The Berkshires Beach Vacations
Book a Beach Hotel + Flight or Car together to unlock savings
Top Beach vacation packages in The Berkshires
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Reviewed on Oct 10, 2025
3 Night Beach vacations in The Berkshires
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Reviewed on Oct 10, 2025
4 Night Beach vacations in The Berkshires
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Reviewed on Oct 24, 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Reviewed on Oct 10, 2025
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Reviewed on Oct 18, 2025
Find your perfect The Berkshires beach vacation
How do I book the best The Berkshires beach vacation packages?
Life’s a beach when you dive into our brilliant The Berkshires beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.
How can I find cheap beach vacations in The Berkshires?
A rental steps from the shore creates an amazingly affordable The Berkshires beach vacation. Seaside sojourns during low season start from $556. Prices and availability are subject to change. Additional terms may apply.
How can I book the best family beach vacations in The Berkshires?
With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.
How do I find a The Berkshires beachfront vacation?
Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.
Can I book a package including a The Berkshires vacation beach house rental?
Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.
Can I find The Berkshires beach vacation deals?
Sort your search results by deals to delight in amazing The Berkshires beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.
Can I book a The Berkshires beach trip with free cancellation and/or flexible dates?
Just like the The Berkshires tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.
Why should I book my The Berkshires beach vacation with Expedia?
Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in The Berkshires. (OK, maybe not that last part.)
Top Beach The Berkshires Hotels
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Our room was clean as a pin and we loved the option of daily maid service. Love that there’s a closet with adequate hangers, extra blanket, clock, and the shampoo, body wash dispensers in the shower. Towels were big and fluffy. LOVE the heat lamp in the bathroom!
Reviewed on Oct 23, 2025
Lakehouse Inn
Lovely setting on a lake. Friendly staff. Nice breakfast. Peaceful
Reviewed on Oct 6, 2025
Pilgrim Inn
The temperature was fine. Noticed no hot water at the sink but fine in the shower. Used both the microwave and the mini refrigerator. Appreciated both and the table to eat at. A room with twin beds for a solo traveler would save the housekeeper having to remake a 3/4 unused king bed! The Pilgrim ...
Reviewed on Sep 27, 2025
