Cuttyhunk Beach Vacations 2026

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Top Beach vacation packages in Cuttyhunk

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

Harbor View Hotel

$1,791

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Faraway Martha's Vineyard

$1,887

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip flight included

Boston (BOS) 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* Beach vacations in Cuttyhunk

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

Harbor View Hotel

$1,791

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Cuttyhunk

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3 Night Beach vacations in Cuttyhunk

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

Harbor View Hotel

$1,459

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Faraway Martha's Vineyard

$1,649

per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Vineyard Haven (MVY)

9/10 Wonderful! (1,002 reviews)

Reviewed on Aug 20, 2026

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4 Night Beach vacations in Cuttyhunk

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

Morgan Hotel

$1,304

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Vineyard Haven (MVY)

8.6/10 Excellent! (255 reviews)

Excellent customer service . Lovely rooms . Great location

Reviewed on Sep 4, 2026

Harbor View Hotel

$1,791

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

The Christopher, The Edgartown Collection

$1,578

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Vineyard Haven (MVY)

9.8/10 Exceptional! (273 reviews)

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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 $1,304. Prices and availability are subject to change. Additional terms may apply.

When should I book a Cuttyhunk beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

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.)