Search Deals onChappaquiddick Island Vacation Packages
Chappaquiddick Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Ocean Street Inn on Hyannis Harbor
Price was $700, price is now $631 per person
$631
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Hyannis (HYA)
Stay at this motel in Hyannis. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Popular attractions Hyannis Harbor and Main Street Hyannis are located nearby.
The building on the outside was very run down. I was afraid that the floor boards on the second floor walkway would collapse. I wasn’t able to make a cup of coffee because the holder for the coffee pod was missing. Not to mention no plug close by except near the floor on an adjacent wall. Only good thing was the location, steps away from the ferry. Next time I will just pay for parking and stay elsewhere.
Reviewed on Aug 12, 2026

Chapter House
Price was $1,399, price is now $1,070 per person
$1,070
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Columbus (CMH) 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.
The Chapter House is an absolutely charming Inn with a rich history and period elegance. Our experience began with some very attentive and inviting attention from Bill, who was the manager at check-in. He had already communicated that our room was ready and he immediately made us feel at home. He took us personally to our room, which was in the Carriage House and it was cozy and completely charming with a sumptuous King bed......great sleep! What is really charming about the Chapter House are the grounds, which include a large golf-green like lawn and patio deck with ample seating and places to relax. And lastly, a six-seater bar with great drink menu and nosh, and Bill bakes the most amazing chocolate croissants! Fabulous stay and we can't wait to go back!
Reviewed on Aug 3, 2026

Wequassett Resort and Golf Club
Save 100% on your flight
Price was $2,286, price is now $1,837 per person
$1,837
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Hyannis (HYA)
Book a stay at this luxury resort in Harwich. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ocean Edge Golf Club and Harwich Port are located nearby.
Our stay at Wequassett Resort and Golf Club was nothing short of extraordinary. From the moment we arrived, we were surrounded by beauty, elegance, and exceptional hospitality.
Our Premier Waterview Cottage was absolutely breathtaking. The accommodations were beautiful, luxurious, and exceeded our expectations in every way. Waking up to the stunning waterfront views made our stay even more special.
The dining was equally impressive. Every meal was delicious, beautifully prepared, and a true reflection of the quality and care that went into every aspect of our experience.
What truly set Wequassett apart, however, was the incredible staff. Each person we encountered went above and beyond to make our 30th anniversary celebration feel truly special. Their genuine warmth, thoughtfulness, and attention to every detail made us feel incredibly welcomed and cared for.
Celebrating 30 years of marriage at such a beautiful and extraordinary resort was a memory we will treasure forever. Wequassett gave us far more than a wonderful vacation—it gave us an unforgettable celebration filled with beautiful moments, exceptional service, and memories we will cherish for years to come.
We cannot thank the entire Wequassett team enough and are already looking forward to returning. Absolutely beautiful, breathtaking, and truly unforgettable!
Reviewed on Aug 8, 2026

Inn on Main
Price was $1,259, price is now $1,042 per person
$1,042
per person
Oct 21 - Oct 25
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Hyannis (HYA)
Stay at this B&B in Yarmouth Port. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mayflower Beach and Cape Cod Inflatable Park are located nearby.
Very accommodating hosts , Dave & Ruta. Delicious 2 course breakfast.Room was clean, very comfortable and great amenities. Hosts were very helpful regarding dining and touring ideas. Highly recommend
Reviewed on Aug 8, 2026

The Villa Callo Inn
Price was $1,207, price is now $1,006 per person
$1,006
per person
Oct 21 - Oct 25
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Hyannis (HYA)
Stay at this B&B in West Harwich. Enjoy free breakfast, free WiFi, and free parking. Popular attractions West Dennis Beach and Cape Cod Inflatable Park 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

Courtyard By Marriott Cape Cod Hyannis
Price was $1,083, price is now $943 per person
$943
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Hyannis (HYA)
Book a stay at this business-friendly hotel in Hyannis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Main Street Hyannis and Cape Codder Water Park are located nearby.

Holiday Inn Hyannis by IHG
Price was $829, price is now $733 per person
$733
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Hyannis (HYA)
Stay at this hotel in Hyannis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Cape Codder Water Park and Cape Cod Melody Tent are located nearby.
Breakfast needs to pay is not free very poor on staff not enough cooks
not enough food needs to wait too long to able to eat too expensive for what they offer never anymore for us
Reviewed on Aug 12, 2026

The Richard, The Edgartown Collection
Price was $1,917, price is now $1,721 per person
$1,721
per person
Oct 2 - Oct 4
found 21 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Vineyard Haven (MVY)
Stay at this hotel in Edgartown. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Inkwell Beach and Oak Bluffs Harbor are located nearby.
Chappaquiddick Island Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Chappaquiddick Island Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sun, Aug 23 - Thu, Aug 27
DCA
Ronald Reagan Washington National
MVY
Martha's Vineyard
$230 Roundtrip, found 4 days ago
$230
Roundtrip
found 4 days ago

Sat, Sep 26 - Wed, Oct 14
BOS
Logan Intl.
ACK
Nantucket Memorial
$270 Roundtrip, just found
$270
Roundtrip
just found

Tue, Sep 15 - Fri, Oct 2
BOS
Logan Intl.
MVY
Martha's Vineyard
$310 Roundtrip, found 5 days ago
$310
Roundtrip
found 5 days ago

Mon, Aug 17 - Wed, Aug 26
JFK
John F. Kennedy Intl.
MVY
Martha's Vineyard
$361 Roundtrip, found 2 days ago
$361
Roundtrip
found 2 days ago
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