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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.
  • Courtyard view
    Oct 7 - Oct 11

    Vineyard Harbor Motel - Private Beach + Flight

    Vineyard Haven
    4 nights
    2.5 star property
    9.0/10 - Wonderful (704 reviews)
    "TLDR we left a day early because it was not what we were hoping for. Although I know you get what you pay for, this one was sadly pretty disappointing. We paid around $280 for a studio room for three nights. This might be around the cheapest you can find in Martha’s Vineyard in the middle of the summer, but reviews and pictures made it seem pretty legit. We got there around 1pm on the ferry and walked to the motel. It’s pretty conveniently located and right on the water which is great. We..."
    Reviewed July 24, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - MVY • 1 stop MVY - ATL • 1 stop
    $951
    $789
    per traveler
    found 1 day ago
    Vineyard Harbor Motel - Private Beach
  • Exterior
    Oct 7 - Oct 11

    The Franklin Hotel Martha's Vineyard + Flight

    Edgartown
    4 nights
    2.0 star property
    9.2/10 - Wonderful (198 reviews)
    "We truly enjoyed our stay at The Franklin. The location was great, the spaces were clean and well maintained, the staff was helpful and courteous, and the room was pleasant and comfortable. The common kitchen space was convenient and a great feature. A few small nit picky things: The bathroom door in our room was not aligned properly so it was difficult to close and made quite a bit of noise, which was disturbing to a partner sleeping. Likewise, the french door leading to the rear patio on the..."
    Reviewed July 21, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - MVY • 1 stop MVY - ATL • 1 stop
    $1,379
    $1,103
    per traveler
    found 1 day ago
    The Franklin Hotel Martha's Vineyard
  • 36-inch flat-screen TV with cable channels, TV
    Sep 20 - Sep 23

    Harbor View Hotel + Flight

    Edgartown
    3 nights
    5.0 star property
    8.8/10 - Excellent (1,001 reviews)
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - BOS • Nonstop BOS - ATL • Nonstop
    Save 100% on your flight
    $1,487
    $1,195
    per traveler
    found 8 hours ago
    Harbor View Hotel
  • Front of property - evening/night
    Sep 20 - Sep 23

    The Christopher, The Edgartown Collection + Flight

    Edgartown
    3 nights
    3.0 star property
    9.8/10 - Exceptional (261 reviews)
    "Good breakfast. Great location. Darling place to stay."
    Reviewed July 22, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - BOS • Nonstop BOS - ATL • Nonstop
    Save 100% on your flight
    $1,583
    $1,294
    per traveler
    found 8 hours ago
    The Christopher, The Edgartown Collection
  • Premium bedding, in-room safe, blackout drapes
    Oct 7 - Oct 11

    The Richard, The Edgartown Collection + Flight

    Edgartown
    4 nights
    3.5 star property
    9.6/10 - Exceptional (192 reviews)
    "Great location. Clean, well maintained property. Nice staff. Our Queen bed room was comfortable but def cozy. We had a great stay."
    Reviewed July 22, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - MVY • 1 stop MVY - ATL • 1 stop
    $1,507
    $1,246
    per traveler
    found 1 day ago
    The Richard, The Edgartown Collection

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 $789. 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.)