The Berkshires Beach Holidays

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Photo by Photo courtesy of Berkshire Visitors Bureau
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Find your perfect The Berkshires beach holiday

How can I book the best beach holidays in The Berkshires?

Sometimes all you want is to kick back with the sun on your face and your toes in the sand. Plus-size the blissful on your The Berkshires beach holiday by checking out the best bays and using our neighbourhood filter to find accommodation nearby – or even with serene sea views. Use the reviews and our guest-rating filter to find the loveliest options.

Can I book cheap beach holidays in The Berkshires?

For a budget beach break, consider staying a little further away from the sea, or choose self-catering rather than a hotel. You can use our amenities filter and map view to find the best cheap deals for you. Sunbathe for less with our affordable The Berkshires beach holidays, which start from . Prices and availability are subject to change. Additional terms may apply.

When can I go on a quiet beach holiday in The Berkshires?

Enjoy out-of-season seclusion on a beach holiday to The Berkshires during the quieter months. With fewer crowds competing for accommodation, you could bag a great deal, too.

Why should I book family holidays in The Berkshires with beach access?

If you have kids, beach holidays are more buckets and spades, lilos and sun cream than they are spa, cocktails and long reads – unless you book a holiday with beach access. It’s a family win. Even better, once the kids are in bed, you can sit on your bedroom balcony, listen to the waves and share a local tipple and stay in earshot of your sleeping beauties.

How can I find a The Berkshires beachfront holiday?

For the ultimate beach holiday, use our beachfront and sea view filters to whittle down your search results to find the perfect property, right on the water.

How can I book last-minute The Berkshires beach holidays?

Add a little spontaneity to your beach holiday by looking for a last-minute deal in The Berkshires. If you have set dates, pop them into the search and see what heaven awaits in just a few days.

Can I find The Berkshires beach holidays which are all inclusive?

A beach holiday to The Berkshires is one of the best occasions to treat yourself to an all-inclusive holiday package. Savour every sip of cocktail, every moment of sunshine, every blissful meal you didn’t have to cook yourself. And all included in the price. Just use our all-inclusive filter to see what’s available.

Can I book a The Berkshires beach trip with free cancellation and/or flexible dates?

Even if plans change, you don’t have to lose out. Use our filters to find accommodation with free cancellation, or even filter for buy now, pay later options. Once you’ve booked, log into your account to see all the details.

Why should I book a The Berkshires beach holiday with Expedia?

Our huge range of accommodation and flights mean you’ll find the best beach holidays in The Berkshires on Expedia in just a few clicks. It’s as easy as falling asleep to the sounds of the sea.

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! (1,003 reviews)
"Great place on a pretty lake in the Berkshires"

Reviewed on 7 Jul 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! (270 reviews)
"excellent all around"

Reviewed on 13 Jul 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. Flight-inclusive packages are ATOL protected.