The Berkshires Beach Vacations

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Top Beach vacation packages in The Berkshires

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The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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3 Night Beach vacations in The Berkshires

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The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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See all available trips from Columbus to The Berkshires
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4 Night Beach vacations in The Berkshires

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Quality Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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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 $436. Prices and availability are subject to change. Additional terms may apply.

When should I book a The Berkshires beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
  • 39 min drive from Jiminy Peak Mountain Resort
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! (1,004 reviews)
Absolutely lovely room and kind staff. Stayed in superior room with balcony, lake view and fireplace. It was the perfect respite!

Reviewed on Jan 10, 2026

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Pilgrim Inn

Pilgrim Inn

2.5 out of 5
165 Housatonic St Lee MA
  • 43 min drive from Jiminy Peak Mountain Resort
At this hotel, get ready to stroll along the shoreline in Lee, as you'll be near the beach.
5.6/10 (332 reviews)
Wonderful fantastic

Reviewed on Nov 9, 2025

Pilgrim Inn
Lakehouse Inn

Lakehouse Inn

4 out of 5
615 Laurel St. Lee MA
  • 38 min drive from Jiminy Peak Mountain Resort
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! (290 reviews)
Warm welcome. Very clean and well presented rooms. Delicious breakfast. Highly recommended.

Reviewed on Dec 8, 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.

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