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A coastal landscape with a sandy beach, grassy areas, and a small island with a lighthouse.

Cuttyhunk Beach Vacations

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Top Beach vacation packages in Cuttyhunk

Price found within the past 48 hours. Click for updated prices.
  • Front of property
    Sep 10 - Sep 13

    The Attleboro House + Flight

    Oak Bluffs
    3 nights
    2.5 star property
    9.8/10 - Exceptional (101 reviews)
    "The property sits where all the action is. The room is very clean however the bed mattress gave us severe back problems. The mattress needs to be change because we were stuck in the middle like a taco. The host flipped it but the mattresses needed to be replaced. The property is straight to the point with needing somewhere to sleep and bathe and the host was lovely but to save my back maybe not."
    Reviewed July 16, 2026
    Roundtrip • Washington (DCA) - Vineyard Haven (MVY)
    DCA - BOS • Nonstop BOS - DCA • Nonstop
    $664
    $547
    per traveler
    found 1 day ago
    The Attleboro House
  • Exterior
    Sep 10 - Sep 13

    The Franklin Hotel Martha's Vineyard + Flight

    Edgartown
    3 nights
    2.0 star property
    9.2/10 - Wonderful (199 reviews)
    "Sweet place"
    Reviewed July 27, 2026
    Roundtrip • Washington (DCA) - Vineyard Haven (MVY)
    DCA - BOS • Nonstop BOS - DCA • Nonstop
    Save 100% on your flight
    $1,538
    $1,011
    per traveler
    found 1 day ago
    The Franklin Hotel Martha's Vineyard
  • Condo | Laptop workspace, WiFi (free), individually decorated
    Sep 10 - Sep 13

    The Island Inn on Martha's Vineyard + Flight

    Oak Bluffs
    3 nights
    2.5 star property
    8.2/10 - Very Good (41 reviews)
    Roundtrip • Washington (DCA) - Vineyard Haven (MVY)
    DCA - BOS • Nonstop BOS - DCA • Nonstop
    Save 100% on your flight
    $940
    $699
    per traveler
    found 1 day ago
    The Island Inn on Martha's Vineyard
  • 36-inch flat-screen TV with cable channels, TV
    Sep 10 - Sep 13

    Harbor View Hotel + Flight

    Edgartown
    3 nights
    5.0 star property
    8.8/10 - Excellent (1,001 reviews)
    Roundtrip • Washington (DCA) - Vineyard Haven (MVY)
    DCA - BOS • Nonstop BOS - DCA • Nonstop
    Save 100% on your flight
    $2,800
    $2,189
    per traveler
    found 1 day ago
    Harbor View Hotel
  • Courtyard view
    Sep 10 - Sep 13

    Vineyard Harbor Motel - Private Beach + Flight

    Vineyard Haven
    3 nights
    2.5 star property
    9.0/10 - Wonderful (709 reviews)
    Roundtrip • Washington (DCA) - Vineyard Haven (MVY)
    DCA - BOS • Nonstop BOS - DCA • Nonstop
    Save 100% on your flight
    $961
    $761
    per traveler
    found 1 day ago
    Vineyard Harbor Motel - Private Beach

Find your perfect Cuttyhunk beach vacation

How do I book the best Cuttyhunk beach vacation packages?

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

A rental steps from the shore creates an amazingly affordable Cuttyhunk beach vacation. Seaside sojourns during low season start from $547. Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in Cuttyhunk?

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 Cuttyhunk 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 Cuttyhunk 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 Cuttyhunk beach vacation deals?

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

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