Cuttyhunk Beach Vacations

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Top Beach vacation packages in Cuttyhunk

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

Harbor View Hotel

$773

per person

Mar 19 - Mar 24

found 1 day ago

Roundtrip flight included

Denver (DEN) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,000 reviews)

It was pretty quiet while we were there so the breakfast was grab and go and the restaurants were closed but everything else about the hotel and the area were great. We had a lovely room - the location is perfect and there was enough going on in the town. Shame about the rain Late November

Reviewed on Dec 2, 2025

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5* Beach vacations in Cuttyhunk

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

Harbor View Hotel

$773

per person

Mar 19 - Mar 24

found 1 day ago

Roundtrip flight included

Denver (DEN) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,000 reviews)

It was pretty quiet while we were there so the breakfast was grab and go and the restaurants were closed but everything else about the hotel and the area were great. We had a lovely room - the location is perfect and there was enough going on in the town. Shame about the rain Late November

Reviewed on Dec 2, 2025

Don't see what you're looking for?

See all available trips from Columbus to Cuttyhunk

View all trips

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 $773. 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.)