The Black Swan Lee - Lenox, an Ascend Collection Hotel

435 Laurel St, Lee, MA

5 min drive from Tanglewood Music Center

At this hotel, get ready to lounge by the shoreline in Lee, as you'll be close to the beach. A restaurant and a 24-hour fitness center are just some of the amenities ...

9/10 Wonderful! (1,009 reviews)

Clean room, nice view

Reviewed on Oct 15, 2025

Chesapeake Inn of Lenox

210 West Street, P.O. Box 1920, Lenox, MA

2 min walk from Tanglewood Music Center

Feel the sand between your toes at this bed & breakfast and lounge by the shoreline in Lenox, as you'll be not far from the beach. An outdoor tennis court, an ...

Travelers like: close to beach, outdoor pool

Travelers say...

Very convenient location to arts / outdoors events in Lenox area. Available for one night stay, last minute booking. Host very responsive

Reviewed on Oct 14, 2019

Lakehouse Inn

615 Laurel St., Lee, MA

5 min drive from Tanglewood Music Center

Stay at this 4-star beach B&B in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...

9.6/10 Exceptional! (285 reviews)

Lovely setting on a lake. Friendly staff. Nice breakfast. Peaceful

Reviewed on Oct 6, 2025

See all 1,102 properties in The Berkshires

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.