Skip to main content
A coastal landscape with a sandy beach, grassy areas, and a small island with a lighthouse.

Cuttyhunk Beach Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Beach vacation packages in Cuttyhunk

Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Oct 4 - Oct 7

    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 • New York (EWR) - Vineyard Haven (MVY)
    EWR - MVY • 1 stop MVY - EWR • 1 stop
    $1,676
    $1,473
    per traveler
    found 3 hours ago
    The Franklin Hotel Martha's Vineyard
  • 36-inch flat-screen TV with cable channels, TV
    Oct 4 - Oct 10

    Harbor View Hotel + Flight

    Edgartown
    6 nights
    5.0 star property
    8.8/10 - Excellent (1,001 reviews)
    Roundtrip • New York (EWR) - Vineyard Haven (MVY)
    EWR - MVY • 1 stop MVY - EWR • 2 stops
    $2,982
    $2,573
    per traveler
    found 1 day ago
    Harbor View Hotel
  • Premium bedding, in-room safe, blackout drapes
    Sep 10 - Sep 13

    The Richard, The Edgartown Collection + Flight

    Edgartown
    3 nights
    3.5 star property
    9.6/10 - Exceptional (193 reviews)
    Roundtrip • New York (EWR) - Vineyard Haven (MVY)
    EWR - BOS • Nonstop BOS - EWR • Nonstop
    $1,686
    $1,491
    per traveler
    found 1 day ago
    The Richard, The Edgartown Collection
  • Terrace/patio
    Sep 18 - Sep 21

    The Edgartown Inn, The Edgartown Collection + Flight

    Edgartown
    3 nights
    3.5 star property
    9.8/10 - Exceptional (167 reviews)
    "Wow, this was truly one of the best, if not the best, hotel experiences my wife and I have ever had. We booked here for a single night to celebrate our anniversary after staying in a less nice hotel for the previous few days. Boy was this a huge upgrade! Although it was 2x the price, it was 10x the experience. We got there at around 11am on a Wednesday just to drop off our bags, but they were able to get us into our room right away. They also personally walked us to the room and asked how our..."
    Reviewed July 24, 2026
    Roundtrip • Dallas (DFW) - Vineyard Haven (MVY)
    DFW - MVY • 1 stop MVY - DFW • 1 stop
    $2,582
    $2,299
    per traveler
    found 17 hours ago
    The Edgartown Inn, The Edgartown Collection
  • Miscellaneous
    Oct 4 - Oct 10

    Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel + Flight

    Edgartown
    6 nights
    3.0 star property
    8.4/10 - Very Good (623 reviews)
    "Not worth $700 per night based on location, surroundings, and overall upkeep. It’s a motel near the town."
    Reviewed July 22, 2026
    Roundtrip • New York (EWR) - Vineyard Haven (MVY)
    EWR - MVY • 1 stop MVY - EWR • 2 stops
    $2,387
    $2,138
    per traveler
    found 1 day ago
    Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

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 $1,473. 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.)