An aerial view of a coastal area with a lighthouse, a sandy beach, and a marina.

Chappaquiddick Island Vacations from $1,197

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The Latest Chappaquiddick Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • An indoor swimming pool with a brick wall, a white table with chairs, and a large window.
    Dec 13 - Dec 19

    Courtyard Resort + Flight

    Hyannis
    6 nights
    2.0 star property
    8.6/10 - Excellent (170 reviews)
    "Room was clean, staff were always helpful and friendly, location of hotel was ideal for local amenities, safe for solo travellers. Would definitely recommend."
    Reviewed November 5, 2026
    Roundtrip • Houston (IAH) - Hyannis (HYA)
    IAH - HYA • 1 stop HYA - IAH • 1 stop
    $1,275
    $1,197
    per traveler
    found 7 hours ago
    Courtyard Resort
  • A patio with a wooden table and chairs, a hanging flower pot with red and yellow flowers, and a view of the sea with boats in the background.
    Dec 13 - Dec 19

    Vineyard Harbor Motel - Private Beach + Flight

    Vineyard Haven
    6 nights
    2.5 star property
    9.0/10 - Wonderful (841 reviews)
    Roundtrip • Houston (IAH) - Vineyard Haven (MVY)
    IAH - HYA • 1 stop HYA - IAH • 1 stop
    $1,698
    $1,502
    per traveler
    found 7 hours ago
    Vineyard Harbor Motel - Private Beach
  • A row of wicker chairs with cushions, a map on the wall, and a view of the outside through a window.
    Dec 13 - Dec 19

    Anchor In Distinctive Waterfront Lodging + Flight

    Hyannis
    6 nights
    3.0 star property
    9.4/10 - Exceptional (1,006 reviews)
    Roundtrip • Houston (IAH) - Hyannis (HYA)
    IAH - HYA • 1 stop HYA - IAH • 1 stop
    $1,358
    $1,262
    per traveler
    found 7 hours ago
    Anchor In Distinctive Waterfront Lodging
  • A spacious living area with a dining table, sofas, and a view of the sea.
    Dec 13 - Dec 19

    Harbor View Hotel + Flight

    Edgartown
    6 nights
    5.0 star property
    8.8/10 - Excellent (1,000 reviews)
    "Loved the heated saltwater pool. Was disappointed there was not comfortable sitting in the room, esp on a rainy day or not feeling well, and watching a movie. Was surprised no elevator and we were on the third floor. The “grab and go” breakfast option was no more than a few pastries. That was disappointing. For early departure to catch ferry at 0530, no coffee was available."
    Reviewed October 22, 2026
    Roundtrip • Houston (IAH) - Vineyard Haven (MVY)
    IAH - HYA • 1 stop HYA - IAH • 1 stop
    $1,893
    $1,773
    per traveler
    found 7 hours ago
    Harbor View Hotel
  • An indoor water park with slides, a pirate-themed ship, and a sign reading "Pirate Bay".
    Dec 13 - Dec 19

    Margaritaville Resort Cape Cod + Flight

    Hyannis
    6 nights
    4.0 star property
    8.6/10 - Excellent (809 reviews)
    Roundtrip • Houston (IAH) - Hyannis (HYA)
    IAH - HYA • 1 stop HYA - IAH • 1 stop
    $1,446
    $1,372
    per traveler
    found 7 hours ago
    Margaritaville Resort Cape Cod

Chappaquiddick Island Hotel Deals

A bedroom with a bed, bedside tables, a chair, a table, and a view of the outdoors.

The Coonamessett

The Coonamessett
3.5 star property
14.7 mi from Chappaquiddick Island
8.8 out of 10, Excellent, (723 reviews)
$91 nightly
The price is $104
Nov 30 - Dec 1
Total with taxes and fees
The Coonamessett
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.
See all properties in Chappaquiddick Island
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.