Chappaquiddick Island Vacation Packages 2026 from $426

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The Latest Chappaquiddick Island vacation packages

Price found within the past 48 hours. Click for updated prices.

Courtyard Resort

$426

per person

Oct 30 - Nov 3

found 3 hours ago

Roundtrip flight included

Nashville (BNA) to Hyannis (HYA)

8.6/10 Excellent! (124 reviews)

Property is tired. Needs an ipgrade

Reviewed on Sep 15, 2026

The Christopher, The Edgartown Collection

$769

per person

Oct 16 - Oct 18

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Vineyard Haven (MVY)

9.8/10 Exceptional! (274 reviews)

Place was so cute and quaint!

Reviewed on Sep 6, 2026

Harbor View Hotel

$709

per person

Oct 16 - Oct 18

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

The Island Inn on Martha's Vineyard

$619

per person

Oct 16 - Oct 18

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Vineyard Haven (MVY)

8.4/10 Very Good! (53 reviews)

The worst place we stayed at. The bed was broken and we had to sleep on living room couch…the bathroom doors didn’t look and one bathroom door didn’t close. We complained to front desk in person next day but were not much help and didn’t even bother to change room forget about the upgrade for the inconvenience. It’s nice property but not being maintained by staff and staff not really there to help as they are just there to do minimum and collect their check!

Reviewed on Sep 10, 2026

Anchor In Distinctive Waterfront Lodging

$532

per person

Oct 30 - Nov 3

found 3 hours ago

Roundtrip flight included

Nashville (BNA) to Hyannis (HYA)

9.4/10 Exceptional! (1,005 reviews)

Great place, friendly staff, nice breakfast. Gorgeous view, and comfortable bed.

Reviewed on Sep 12, 2026

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What to do in Chappaquiddick Island

Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

$50

per traveler

Martha's Vineyard Private 4 hour Tour for groups up to 6 people

$700

per traveler

Marthas Vineyard Luxury Tour (2hrs)

$550

per traveler

See all activities in Chappaquiddick Island

Chappaquiddick Island Hotel Deals

Sea Crest Beach Resort

350 Quaker Rd North Falmouth MA

$245 nightly

$280 total

Oct 12 - Oct 13

Total with taxes and fees

7.6/10 Good! (501 reviews)

"Honestly, I didn’t like anything about it, we checked in and when we started going up the main stairs the stair boards some were broken and almost felt like we were going to fall backwards. Then when we got to our room, immediately we noticed that the handle lock for the door that divides each bedroom ..."

Reviewed on Sep 15, 2026

Iris Hotel Cape Cod

291 Jones Rd Falmouth MA

Fully refundableReserve now, pay when you stay

$133 nightly

$152 total

Oct 12 - Oct 13

Total with taxes and fees

Hyannis Harbor Hotel

213 Ocean St Hyannis MA

Fully refundableReserve now, pay when you stay

$219 nightly

$250 total

Oct 12 - Oct 13

Total with taxes and fees

8.2/10 Very Good! (1,013 reviews)

"Parking sucks. You i have to use your room key to get out of the parking lot every time. That's especially inconvenient when you're checking out, you can't just leave your key in the room and drive off."

Reviewed on Sep 16, 2026

See all 3,357 properties in Chappaquiddick Island

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.