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

Harbor View Hotel

$1,345
per person
Nov 3 - Nov 7
found 7 hours ago
Roundtrip non-stop flight included
Washington (IAD) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
We always enjoy our stays at the Harbor View. The rooms are terrific and beautifully appointed, and the staff is consistently helpful and friendly. The front veranda, with its sweeping views of Edgartown Lighthouse, the Atlantic Ocean, and Chappaquiddick, is truly delightful. The on-site Bettini Restaurant is another fabulous amenity—convenient, inviting, and absolutely delicious. You simply can’t go wrong booking a stay at the Harbor View!

Reviewed on Sep 16, 2026

Faraway Martha's Vineyard

Faraway Martha's Vineyard

$1,451
per person
Dec 11 - Dec 15
found 21 hours ago
Roundtrip flight included
New York (NYC) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
A few smaller items that made the stay slightly questionable, no elevator bags had to be carried. Not much to do about that in an historical building, but it's a note for guests. I would expect a notch better, especially when coming to bedding. The bed was comfortable, but I would expect down pillows and blanket at this price point. The record player was a lovely touch. Parking was challenging, but again, historical town we must make compromises. Wonderful shower towels, GREAT pool and hot tub area. The location of the hotel is / was supreme. Only coffee offered in the lobby, no inroom machine, and no option of a latte, or capp in the hotel or lobby, only in adjacent restaurant. (Loud bathroom fan, bug in room, a little mildew build up on the shower grout, definite degradation happening on plumbing fixtures. At this price point, should be better)

Reviewed on Sep 17, 2026

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5* Beach vacations in Cuttyhunk

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

Harbor View Hotel

$1,345
per person
Nov 3 - Nov 7
found 7 hours ago
Roundtrip non-stop flight included
Washington (IAD) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
We always enjoy our stays at the Harbor View. The rooms are terrific and beautifully appointed, and the staff is consistently helpful and friendly. The front veranda, with its sweeping views of Edgartown Lighthouse, the Atlantic Ocean, and Chappaquiddick, is truly delightful. The on-site Bettini Restaurant is another fabulous amenity—convenient, inviting, and absolutely delicious. You simply can’t go wrong booking a stay at the Harbor View!

Reviewed on Sep 16, 2026

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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

$1,124
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
A few smaller items that made the stay slightly questionable, no elevator bags had to be carried. Not much to do about that in an historical building, but it's a note for guests. I would expect a notch better, especially when coming to bedding. The bed was comfortable, but I would expect down pillows and blanket at this price point. The record player was a lovely touch. Parking was challenging, but again, historical town we must make compromises. Wonderful shower towels, GREAT pool and hot tub area. The location of the hotel is / was supreme. Only coffee offered in the lobby, no inroom machine, and no option of a latte, or capp in the hotel or lobby, only in adjacent restaurant. (Loud bathroom fan, bug in room, a little mildew build up on the shower grout, definite degradation happening on plumbing fixtures. At this price point, should be better)

Reviewed on Sep 17, 2026

Harbor View Hotel

Harbor View Hotel

$1,207
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
We always enjoy our stays at the Harbor View. The rooms are terrific and beautifully appointed, and the staff is consistently helpful and friendly. The front veranda, with its sweeping views of Edgartown Lighthouse, the Atlantic Ocean, and Chappaquiddick, is truly delightful. The on-site Bettini Restaurant is another fabulous amenity—convenient, inviting, and absolutely delicious. You simply can’t go wrong booking a stay at the Harbor View!

Reviewed on Sep 16, 2026

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4 Night Beach vacations in Cuttyhunk

Price found within the past 48 hours. Click for updated prices.
The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

$1,261
per person
Dec 11 - Dec 15
found 21 hours ago
Roundtrip flight included
New York (NYC) to Vineyard Haven (MVY)
8.4/10 Very Good! (53 reviews)
Faraway Martha's Vineyard

Faraway Martha's Vineyard

$1,451
per person
Dec 11 - Dec 15
found 21 hours ago
Roundtrip flight included
New York (NYC) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
A few smaller items that made the stay slightly questionable, no elevator bags had to be carried. Not much to do about that in an historical building, but it's a note for guests. I would expect a notch better, especially when coming to bedding. The bed was comfortable, but I would expect down pillows and blanket at this price point. The record player was a lovely touch. Parking was challenging, but again, historical town we must make compromises. Wonderful shower towels, GREAT pool and hot tub area. The location of the hotel is / was supreme. Only coffee offered in the lobby, no inroom machine, and no option of a latte, or capp in the hotel or lobby, only in adjacent restaurant. (Loud bathroom fan, bug in room, a little mildew build up on the shower grout, definite degradation happening on plumbing fixtures. At this price point, should be better)

Reviewed on Sep 17, 2026

Harbor View Hotel

Harbor View Hotel

$1,345
per person
Nov 3 - Nov 7
found 7 hours ago
Roundtrip non-stop flight included
Washington (IAD) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
We always enjoy our stays at the Harbor View. The rooms are terrific and beautifully appointed, and the staff is consistently helpful and friendly. The front veranda, with its sweeping views of Edgartown Lighthouse, the Atlantic Ocean, and Chappaquiddick, is truly delightful. The on-site Bettini Restaurant is another fabulous amenity—convenient, inviting, and absolutely delicious. You simply can’t go wrong booking a stay at the Harbor View!

Reviewed on Sep 16, 2026

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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 $1,124. 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.)

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