The Berkshires Beach Holidays

Book a Beach Hotel + Flight or Car together to unlock savings

Photo by Photo courtesy of Berkshire Visitors Bureau
  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to ₹43,962 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Top Beach The Berkshires Hotels

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3 out of 5
435 Laurel St, Lee, MA
  • 5 min drive from Tanglewood Music Center
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the restaurant in their reviews. Popular ...
9/10 Wonderful! (1,008 reviews)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful"

Reviewed on 18 Aug 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
Chesapeake Inn of Lenox

Chesapeake Inn of Lenox

3 out of 5
210 West Street, P.O. Box 1920, Lenox, MA
  • 2 min walk from Tanglewood Music Center
Stay at this 3-star golf B&B in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Tanglewood Music Center and Frelinghuysen Morris ...

Travellers like: near the beach, outdoor pool

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

Reviewed on 14 Oct 2019

Chesapeake Inn of Lenox
Lakehouse Inn

Lakehouse Inn

4 out of 5
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 Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
9.6/10 Exceptional! (277 reviews)
"Welcoming Hostess, but was told room servicing would be limited due to staff shortage. Excellent breakfast. Boating equipment was in poor shape. Many items were unusable. Lawn chairs and outdoor gathering areas were very good. Disappointed with refrigerator size in room. Nice bottle of wine in room. ..."

Reviewed on 3 Aug 2025

Lakehouse Inn
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.