Chappaquiddick Island Beach Vacations
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Top Beach vacation packages in Chappaquiddick Island
Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Cape Cod
Price was $1,118, price is now $844 per person
$844
per person
Jul 17 - Jul 20
found 17 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Hyannis (HYA)
8.8/10 Excellent! (590 reviews)
First time attending Margaritaville with my family for my son’s birthday and it was amazing. The water park experience was great. Unfortunately it was raining so we were unable to use the outdoor pool. Loved the s’mores setup they had for guest to cozy up next to the fireplace with a delicious treat. The outdoor space was relaxing and I loved that they had game setup outside for kids and adults. All and all my kids really enjoyed the stay, from my 11 year old birthday boy to my 23 year old. The island vibes, along with the friendly and welcoming staff really elevated our experience! I would definitely recommend and I plan to return with my family and friends.
Reviewed on May 30, 2026
Faraway Martha's Vineyard
Save 100% on your flight
Price was $3,937, price is now $3,202 per person
$3,202
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Vineyard Haven (MVY)
9/10 Wonderful! (1,003 reviews)
Just came back from our stay here and have to say that we were a bit disappointed. This is definitely not one of the cheaper options to stay at on the island and so we had high hopes when we booked our stay. We've been coming to the Vineyard for years and have stayed at a number of different establishments. This was by far the biggest disappointment. That being said, it wasn't all bad. I feel like if given the opportunity they might be able to change our opinions as the facelift they gave to the place was amazing and definitely had a luxury feel to the place, but at their price point I would sooner try another place first.
- Check in took 3 hours for our room to be ready even though they told us that the room was already cleaned and just needed to be inspected
- Cleanliness at the pool was hit or miss, some days there would be people cleaning up old glasses and towels left behind, other days it was a mess
- No elevator which wasn't an issue to us though we did have to carry our bags up three flights of stairs because they were short staffed
- Our door never fully closed on it's own so we had to remember to slam it each time
- No coffee in room which is fine but to not offer a decaf option or non-milk based creamers didn't exactly line up with their luxury aesthetic
- Couldn't get hot water in our room, luke warm at best, chalked it up to old pipes in an old building
- Be cautious if you stay in a room facing the Pelican club as they play loud music up to 11 p.m.
Reviewed on Jun 10, 2026
Wequassett Resort and Golf Club
Save 100% on your flight
Price was $5,705, price is now $4,746 per person
$4,746
per person
Aug 14 - Aug 19
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Hyannis (HYA)
9.4/10 Exceptional! (251 reviews)
This place is the best prettiest most wonderful place on Cape Cod! The gardens are spectacular! The pool beautiful and all restaurants exceptional!
Reviewed on Jun 4, 2026
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View all trips5* Beach vacations in Chappaquiddick Island
Price found within the past 48 hours. Click for updated prices.
Wequassett Resort and Golf Club
Save 100% on your flight
Price was $5,705, price is now $4,746 per person
$4,746
per person
Aug 14 - Aug 19
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Hyannis (HYA)
9.4/10 Exceptional! (251 reviews)
This place is the best prettiest most wonderful place on Cape Cod! The gardens are spectacular! The pool beautiful and all restaurants exceptional!
Reviewed on Jun 4, 2026
Don't see what you're looking for?
See all available trips from Columbus to Chappaquiddick Island
View all trips3 Night Beach vacations in Chappaquiddick Island
Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Cape Cod
Price was $1,118, price is now $844 per person
$844
per person
Jul 17 - Jul 20
found 17 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Hyannis (HYA)
8.8/10 Excellent! (590 reviews)
First time attending Margaritaville with my family for my son’s birthday and it was amazing. The water park experience was great. Unfortunately it was raining so we were unable to use the outdoor pool. Loved the s’mores setup they had for guest to cozy up next to the fireplace with a delicious treat. The outdoor space was relaxing and I loved that they had game setup outside for kids and adults. All and all my kids really enjoyed the stay, from my 11 year old birthday boy to my 23 year old. The island vibes, along with the friendly and welcoming staff really elevated our experience! I would definitely recommend and I plan to return with my family and friends.
Reviewed on May 30, 2026
Don't see what you're looking for?
See all available trips from Columbus to Chappaquiddick Island
View all trips4 Night Beach vacations in Chappaquiddick Island
Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Cape Cod
Price was $1,423, price is now $1,130 per person
$1,130
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Hyannis (HYA)
8.8/10 Excellent! (590 reviews)
First time attending Margaritaville with my family for my son’s birthday and it was amazing. The water park experience was great. Unfortunately it was raining so we were unable to use the outdoor pool. Loved the s’mores setup they had for guest to cozy up next to the fireplace with a delicious treat. The outdoor space was relaxing and I loved that they had game setup outside for kids and adults. All and all my kids really enjoyed the stay, from my 11 year old birthday boy to my 23 year old. The island vibes, along with the friendly and welcoming staff really elevated our experience! I would definitely recommend and I plan to return with my family and friends.
Reviewed on May 30, 2026
The Franklin Hotel Martha's Vineyard
Save 100% on your flight
Price was $2,473, price is now $1,862 per person
$1,862
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Vineyard Haven (MVY)
9.2/10 Wonderful! (192 reviews)
Was upstairs attic type bedroom But small and very clean. Excellent shower. Issue was when we went out the first night for a wedding and returned the dirt to the building was locked. Had received no indication how to open it. When I called they answered right away and was fine. Didn’t see anyone at reception the 3 days 2 nights i was there
Reviewed on Jun 7, 2026
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View all tripsFind your perfect Chappaquiddick Island beach vacation
How do I book the best Chappaquiddick Island beach vacation packages?
Life’s a beach when you dive into our brilliant Chappaquiddick Island 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 Chappaquiddick Island?
A rental steps from the shore creates an amazingly affordable Chappaquiddick Island beach vacation. Seaside sojourns during low season start from $844. Prices and availability are subject to change. Additional terms may apply.
When should I book a Chappaquiddick Island 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 Chappaquiddick Island?
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 Chappaquiddick Island 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 Chappaquiddick Island 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 Chappaquiddick Island beach vacation deals?
Sort your search results by deals to delight in amazing Chappaquiddick Island 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 Chappaquiddick Island beach trip with free cancellation and/or flexible dates?
Just like the Chappaquiddick Island 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 Chappaquiddick Island 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 Chappaquiddick Island. (OK, maybe not that last part.)
Top Beach Chappaquiddick Island Hotels
Chappy Summer Cabin!
Edgartown MA
Stay at this cottage in Edgartown. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Mytoi Garden and Chappaquidick Dike Bridge are located ...
8.4/10 Very Good! (36 reviews)
"The house is well maintained. Check-in was very easy. The house is located in the woods in a bit of a labyrinth of small roads. The kitchen facilities were great. Craig had recently purchased a new set of pots and pans that were in excellent condition. Craig was extremely helpful and welcoming. Everything ..."
Reviewed on Aug 11, 2025
Chappy cottage with private beach
Edgartown MA
Stay at this cottage in Edgartown. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chappaquidick Dike Bridge and Mytoi Garden are located ...
10/10 Exceptional! (17 reviews)
"What a gorgeous location, my family and I had a wonderful time on Chappy, will definitely be back!"
Reviewed on Sep 30, 2025
CHAPPAQUIDDICK REDUCED JUNE/JULY SPECTAC WATERVIEW, W/BEACH KAYAK/BIKES FERRY TX
Edgartown MA
Watch the sunset on the beach in Edgartown, as you'll be within walking distance of Wasque Beach when booking a stay at this vacation home. Beach towels and ...
9.6/10 Exceptional! (41 reviews)
Travelers like: on the beach, sun loungers, beach towels
Travelers say...
"Beautiful home on Chappy with everything we needed - and more - for a wonderfully relaxing, two-week vacation. Walk to the nearby beach, take the ferry into Edgartown for dinner or shopping, visit the beautiful Japanese garden on the island, and admire the incredible view and spectacular sunsets. ..."
Reviewed on Oct 24, 2025
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.
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.
