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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
    Aug 28 - Aug 31

    Vineyard Harbor Motel - Private Beach + Flight

    Vineyard Haven
    3 nights
    2.5 star property
    9.0/10 - Wonderful (691 reviews)
    "We had a wonderful stay! The room was clean, comfortable, and the location was perfect. It was close to Oak Bluffs, making it easy to walk to the shops, restaurants, the harbor, and many of the island’s attractions. The front desk clerk was absolutely amazing friendly, welcoming, and full of great recommendations that helped us make the most of our time on Martha’s Vineyard. Overall, we had a fantastic stay and would definitely stay here again!"
    Reviewed July 20, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - MVY • 1 stop MVY - ATL • 1 stop
    $1,217
    $952
    per traveler
    found 1 day ago
    Vineyard Harbor Motel - Private Beach
  • Exterior
    Sep 17 - Sep 20

    The Franklin Hotel Martha's Vineyard + Flight

    Edgartown
    3 nights
    2.0 star property
    9.2/10 - Wonderful (197 reviews)
    "We had a great stay at the Franklin. It was a beautiful property and the design was well thought out. Great location and staff was kind and welcoming. Loved that they had beach chairs to use too! Will definitely be back."
    Reviewed July 19, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - ACK • 1 stop ACK - ATL • 1 stop
    $1,880
    $1,542
    per traveler
    found 1 day ago
    The Franklin Hotel Martha's Vineyard
  • Premium bedding, in-room safe, blackout drapes
    Aug 28 - Aug 31

    The Richard, The Edgartown Collection + Flight

    Edgartown
    3 nights
    3.5 star property
    9.6/10 - Exceptional (191 reviews)
    "Just spent a few days at The Richard in Edgartown and it was just wonderful! It’s a beautiful boutique hotel in a great location and I would absolutely recommend a stay there. My room was beautiful and well designed. The bed was super comfy. The bathroom was a great size and well appointed. I had everything I needed for my stay. The main areas and outdoors were also amazing. I enjoyed my time in the back garden which is just gorgeously landscaped with great seating options. Lastly, the..."
    Reviewed July 19, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - MVY • 1 stop MVY - ATL • 1 stop
    $1,842
    $1,540
    per traveler
    found 1 day ago
    The Richard, The Edgartown Collection
  • Lobby
    Aug 28 - Aug 31

    Morgan Hotel + Flight

    Oak Bluffs
    3 nights
    2.5 star property
    8.6/10 - Excellent (239 reviews)
    "Clean and convenient location"
    Reviewed July 20, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - MVY • 1 stop MVY - ATL • 1 stop
    $1,486
    $1,252
    per traveler
    found 1 day ago
    Morgan Hotel
  • Condo | WiFi (free), bed sheets
    Sep 17 - Sep 20

    The Island Inn on Martha's Vineyard + Flight

    Oak Bluffs
    3 nights
    2.5 star property
    8.2/10 - Very Good (40 reviews)
    "We stayed in the townhouse. Plenty of room, 2bd and 2bths. Living with fireplace, deck and kitchen. Love the modern country decor. High ceilings with large wood beams. Would definitely stay again!"
    Reviewed July 1, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - ACK • 1 stop ACK - ATL • 1 stop
    $1,580
    $1,371
    per traveler
    found 1 day ago
    The Island Inn on Martha's Vineyard

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 $952. 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.)