Chappaquiddick Island Honeymoon Vacations

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Flight and Honeymoon hotel deals in Chappaquiddick Island

Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

CA $753
per person
Sep 19 - Sep 21
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Hyannis (HYA)
8.6/10 Excellent! (664 reviews)
Faraway Martha's Vineyard

Faraway Martha's Vineyard

CA $1,267
per person
Oct 26 - Oct 30
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
We LOVED our stay at Faraway - the pool was amazing, staff was super helpful. They had a very convenient messaging system for requests. The staff recommended the Pelican Club for dinner, which is basically right on-site, but we tried to get in multiple times and there was always a wait! The food at their snack bar was really good for lunch. The location was incredible - it was our first time in Martha's Vineyard and we feel we got so spoiled!!

Reviewed on Aug 11, 2026

Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

CA $2,576
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hyannis (HYA)
9.4/10 Exceptional! (265 reviews)
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

Harbor View Hotel

Harbor View Hotel

CA $1,389
per person
Oct 26 - Oct 30
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
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5* Honeymoon holidays in Chappaquiddick Island

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

Harbor View Hotel

CA $1,389
per person
Oct 26 - Oct 30
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

CA $2,576
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hyannis (HYA)
9.4/10 Exceptional! (265 reviews)
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

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4 Night Honeymoon holidays in Chappaquiddick Island

Price found within the past 48 hours. Click for updated prices.
Faraway Martha's Vineyard

Faraway Martha's Vineyard

CA $1,267
per person
Oct 26 - Oct 30
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
We LOVED our stay at Faraway - the pool was amazing, staff was super helpful. They had a very convenient messaging system for requests. The staff recommended the Pelican Club for dinner, which is basically right on-site, but we tried to get in multiple times and there was always a wait! The food at their snack bar was really good for lunch. The location was incredible - it was our first time in Martha's Vineyard and we feel we got so spoiled!!

Reviewed on Aug 11, 2026

Inn on Main

Inn on Main

CA $1,602
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hyannis (HYA)
10/10 Exceptional! (78 reviews)
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

Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

CA $1,421
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hyannis (HYA)
9.4/10 Exceptional! (1,006 reviews)
Great stay with friendly staff. We would not hesitate to return!

Reviewed on Aug 16, 2026

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Things to do

Martha's Vineyard Self-Driving Audio Tour

Martha's Vineyard: Self-Guided Driving Audio Tour

CA $21
per traveller
Martha's Vineyard: Self-Guided Driving Audio Tour
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

CA $70
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

CA $71
per traveller
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Chappaquiddick Island

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.