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

Chappaquiddick Island Vacations from $710

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The Latest Chappaquiddick Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A row of wicker chairs with cushions, a map on the wall, and a view of the outside through a window.
    Jan 22 - Jan 26

    Anchor In Distinctive Waterfront Lodging + Flight

    Hyannis
    4 nights
    3.0 star property
    9.4/10 - Exceptional (1,006 reviews)
    Roundtrip • Boston (BOS) - Hyannis (HYA)
    BOS - HYA • 1 stop HYA - BOS • 1 stop
    $821
    $710
    per traveler
    found 14 hours ago
    Anchor In Distinctive Waterfront Lodging
  • A patio area with two Adirondack chairs facing a view of the sea, a picnic table, and a tree.
    Jan 22 - Jan 26

    Vineyard Harbor Motel - Private Beach + Flight

    Vineyard Haven
    4 nights
    2.5 star property
    9.0/10 - Wonderful (840 reviews)
    Roundtrip • Boston (BOS) - Vineyard Haven (MVY)
    BOS - HYA • 1 stop HYA - BOS • 1 stop
    $1,011
    $861
    per traveler
    found 14 hours ago
    Vineyard Harbor Motel - Private Beach
  • Room
    Jan 22 - Jan 26

    The Island Inn on Martha's Vineyard + Flight

    Oak Bluffs
    4 nights
    2.5 star property
    8.4/10 - Very good (63 reviews)
    Roundtrip • Boston (BOS) - Hyannis (HYA)
    BOS - HYA • 1 stop HYA - BOS • 1 stop
    $1,216
    $1,073
    per traveler
    found 14 hours ago
    The Island Inn on Martha's Vineyard
  • A bedroom with a large bed, a view of the outdoors through sliding glass doors, and a balcony with a white railing.
    Jan 22 - Jan 26

    Faraway Martha's Vineyard + Flight

    Edgartown
    4 nights
    4.0 star property
    9.0/10 - Wonderful (1,007 reviews)
    "Overall excellent option right in downtown Edgartown. Beautifully decorated. Extremely clean. Service was impeccable. The two bedroom option is amazing. decorated with class and spacious overlooking the pool and views to the bay."
    Reviewed November 4, 2026
    Roundtrip • Boston (BOS) - Vineyard Haven (MVY)
    BOS - HYA • 1 stop HYA - BOS • 1 stop
    $1,157
    $1,024
    per traveler
    found 14 hours ago
    Faraway Martha's Vineyard
  • A spacious lobby with a large blue mural, comfortable seating areas, and a prominent circular floor design.
    Jan 22 - Jan 26

    Margaritaville Resort Cape Cod + Flight

    Hyannis
    4 nights
    4.0 star property
    8.6/10 - Excellent (808 reviews)
    "Perfect"
    Reviewed November 7, 2026
    Roundtrip • Boston (BOS) - Hyannis (HYA)
    BOS - HYA • 1 stop HYA - BOS • 1 stop
    $941
    $853
    per traveler
    found 14 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)
$104 nightly
The price is $119
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.