Top Beach vacation packages in Western Massachusetts

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

Lakehouse Inn

per person

Oct 22 - Oct 25

found 12 hours ago

Roundtrip flight included

Dallas (DFW) to Albany (ALB)

9.6/10 Exceptional! (276 reviews)

This is a fantastic spot. Kurt and his staff are great. It was everything we wanted for a trip to the Berkshires.

Reviewed on Jul 16, 2025

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

per person

Oct 22 - Oct 25

found 12 hours ago

Roundtrip flight included

Dallas (DFW) to Albany (ALB)

9.2/10 Wonderful! (105 reviews)

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3 Night Beach vacations in Western Massachusetts

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

Lakehouse Inn

per person

Oct 22 - Oct 25

found 12 hours ago

Roundtrip flight included

Dallas (DFW) to Albany (ALB)

9.6/10 Exceptional! (276 reviews)

This is a fantastic spot. Kurt and his staff are great. It was everything we wanted for a trip to the Berkshires.

Reviewed on Jul 16, 2025

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

per person

Oct 22 - Oct 25

found 12 hours ago

Roundtrip flight included

Dallas (DFW) to Albany (ALB)

9.2/10 Wonderful! (105 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Western Massachusetts

View all trips

4 Night Beach vacations in Western Massachusetts

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

Fairfield Inn & Suites Springfield Holyoke

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

San Juan (SJU) to Boston (BOS)

9.2/10 Wonderful! (547 reviews)

The room was fantastic. Slept great in a strange bed for the first night I was away from home. And the staff were all so pleasant - always saying hello or checking that all was good for me. Would totally recommend this place to my friends.

Reviewed on Aug 16, 2025

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See all available trips from Columbus to Western Massachusetts

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How do I book the best Western Massachusetts beach vacation packages?

Life’s a beach when you dive into our brilliant Western Massachusetts 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 Western Massachusetts?

A rental steps from the shore creates an amazingly affordable Western Massachusetts beach vacation. Seaside sojourns during low season start from $594. Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in Western Massachusetts?

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 Western Massachusetts 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 Western Massachusetts 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 Western Massachusetts beach vacation deals?

Sort your search results by deals to delight in amazing Western Massachusetts 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 Western Massachusetts beach trip with free cancellation and/or flexible dates?

Just like the Western Massachusetts 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 Western Massachusetts 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 Western Massachusetts. (OK, maybe not that last part.)

Top Beach Western Massachusetts Hotels

Fairfield Inn & Suites Springfield Holyoke

229 Whiting Farms Road, Holyoke, MA

23 min drive from Six Flags New England

Book a stay at this business-friendly hotel in Holyoke. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...

9.2/10 Wonderful! (557 reviews)

"Room was nice clean pool was small though"

Reviewed on Aug 16, 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection

435 Laurel St, Lee, MA

51 min drive from Six Flags New England

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)

"We had great stay at The Black Swan! Very clean, great communication and excellent service. Bonuses - a beautiful lake view with lake access and a fantastic restaurant!"

Reviewed on Aug 15, 2025

Holiday Inn Express Ludlow by IHG

321 Center St, Ludlow, MA

22 min drive from Six Flags New England

Make the most of this fantastic location, as you'll be close to Haviland Pond Beach with a vacation stay at this hotel.

8.8/10 Excellent! (946 reviews)

"My" place

"Housekeepers are great, room clean, they are very accommodating Front desk very helpful and friendly Come to the area often, wouldnt stay anywhere else"

Reviewed on Aug 14, 2025

See all 1,480 properties in Western Massachusetts

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.