The Berkshires Beach Vacations 2026

Photo by Photo courtesy of Berkshire Visitors Bureau

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Top Beach vacation packages in The Berkshires

Price found within the past 48 hours. Click for updated prices.

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

$1,009

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Kansas City (MCI) to Albany (ALB)

9.2/10 Wonderful! (118 reviews)

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See all available trips from Columbus to The Berkshires

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3 Night Beach vacations in The Berkshires

Price found within the past 48 hours. Click for updated prices.

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

$1,009

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Kansas City (MCI) to Albany (ALB)

9.2/10 Wonderful! (118 reviews)

Don't see what you're looking for?

See all available trips from Columbus to The Berkshires

View all trips

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 $1,009. 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

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 ...

Sunset Inn

150 Housatonic Street Lee MA

9 min drive from Tanglewood Music Center

Make the most of this fantastic location, as you'll be near the beach when booking a getaway at this motel. Amenities at Sunset Inn include a seasonal outdoor ...

7.6/10 Good! (446 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...

"We were in town for a show at Tanglewood in Lenox. Concert had been rescheduled with little notice; so it put us in a tight spot with no time to add time to being in the Berkshires. I just looked for an inexpensive overnight to just sleep before heading back home the following morning. I wasn't expecting ..."

Reviewed on Sep 21, 2026

Pleasant Valley Motel West Stockbridge

42 Stockbridge Rd West Stockbridge MA

5 min drive from Tanglewood Music Center

Enjoy sunsets on the beach in West Stockbridge, as you'll be close to the beach when booking a stay at this motel.

6.8/10 (1,000 reviews)

"The room was fairly clean, but the wallpaper is peeling away from the wall. The towel hanging on the towel rod had dark gray streaks like it had already been used."

Reviewed on Sep 26, 2026

See all 1,096 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.