Southeast Massachusetts Beach Vacations 2026

Top Beach vacation packages in Southeast Massachusetts

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

Harbor View Hotel

$1,577

per person

Nov 27 - Nov 30

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Loved the heated saltwater pool. Was disappointed there was not comfortable sitting in the room, esp on a rainy day or not feeling well, and watching a movie. Was surprised no elevator and we were on the third floor. The “grab and go” breakfast option was no more than a few pastries. That was disappointing. For early departure to catch ferry at 0530, no coffee was available.

Reviewed on Oct 22, 2026

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5* Beach vacations in Southeast Massachusetts

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

Harbor View Hotel

$1,577

per person

Nov 27 - Nov 30

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Reviewed on Oct 22, 2026

Don't see what you're looking for?

See all available trips from Columbus to Southeast Massachusetts

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3 Night Beach vacations in Southeast Massachusetts

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

Harbor View Hotel

$1,577

per person

Nov 27 - Nov 30

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Reviewed on Oct 22, 2026

Don't see what you're looking for?

See all available trips from Columbus to Southeast Massachusetts

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4 Night Beach vacations in Southeast Massachusetts

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

Bluegreen Vacations The Soundings, an Ascend Collection Resort

$566

per person

Dec 31 - Jan 4

found 1 day ago

Roundtrip non-stop flight included

White Plains (HPN) to Boston (BOS)

8.8/10 Excellent! (404 reviews)

Everything at this hotel is what I want in a beachside resort. Easy access to the beach, outdoor pool, inside pool and outside hot tub. Kitchenette and fireplace. This was my 3rd stay and I will be back.

Reviewed on Oct 7, 2026

Harbor Hotel Provincetown

Save 100% on your flight

$16,223

per person

Dec 31 - Jan 4

found 1 day ago

Roundtrip non-stop flight included

White Plains (HPN) to Provincetown (PVC)

8.4/10 Very Good! (1,003 reviews)

Sea Crest Beach Resort

$809

per person

Jan 14 - Jan 18

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Boston (BOS)

7.6/10 Good! (522 reviews)

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

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

A rental steps from the shore creates an amazingly affordable Southeast Massachusetts beach vacation. Seaside sojourns during low season start from $566. Prices and availability are subject to change. Additional terms may apply.

When should I book a Southeast Massachusetts 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 Southeast 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 Southeast 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 Southeast 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 Southeast Massachusetts beach vacation deals?

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

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

Top Beach Southeast Massachusetts Hotels

Sea Crest Beach Resort

350 Quaker Rd North Falmouth MA

2 hours drive from Gillette Stadium

At this hotel, get ready to enjoy the sunsets on the beach in North Falmouth, as you'll be near Cape Cod Beaches. 2 restaurants, a private beach, and a beach ...

Lighthouse Inn

1 Lighthouse Inn Rd West Dennis MA

2 hours drive from Gillette Stadium

Make the most of this fantastic location, as you'll be a short walk from Cape Cod Beaches with a holiday at this hotel. Amenities at Lighthouse Inn include a ...

Chatham Bars Inn

297 Shore Rd Chatham MA

2 hours drive from Gillette Stadium

Settle in and relax at this luxury boutique resort and get ready to stroll along the shore in Chatham, as you'll be a short walk from Cape Cod Beaches. 3 outdoor ...

9.2/10 Wonderful! (873 reviews)

Travelers like: on the beach, cabanas, beach bars, beach umbrellas

Travelers say...

"Amazing property and staff."

Reviewed on Oct 18, 2026

See all 11,221 properties in Southeast 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.