Southeast Massachusetts Beach Vacations 2026

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Top Beach vacation packages in Southeast Massachusetts

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

The Mansion at Ocean Edge

$896

per person

Nov 22 - Nov 27

found 16 hours ago

Roundtrip flight included

Los Angeles (LAX) to Boston (BOS)

8.2/10 Very Good! (1,006 reviews)

Harbor View Hotel

$1,529

per person

Dec 17 - Dec 21

found 1 day ago

Roundtrip flight included

Houston (IAH) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Beautiful Hotel and Venue with impeccable amenities. Beautiful water views and outstanding and friendly Staff. Disappointed we were not able to stay longer. Will definitely plan another trip in the near future!

Reviewed on Oct 10, 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

$1,529

per person

Dec 17 - Dec 21

found 1 day ago

Roundtrip flight included

Houston (IAH) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Reviewed on Oct 10, 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

$1,506

per person

Nov 11 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Cincinnati (CVG) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Reviewed on Oct 10, 2026

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4 Night Beach vacations in Southeast Massachusetts

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

Sea Crest Beach Resort

$557

per person

Nov 12 - Nov 16

found 1 day ago

Roundtrip flight included

Austin (AUS) to Boston (BOS)

7.6/10 Good! (522 reviews)

Chatham Tides

$1,068

per person

Dec 18 - Dec 22

found 1 day ago

Roundtrip flight included

Houston (IAH) to Boston (BOS)

9.4/10 Exceptional! (778 reviews)

Beautiful ocean views, clean room with comfortable bed and bedding. Staff was welcoming and helpful. Location was convenient and safe. Would stay here again.

Reviewed on Oct 12, 2026

By the Sea Guests Bed & Breakfast & Suites

$721

per person

Nov 12 - Nov 16

found 1 day ago

Roundtrip flight included

Austin (AUS) to Boston (BOS)

9.2/10 Wonderful! (245 reviews)

We stayed in the suites. Large comfortable room, great kitchen. Location was good, everything in Dennis Port is close by. Loved being that close to the water. Price was good for off season. My spouse would have enjoyed a TV in the bedroom and a few complimentary coffee pods. May benefit from some shelves in the bathroom to place things on. Only hang up we had was that we were told the keys would be in the blue mailbox since we got in late at night and there would be no staff on the property. The keys were not left outside the suites in the mailbox. Tried to communicate by text with staff and had no call back. Also tried chat with Hotels.com that was no help with the specific problem. After about 15-20’ we found the envelope with our keys in a different mailbox at the building where the regular rooms are ( we thought we were going to have to sleep in the car)!😅

Reviewed on Oct 11, 2026

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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 $557. Prices and availability are subject to change. Additional terms may apply.

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 ...

8.8/10 Excellent! (341 reviews)

Travelers like: on the beach, sun loungers, beach umbrellas, beach towels

Travelers say...

"Beautiful property, view of the ocean. Fireplace is very nice amenity."

Reviewed on Oct 12, 2026

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! (870 reviews)

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

Travelers say...

"Chatham Bars Inn is undoubtedly in a prime location and has all of the ingredients to be a great hotel. However, we stayed recently in the main building and the room (whilst ok) was very average, it looked tired and in need of a refurbishment - the bed in particular was disappointing and very uncomfortable ..."

Reviewed on Oct 8, 2026

See all 11,289 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.