Cuttyhunk Adventure Vacations 2026

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Top Adventure vacation packages in Cuttyhunk

Price found within the past 48 hours. Click for updated prices.

Harbor View Hotel

$1,844

per person

Oct 8 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,004 reviews)

Faraway Martha's Vineyard

$3,066

per person

Oct 14 - Oct 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Vineyard Haven (MVY)

9/10 Wonderful! (1,002 reviews)

I enjoyed my stay in the Chappy House – Room 409, a suite with its on entrance from the outside. It was very well appointed and similar to a spacious one bedroom apartment without the kitchen. Must be capable of maneuvering stone pathways and steps to access it. Very nice for a long-term stay. I’d be interested in purchasing one! (Luxury vinyl plank flooring needs repairing in one hallway spot — barely noticeable.) 🙂

Reviewed on Aug 20, 2026

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5* Adventure vacations in Cuttyhunk

Price found within the past 48 hours. Click for updated prices.

Harbor View Hotel

$1,844

per person

Oct 8 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,004 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Cuttyhunk

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3 Night Adventure vacations in Cuttyhunk

Price found within the past 48 hours. Click for updated prices.

Faraway Martha's Vineyard

$583

per person

Nov 5 - Nov 8

found 6 hours ago

Roundtrip flight included

New York (LGA) to Vineyard Haven (MVY)

9/10 Wonderful! (1,002 reviews)

Reviewed on Aug 20, 2026

Harbor View Hotel

$703

per person

Nov 5 - Nov 8

found 6 hours ago

Roundtrip flight included

New York (LGA) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,004 reviews)

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See all available trips from Columbus to Cuttyhunk

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4 Night Adventure vacations in Cuttyhunk

Price found within the past 48 hours. Click for updated prices.

Morgan Hotel

$1,295

per person

Nov 5 - Nov 9

found 19 hours ago

Roundtrip flight included

Atlanta (ATL) to Vineyard Haven (MVY)

8.6/10 Excellent! (253 reviews)

Front desk was helpful and kind, front entrance door can be noisy when opening and closing.

Reviewed on Sep 1, 2026

Faraway Martha's Vineyard

$1,412

per person

Nov 5 - Nov 9

found 19 hours ago

Roundtrip flight included

Atlanta (ATL) to Vineyard Haven (MVY)

9/10 Wonderful! (1,002 reviews)

Reviewed on Aug 20, 2026

Harbor View Hotel

$1,575

per person

Nov 5 - Nov 9

found 19 hours ago

Roundtrip flight included

Atlanta (ATL) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,004 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Cuttyhunk

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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.