Chappaquiddick Island Vacations from $373
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The Latest Chappaquiddick Island vacation packages
Price found within the past 48 hours. Click for updated prices.
Inn on Main
Save 100% on your flight
per person
Oct 31 - Nov 3
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Hyannis (HYA)
10/10 Exceptional! (68 reviews)
What a great place! Central location made it super easy to get around. Hosts were fantastic- very nice, welcoming and very helpful with great restaurant, beach or visit recommendations. I highly recommend The Inn on Main.
Reviewed on Aug 7, 2025
Faraway Martha's Vineyard
Save 100% on your flight
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Vineyard Haven (MVY)
9/10 Wonderful! (1,003 reviews)
Beautifully decorated and nice workspace. Staff was not helpful with baggage at check-in. For the price, the toilet paper was cheap and no slippers. It was very nice that they allowed you to use the pool and property after the 11am checkout.
Reviewed on Aug 9, 2025
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View all tripsDiscover the most popular places to visit in Chappaquiddick Island
Cape Poge Lighthouse
Find out about the history of Edgartown when you spend time at Cape Poge Lighthouse. Wander the beautiful beaches and waterfront in the area.
Chappaquidick Dike Bridge
Find out about the history of Edgartown when you spend time at Chappaquidick Dike Bridge. Check out the charming coffeehouses or top-notch restaurants in this walkable area.
Mytoi Garden
Explore the great outdoors at Mytoi Garden, a lovely green space in Edgartown. Check out the wineries or charming coffeehouses in this walkable area.
What to do in Chappaquiddick Island
Massachusetts Highlights: Freedom Trail, Salem & More Tour
$50
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
$50
per traveler
New Budget Friendly Shared 4 hour African American Heritage Tour
$130
per adult
Chappaquiddick Island Hotel Deals
Hyannis Plaza Hotel
662 Main Street, Hyannis, MA
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $123 total per night from Sep 2 to Sep 3
$123 total
Sep 2 - Sep 3
Total includes taxes and fees
6.8/10 (839 reviews)
"The property was in need of an up date."
Reviewed on Aug 11, 2025
Falmouth Inn
824 Main Street, Route 28, Falmouth, MA
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $182 total per night from Sep 1 to Sep 2
$182 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (1,003 reviews)
"Thank you for great breakfasts with fresh and delicious food, especially sausages.Thank you for indoor pool, clean, warm and welcoming."
Reviewed on Aug 10, 2025
The Beachside
30 North Beach Street, Nantucket, MA
$383 nightly
The price is $428 total per night from Sep 1 to Sep 2
$428 total
Sep 1 - Sep 2
Total includes taxes and fees
9.2/10 Wonderful! (178 reviews)
"Really good stay, the kids loved all the activities like the arcade, pool, evening movies and popcorn etc..."
Reviewed on Aug 12, 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.
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- Mytoi Garden
- Chappaquidick Dike Bridge
- Norton Point Beach
- Wasque Beach
- Edgartown Lighthouse
- Edgartown Vacations
- Lighthouse Beach
- Old Whaling Church
- Vincent House Museum
- Visit Edgartown
- Where to stay in Edgartown
- Cape Poge Lighthouse
- Bend in the Road Beach
- Joseph Sylvia State Beach
- Katama Beach
- Felix Neck Wildlife Sanctuary
- Gus Ben David's World of Reptiles and Birds Park
- Dr Daniel Fisher House
- Farm Neck Golf Club
- Inkwell Beach
- Ocean Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.