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.

Faraway Martha's Vineyard

$1,660

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Vineyard Haven (MVY)

9/10 Wonderful! (1,004 reviews)

We came here on our anniversary and could not have picked a better place. The boutique-yet-full-service hotel is elegant and beautiful, with great taste everywhere and amazing ocean views. The heated (perfect temperature) pool and jacuzzi were a perfect spot to take a break at any time in the day, with relaxing and happy lounge music. Most importantly, the staff is highly well trained, educated, and devoted to service with a smile without the attitude sometimes found in premium hotels sometimes. Mattia (spelling?), Duna, Julian were amazing. Coffee in the room a great plus! Short walk from the ferry (3 minutes!) and in the center of the action makes this hard to beat. I would only add more obvious breakfast choices (most guests just go out to great options short walks away) to make this even more perfect. We will certainly be back.

Reviewed on Jul 28, 2026

Harbor View Hotel

$1,790

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

We had an amazing stay and we can not wait to be back.

Reviewed on Jul 31, 2026

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5* Adventure vacations in Cuttyhunk

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

Harbor View Hotel

$1,790

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

We had an amazing stay and we can not wait to be back.

Reviewed on Jul 31, 2026

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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

$1,660

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Vineyard Haven (MVY)

9/10 Wonderful! (1,004 reviews)

Reviewed on Jul 28, 2026

Harbor View Hotel

$1,790

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

We had an amazing stay and we can not wait to be back.

Reviewed on Jul 31, 2026

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4 Night Adventure vacations in Cuttyhunk

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

The Richard, The Edgartown Collection

$1,415

per person

Sep 21 - Sep 25

found 15 hours ago

Roundtrip flight included

Dallas (DFW) to Vineyard Haven (MVY)

9.6/10 Exceptional! (192 reviews)

The Franklin Hotel Martha's Vineyard

$1,764

per person

Sep 17 - Sep 21

found 1 day ago

Roundtrip flight included

Washington (DCA) to Vineyard Haven (MVY)

9.2/10 Wonderful! (199 reviews)

Morgan Hotel

$1,569

per person

Sep 17 - Sep 21

found 1 day ago

Roundtrip flight included

Washington (DCA) to Vineyard Haven (MVY)

8.6/10 Excellent! (243 reviews)

The first room we were in was right next to the street and lobby and was quite loud. They were very accommodating and moved us upstairs to a quiet room. Overall a great hotel with great service.

Reviewed on Aug 4, 2026

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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.