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

Chapter House
Price was $1,158, price is now $974 per person
$974
per person
Sep 22 - Sep 26
found 22 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) 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

Inn on Main
Price was $1,259, price is now $1,042 per person
$1,042
per person
Oct 21 - Oct 25
found 16 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 16 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

Wequassett Resort and Golf Club
Price was $1,692, price is now $1,427 per person
$1,427
per person
Oct 21 - Oct 25
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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

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 17 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.

Morgan Hotel
Price was $2,147, price is now $1,966 per person
$1,966
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Vineyard Haven (MVY)
Stay at this hotel in Oak Bluffs. Enjoy free WiFi, concierge services, and cable TV channels. Popular attractions Inkwell Beach and Oak Bluffs Harbor are located nearby.

The Franklin Hotel Martha's Vineyard
Price was $1,600, price is now $1,483 per person
$1,483
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Vineyard Haven (MVY)
Stay at this hotel in Edgartown. Enjoy free WiFi, free parking, and cable TV channels. Popular attractions Inkwell Beach and Oak Bluffs Harbor are located nearby.

Margaritaville Resort Cape Cod
Price was $1,524, price is now $1,420 per person
$1,420
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Hyannis (HYA)
Book a stay at this spa resort in Hyannis. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the clean rooms in our reviews. Popular attractions Cape Codder Water Park and Cape Cod Melody Tent 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

Wed, Sep 9 - Wed, Sep 30
JFK
John F. Kennedy Intl.
MVY
Martha's Vineyard
$250 Roundtrip, found 6 days ago
$250
Roundtrip
found 6 days ago

Sat, Sep 26 - Wed, Oct 14
BOS
Logan Intl.
ACK
Nantucket Memorial
$270 Roundtrip, found 3 days ago
$270
Roundtrip
found 3 days ago

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
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