Chappaquiddick Island Vacation Packages
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Top Chappaquiddick Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Anchor In Distinctive Waterfront Lodging
CA $1,568
per person
Oct 7 - Oct 12
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
9.4/10 Exceptional! (1,006 reviews)
We loved staying at the Anchor In! Set overlooking the harbor, it was a perfect getaway, close enough to the town of Hyannis, yet far enough from the hustle and bustle of tourists during peak season. Dale who managed the breakfast area was friendly and helpful in advising local excursions. The breakfast offered a selection of cereals, fruit, muffins, bagels and breakfast sandwiches. In addition an assortment of drinks, yogurts and snack bars were available. Coffee and cookies were available late into the night to enjoy around their fire pit.Beautiful flowers surrounded their swimming pool. Mary Kay greeted us with a smile at the front desk and called us when our room was available. ( We arrived by 10 am) All in all a wonderful stay, we would highly recommend this resort!
Reviewed on Aug 21, 2026
Inn on Main
CA $1,992
per person
Oct 7 - Oct 12
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
10/10 Exceptional! (78 reviews)
Very accommodating hosts , Dave & Ruta. Delicious 2 course breakfast.Room was clean, very comfortable and great amenities. Hosts were very helpful regarding dining and touring ideas. Highly recommend
Reviewed on Aug 8, 2026
Ready to book your vacation to Chappaquiddick Island?
Chappaquiddick Island Hotel Deals
Iris Hotel Cape Cod
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
CA $187
CA $215 total
Sep 7 - Sep 8
includes taxes & fees
8.4/10 Very good! (351 reviews)
"I have tried three hotels now in the Falmouth area, and all have been disappointing, but I have never stayed at such a filthy, unkempt property as the Iris. Walking to our room, we noticed the landscaping has been left to rot in the sun. Room numbers are printed on pieces of paper taped to the walls, ..."
Reviewed on Aug 21, 2026
Sea Crest Beach Resort
350 Quaker Rd North Falmouth MA
Fully refundableReserve now, pay when you stay
CA $362
CA $493 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (443 reviews)
"Everything was excellent, but the last three times we've been there ( every year we book two rooms for 1 week in August) check-in is supposed to be at four and for past three years we've had to wait until almost 6 PM. I just can't understand it. They make you leave at 11 o'clock in the morning on ..."
Reviewed on Aug 21, 2026
Falmouth Inn
824 Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
CA $171
CA $223 total
Sep 14 - Sep 15
includes taxes & fees
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.
What to do in Chappaquiddick Island
Martha's Vineyard: Self-Guided Driving Audio Tour
CA $21
per traveller
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
CA $70
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
CA $71
per traveller
Frequently asked questions
How much does a Chappaquiddick Island vacation package cost?
Say yes to new adventures with our Chappaquiddick Island vacation packages, which start from just CA $917. Choose the flights and hotels that suit your travel style. Then, add on a couple of tours or experiences for an unforgettable escape.
How do I get a cheap travel package to Chappaquiddick Island?
Combine your flights and hotels, throw in extras such as tours, and save with a Chappaquiddick Island vacation package. You won't just enjoy amazing discounts on your adventure — you'll have loads of choice within your reach too. When you book through Expedia, you'll have your pick of over 550 partner airlines and 1,000,000 properties all over the world. Your next epic adventure begins right here, right now!
How far in advance should I book my Chappaquiddick Island vacation?
Travelers are usually able to look up international fares on Expedia within 12 months of the departure date. Booking last minute? With a stroke of luck, it's still possible to purchase a cheaper ticket only weeks before your flight.
What does an Expedia Chappaquiddick Island travel package include?
Expedia has all you need to book your Chappaquiddick Island getaway, but how you structure your package is your call. Select from any combination of rental cars, flights and hotels. Looking for some activities or tours to fill in your time? Once you've made your booking, you can add them too. No matter your budget or style, there's a vacation package to meet your needs.
What should I know before booking a Chappaquiddick Island travel package?
We already have low prices. However, you'll enjoy an even better deal if you book your flights, hotels and car rentals together. With an Expedia package, you'll get transparent pricing and a great range of choice.
Can I choose my airline with a Chappaquiddick Island Expedia vacation package?
With a vacation package, you're always in charge. Whether you're eager to fly to Chappaquiddick Island in coach or first class, simply choose from the available airline options. Expedia has access to more than 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Chappaquiddick Island vacation package?
We totally understand — life doesn't always go according to plan. If you've booked a Chappaquiddick Island vacation package and have to change or cancel it, we can help. We suggest taking a look at our Customer Service Portal first for information. But generally speaking, if you've taken out your package in the last 24 hours, you may be able to cancel and rebook for free. If it's more than 24 hours, your hotel, airline or car rental company may charge a fee.
Explore a world of travel with Expedia
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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.
