Cuttyhunk Beach Vacations

Book a Beach Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Beach vacation packages in Cuttyhunk

Price found within the past 48 hours. Click for updated prices.
Faraway Martha's Vineyard

Faraway Martha's Vineyard

$1,559
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
Common spaces like the lobby and the pool were excellent, but those are the only good things to say about this property. Our room (104) was dark and had no privacy. There are no chests of drawers to put away clothes (they put bar glasses in them), the fixtures in the bathroom are loose and rusty and covered with water spots. There were stains on the carpet, which felt dirty, and a crack in the bathroom ceiling. The safe was too small for a standard laptop so good luck with that. There was no real hospitality to speak of as most of the time the people at the front desk do not even look up from their phones or desks to greet you when you walk by. We felt like this was a massive waste of money. On top of it all, they charged me $197 after I had left and when I called to ask what for they never answer or return messages. Never again.

Reviewed on Aug 18, 2026

Harbor View Hotel

Harbor View Hotel

$2,209
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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
View all trips

5* Beach vacations in Cuttyhunk

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

Harbor View Hotel

$2,209
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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
View all trips

3 Night Beach vacations in Cuttyhunk

Price found within the past 48 hours. Click for updated prices.
Faraway Martha's Vineyard

Faraway Martha's Vineyard

$1,559
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
Common spaces like the lobby and the pool were excellent, but those are the only good things to say about this property. Our room (104) was dark and had no privacy. There are no chests of drawers to put away clothes (they put bar glasses in them), the fixtures in the bathroom are loose and rusty and covered with water spots. There were stains on the carpet, which felt dirty, and a crack in the bathroom ceiling. The safe was too small for a standard laptop so good luck with that. There was no real hospitality to speak of as most of the time the people at the front desk do not even look up from their phones or desks to greet you when you walk by. We felt like this was a massive waste of money. On top of it all, they charged me $197 after I had left and when I called to ask what for they never answer or return messages. Never again.

Reviewed on Aug 18, 2026

Harbor View Hotel

Harbor View Hotel

$2,209
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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
View all trips

4 Night Beach vacations in Cuttyhunk

Price found within the past 48 hours. Click for updated prices.
The Sydney, The Edgartown Collection

The Sydney, The Edgartown Collection

$929
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Vineyard Haven (MVY)
9.6/10 Exceptional! (198 reviews)
Morgan Hotel

Morgan Hotel

$1,440
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Vineyard Haven (MVY)
8.6/10 Excellent! (248 reviews)
The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

$1,456
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Vineyard Haven (MVY)
9.2/10 Wonderful! (199 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Cuttyhunk
View all trips

Find your perfect Cuttyhunk beach vacation

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 $929. Prices and availability are subject to change. Additional terms may apply.

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.)

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.