Beach Vacations in Cuttyhunk 2026

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Flight and Beach hotel deals in Cuttyhunk

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

Faraway Martha's Vineyard

CA $1,267

per person

Oct 26 - Oct 30

found 13 hours ago

Roundtrip flight included

Toronto (YTO) to Vineyard Haven (MVY)

9/10 Wonderful! (1,000 reviews)

We LOVED our stay at Faraway - the pool was amazing, staff was super helpful. They had a very convenient messaging system for requests. The staff recommended the Pelican Club for dinner, which is basically right on-site, but we tried to get in multiple times and there was always a wait! The food at their snack bar was really good for lunch. The location was incredible - it was our first time in Martha's Vineyard and we feel we got so spoiled!!

Reviewed on Aug 11, 2026

Harbor View Hotel

CA $1,389

per person

Oct 26 - Oct 30

found 13 hours ago

Roundtrip flight included

Toronto (YTO) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

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5* Beach holidays in Cuttyhunk

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

Harbor View Hotel

CA $1,389

per person

Oct 26 - Oct 30

found 13 hours ago

Roundtrip flight included

Toronto (YTO) 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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4 Night Beach holidays in Cuttyhunk

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

Morgan Hotel

CA $1,031

per person

Oct 26 - Oct 30

found 13 hours ago

Roundtrip flight included

Toronto (YTO) to Vineyard Haven (MVY)

8.6/10 Excellent! (248 reviews)

Faraway Martha's Vineyard

CA $1,267

per person

Oct 26 - Oct 30

found 13 hours ago

Roundtrip flight included

Toronto (YTO) to Vineyard Haven (MVY)

9/10 Wonderful! (1,000 reviews)

Reviewed on Aug 11, 2026

The Franklin Hotel Martha's Vineyard

CA $1,073

per person

Oct 26 - Oct 30

found 13 hours ago

Roundtrip flight included

Toronto (YTO) to Vineyard Haven (MVY)

9.2/10 Wonderful! (199 reviews)

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What are some benefits when booking beach vacations in Cuttyhunk?

When you travel to the beach in Cuttyhunk, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip.

How can I book the best beach vacations in Cuttyhunk?

To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Cuttyhunk trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit.

Can I book cheap beach vacations in Cuttyhunk?

There are quite a few things you can do to get cheap beach vacations in Cuttyhunk. Prices range from CA $1,031, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out.

Can I book beach packages?

Yes, and you'll find quite a few beach packages available in Cuttyhunk. These package deals let you save by booking your accommodation and your flight together with savings of up to 17.

Why should I book family beach vacations?

When you're travelling with the family to Cuttyhunk, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room.

How can I find a beachfront vacation in Cuttyhunk?

It's easy to find a beachfront vacation accommodation in Cuttyhunk using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline.

How can I book last-minute beach vacations?

Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Cuttyhunk as your destination and see what's available.

Can I find all-inclusive beach vacations ?

Yes, all you have to do to find all-inclusive beach vacations in Cuttyhunk is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance.

Can I book a beach trip that's fully refundable?

Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Gosnold. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too.

Why should I book beach vacations with Expedia?

When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips.