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

Cuttyhunk Adventure Vacations

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Top Adventure 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 (701 reviews)
    "Couldn’t want a better location, on the beach, comfortable chairs to watch the boats come and go. Room could use updated but was clean and enjoyed."
    Reviewed July 23, 2026
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - MVY • 1 stop MVY - ATL • 1 stop
    $951
    $789
    per traveler
    found 10 hours 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 10 hours ago
    The Franklin Hotel Martha's Vineyard
  • 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 10 hours ago
    The Richard, The Edgartown Collection
  • Lobby
    Oct 7 - Oct 11

    Morgan Hotel + Flight

    Oak Bluffs
    4 nights
    2.5 star property
    8.6/10 - Excellent (241 reviews)
    Roundtrip • Atlanta (ATL) - Vineyard Haven (MVY)
    ATL - MVY • 1 stop MVY - ATL • 1 stop
    $1,328
    $1,105
    per traveler
    found 10 hours ago
    Morgan Hotel
  • Condo | Laptop workspace, WiFi (free), individually decorated
    Oct 7 - Oct 11

    The Island Inn on Martha's Vineyard + Flight

    Oak Bluffs
    4 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 - MVY • 1 stop MVY - ATL • 1 stop
    $1,182
    $985
    per traveler
    found 10 hours ago
    The Island Inn on Martha's Vineyard

Find awesome Cuttyhunk adventure vacations

How can I book the best Cuttyhunk adventure trips?

Choose your own adventure in Cuttyhunk, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.

How can I plan the perfect Cuttyhunk family adventure vacation?

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Cuttyhunk. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.

Can I book all-inclusive Cuttyhunk adventure vacation packages?

By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.

Why should I book a Cuttyhunk adventure vacation for couples?

Book a Cuttyhunk couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.

How can I find the best deals on adventure packages in Cuttyhunk?

It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.

Can I book an adventure vacation package in Cuttyhunk with free cancellation and/or flexible dates?

Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.

Why should I book a Cuttyhunk adventure trip with Expedia?

Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A.

What types of mountain accommodations are available in Cuttyhunk?

5-star hotels, cozy mountain lodges, and quaint bed and breakfasts are some of the most popular types of mountain accommodations for your vacation to Cuttyhunk. Don't forget to use the filters to home in the amenities you'd like to have, too. Maybe it's a spacious suite with a mountain view or a traditional lobby with a fireplace—you'll find it all with Expedia's easy-to-use search wizard and wide choice of accommodation.