Chappaquiddick Island Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Chappaquiddick Island Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Cape Cod
$935
per person
Sep 29 - Oct 4
found 6 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
Book a stay at this spa resort in Hyannis. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the clean rooms in our reviews. Popular attractions Main Street Hyannis and Hyannis Harbor are located nearby.
Chapter House
$1,111
per person
Sep 29 - Oct 4
found 6 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
Book a stay at this historic guesthouse in Yarmouth Port. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Mayflower Beach and Cape Cod Inflatable Park are located nearby.
A beautiful inn and lovely gardens and deck to enjoy. A bar and on some nights live music makes it even better.
Reviewed on Aug 21, 2026
Anchor In Distinctive Waterfront Lodging
$1,084
per person
Sep 29 - Oct 4
found 6 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
Stay at this hotel in Hyannis. Enjoy free WiFi, an outdoor pool, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hyannis Harbor and Main Street Hyannis are located nearby.
Old , run down. Pool shut during our stay. Overall , needs a massive renovation.
Reviewed on Aug 22, 2026
Heritage House Inn on Cape Cod, an Ascend Collection Hotel
$619
per person
Sep 29 - Oct 4
found 6 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
Stay at this motel in Hyannis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Main Street Hyannis and Hyannis Harbor are located nearby.
The Villa Callo Inn
$1,229
per person
Sep 29 - Oct 4
found 6 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
Stay at this B&B in Northwest Harwich. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Cape Cod Theatre Company – Home of the Harwich Jr. Theatre and Pleasant Road Beach are located nearby.
Really enjoyed our stay. Staff went above and beyond, breakfast was top notch and the Location was great.
Reviewed on Aug 11, 2026
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See all available trips from Columbus to Chappaquiddick Island
View all tripsChappaquiddick Island Vacation Packages
Trying to plan a way to package your Chappaquiddick Island flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® Chappaquiddick Island vacation packages can help. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Chappaquiddick Island perfect. With only a few clicks, you can select the best vacation package for you and your family. AARP Travel Center has a fabulous selection of flights and lodgings, as well as local things to do to choose from.
Chappaquiddick Island Hotel Deals
You can choose from around 3401 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Chappaquiddick Island hot spots, we have plenty of options available.
We have fantastic rates on everything from family-friendly resorts that meet all the vacation must-haves to inexpensive hotels which are great for those on wanting to save a little money. You can look through our vast catalog of possibilities and choose the hotel that is ideal for you and your family. With AARP Travel Center's Chappaquiddick Island hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.
Things to do in Chappaquiddick Island
People from all over make this city their vacation destination, and with good reason. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.
Looking for more? Then Check out AARP Travel Center's "Things to Do" Page.
Package Your Chappaquiddick Island Vacation and Save
As an AARP Member, you can cash in on all the great savings. You can save on select hotels worldwide, flights, and even car rentals. No matter what vacation package you choose, you can rest easy knowing that you already saved on your trip. The hardest packing you'll have to do is for your suitcase. Book now and get ready for your Chappaquiddick Island vacation.
Top Hotel Deals
Iris Hotel Cape Cod
291 Jones Rd Falmouth MA
Book a stay at this business-friendly hotel in Falmouth. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Woods Hole Ferry Terminal ...
Sea Crest Beach Resort
350 Quaker Rd North Falmouth MA
Book a stay at this beach hotel in North Falmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Falmouth Inn
824 Main Street Falmouth MA
Book a stay at this business-friendly hotel in Falmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Hyannis Harbor Hotel
213 Ocean St Hyannis MA
Book a stay at this business-friendly hotel in Hyannis. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Our guests praise the helpful staff in our ...
Summercamp
70 Lake Avenue Oak Bluffs MA
Book a stay at this beach hotel in Oak Bluffs. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
The Beachside
30 North Beach Street Nantucket MA
Stay at this hotel in Nantucket. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Jethro Coffin House and Children's Beach are located ...
AutoCamp Cape Cod
836 Palmer Avenue Falmouth MA
Stay at this holiday park in Falmouth. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff in our reviews. Popular ...
Hyannis Plaza Hotel
662 Main Street Hyannis MA
Book a stay at this luxury hotel in Hyannis. Enjoy free parking, an outdoor pool, and a 24-hour front desk. Popular attractions Cape Cod Melody Tent and Main ...
Vineyard Harbor Motel - Private Beach
60 Beach Road Vineyard Haven MA
Book a stay at this beach motel in Vineyard Haven. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms ...
Heritage House Inn on Cape Cod, an Ascend Collection Hotel
540 Old Colony Rd Hyannis MA
Stay at this motel in Hyannis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Main ...
Americas Best Value Inn & Suites Hyannis Cape Cod
206 Main St Hyannis MA
Stay at this hotel in Hyannis. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms and the overall value in our reviews. Popular ...
Admiralty Inn & Suites - a Red Collection Hotel
51 Teaticket Highway East Falmouth MA
Book a stay at this business-friendly hotel in East Falmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Comfort Inn Hyannis - Cape Cod
259 Main Street Hyannis MA
Book a stay at this business-friendly hotel in Hyannis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Ocean Street Inn on Hyannis Harbor
131 Ocean St Hyannis MA
Stay at this motel in Hyannis. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Popular attractions Hyannis Harbor and Main Street Hyannis are located ...
Inn on the Square
40 North Main Street Falmouth MA
Stay at this hotel in Falmouth. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular ...
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See all available properties in Chappaquiddick Island
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, Sep 14 - Thu, Oct 1
LGA
LaGuardia
ACK
Nantucket Memorial
$247
Roundtrip
found 16 hours ago
Sun, Aug 30 - Mon, Aug 31
BOS
Logan Intl.
HYA
Barnstable Municipal
$360
Roundtrip
found 1 hour ago
Wed, Sep 9 - Thu, Sep 17
EWR
Newark Liberty Intl. Airport
ACK
Nantucket Memorial
$407
Roundtrip
found 5 days ago
Sun, Aug 30 - Wed, Sep 2
JFK
John F. Kennedy Intl.
MVY
Martha's Vineyard
$447
Roundtrip
found 4 days ago
Sun, Aug 30 - Wed, Sep 2
JFK
John F. Kennedy Intl.
MVY
Martha's Vineyard
$546
Roundtrip
found 4 days ago
Best points of interest in Edgartown
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