A lake surrounded by autumn-colored trees.

Southeast Massachusetts Beach Vacations

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Top Beach vacation packages in Southeast Massachusetts

Price found within the past 48 hours. Click for updated prices.
  • Jan 27 - Jan 31

    Admiralty Inn & Suites - a Red Collection Hotel + Flight

    East Falmouth
    4 nights
    3.0 star property
    8.6/10 - Excellent (578 reviews)
    Roundtrip • Chicago (ORD) - Boston (BOS)
    ORD - BOS • Nonstop BOS - ORD • Nonstop
    $559
    $495
    per traveler
    found 10 hours ago
    Admiralty Inn & Suites - a Red Collection Hotel
  • Jan 27 - Jan 31

    Vineyard Harbor Motel - Private Beach + Flight

    Vineyard Haven
    4 nights
    2.5 star property
    9.0/10 - Wonderful (841 reviews)
    Roundtrip • Chicago (ORD) - Vineyard Haven (MVY)
    ORD - BOS • Nonstop BOS - ORD • Nonstop
    $840
    $639
    per traveler
    found 10 hours ago
    Vineyard Harbor Motel - Private Beach
  • Jan 27 - Jan 31

    Iris Hotel Cape Cod + Flight

    Falmouth
    4 nights
    3.0 star property
    8.4/10 - Very good (440 reviews)
    Roundtrip • Chicago (ORD) - Boston (BOS)
    ORD - BOS • Nonstop BOS - ORD • Nonstop
    $644
    $495
    per traveler
    found 10 hours ago
    Iris Hotel Cape Cod
  • Jan 27 - Jan 31

    Falmouth Tides + Flight

    Falmouth Heights
    4 nights
    3.0 star property
    9.2/10 - Wonderful (781 reviews)
    Roundtrip • Chicago (ORD) - Boston (BOS)
    ORD - BOS • Nonstop BOS - ORD • Nonstop
    $829
    $699
    per traveler
    found 10 hours ago
    Falmouth Tides
  • Feb 5 - Feb 7

    Best Western Rockland + Flight

    Rockland
    2 nights
    2.5 star property
    8.0/10 - Very good (1,009 reviews)
    Roundtrip • San Juan (SJU) - Boston (BOS)
    SJU - BOS • Nonstop BOS - SJU • Nonstop
    $592
    $563
    per traveler
    found 1 day ago
    Best Western Rockland

Discover the most popular places to visit in Southeast Massachusetts

What to do in Southeast Massachusetts

Top Beach Southeast Massachusetts Hotels

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.

Find your perfect Southeast Massachusetts beach vacation

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 $495. 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.)