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

$827

per person

Feb 14 - Feb 18

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

9.2/10 Wonderful! (110 reviews)

It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on Oct 27, 2025

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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

$783

per person

Apr 8 - Apr 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Albany (ALB)

9.2/10 Wonderful! (110 reviews)

It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on Oct 27, 2025

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4 Night Beach vacations in The Berkshires

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

Quality Inn

$436

per person

Feb 14 - Feb 18

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

8.4/10 Very Good! (1,000 reviews)

Great place to stay if you enjoy paying less money and still sleeping well. Inexpensive, clean, quiet, and ridiculously convenient—just a short two-block stroll to the downtown strip for shopping and restaurants (close enough to walk, far enough to avoid the noise). Only 2.5 miles down a local road to Butternut ski mountain, so you’ll be on the slopes before your coffee fully kicks in. CVS shares the same parking lot, which is perfect in case you forget toothpaste, sunscreen, or your dignity. Most importantly—and let’s be honest, this matters—a beer, wine, liquor, and cheese shop is only one mile down the road. Priorities are clearly respected here. Rooms are clean, beds are super comfortable, and the décor politely reminds you that time exists. Free breakfast is solid but not life-changing: eggs, toast, sausage, waffles, yogurt, coffee, fruit—everything you need to function, nothing you’ll write poetry about. Bathroom fans are loud, but they drown out the 1 time per day freight train in the back yard, so net positive. Overall, a great stay, and for the cheap nightly price, it’s basically unbeatable unless you’re expecting chandeliers and a personal butler. Enjoy!

Reviewed on Jan 11, 2026

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

$827

per person

Feb 14 - Feb 18

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

9.2/10 Wonderful! (110 reviews)

It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on Oct 27, 2025

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

$823

per person

Feb 14 - Feb 18

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

9.4/10 Exceptional! (754 reviews)

Temperature of pool was cold

Reviewed on Jan 1, 2026

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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

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

Pilgrim Inn

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

Lakehouse Inn

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

See all 1,067 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.