Chappaquiddick Island Beach Vacations

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Flight and Beach hotel deals in Chappaquiddick Island

Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

CA $1,392
per person
Oct 9 - Oct 12
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
8.6/10 Excellent! (733 reviews)
Clean room, parking Great family trip

Reviewed on Sep 7, 2026

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3 Night Beach holidays in Chappaquiddick Island

Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

CA $1,392
per person
Oct 9 - Oct 12
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
8.6/10 Excellent! (733 reviews)
Clean room, parking Great family trip

Reviewed on Sep 7, 2026

Don't see what you're looking for?
See all available trips from Columbus to Chappaquiddick Island
View all trips

Find the best beach vacations in Chappaquiddick Island

What are some benefits when booking beach vacations in Chappaquiddick Island?

When you travel to the beach in Chappaquiddick Island, 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 Chappaquiddick Island?

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 Chappaquiddick Island 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 Chappaquiddick Island?

There are quite a few things you can do to get cheap beach vacations in Chappaquiddick Island. Prices range from CA $1,392, 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 Chappaquiddick Island. These package deals let you save by booking your accommodation and your flight together with savings of up to 13.

Why should I book family beach vacations?

When you're travelling with the family to Chappaquiddick Island, 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 Chappaquiddick Island?

It's easy to find a beachfront vacation accommodation in Chappaquiddick Island 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 Chappaquiddick Island 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 Chappaquiddick Island 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 Edgartown. 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.

Beach Hotels in Chappaquiddick Island

BIG DISCOUNT CHAPPY WEEK OCT 10-17 SPECTAC WATERWV WALK-BCH KAYAK/BIKE, FERRY TX

BIG DISCOUNT CHAPPY WEEK OCT 10-17 SPECTAC WATERWV WALK-BCH KAYAK/BIKE, FERRY TX

Edgartown MA
  • 27 min walk from Chappaquidick Dike Bridge
Book a stay at this beach vacation home in Edgartown. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Wasque Beach and Norton Point Beach ...
9.6/10 Exceptional! (43 reviews)
"The view is grand, it overlooks the southern portion of Katama Bay across to Norton Point: beautiful sunsets! It’s a very Chappy experience, down a dirt road into a quiet and private grouping of homes of all different styles nestled in the “woods. Continue on the road and you reach a wide expanse ..."

Reviewed on Sep 1, 2026

BIG DISCOUNT CHAPPY WEEK OCT 10-17 SPECTAC WATERWV WALK-BCH KAYAK/BIKE, FERRY TX
Sleeps 12, amazing view, tennis court, basketball court, beaches

Sleeps 12, amazing view, tennis court, basketball court, beaches

Edgartown MA
  • 4 min drive from Chappaquidick Dike Bridge
Book a stay at this family-friendly vacation home in Edgartown. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Mytoi Garden and Edgartown ...
9.6/10 Exceptional! (43 reviews)
"House was great. Looks exactly like it does in the pictures. Communication with the host was easy and she was readily available to answer any of our questions. Best part of the home was the kitchen where we spent many mornings making breakfast and congregating before we started our day. Chappy is ..."

Reviewed on Aug 11, 2026

Sleeps 12, amazing view, tennis court, basketball court, beaches
Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach

Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach

Edgartown MA
  • 20 min walk from Chappaquidick Dike Bridge
Stay at this vacation home in Edgartown. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Mytoi Garden and Chappaquidick Dike Bridge are ...
10/10 Exceptional! (40 reviews)
"Amazing stay!"

Reviewed on Jul 25, 2026

Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach
See all 3,364 properties in Chappaquiddick Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Things to do

Martha's Vineyard Self-Driving Audio Tour

Martha's Vineyard: Self-Guided Driving Audio Tour

CA $21
per traveller
Martha's Vineyard: Self-Guided Driving Audio Tour
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

CA $69
per traveller
Massachusetts: Smartphone-Based Audio Tour Bundle
Marthas Vineyard Luxury Tour

Marthas Vineyard Luxury Tour (2hrs)

CA $761
per traveller
Marthas Vineyard Luxury Tour (2hrs)
See all activities in Chappaquiddick Island

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.