Photo by Photo courtesy of Berkshire Visitors Bureau

Plan, book, travel with confidence
Better together
Save up to ₩1,660,000 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! (1,005 reviews)

Breakfast was ok. It was difficult to adjust room temp. Very inconvenient to take luggage to second floor for seniors. There should be a lif.

Reviewed on May 8, 2026

Chesapeake Inn of Lenox

210 West Street 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 ...

7.4/10 Good! (8 reviews)

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

Book a stay at this 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! (299 reviews)

Staff wonderful, homemade breakfasts, outstanding experience!

Reviewed on Apr 12, 2026

See all 1,123 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.