Cuttyhunk Pet-friendly Vacations

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Flight and Pet-friendly hotel deals in Cuttyhunk

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

Faraway Martha's Vineyard

CA $4,201
per person
Sep 11 - Sep 15
found 1 day 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

Harbor View Hotel

Harbor View Hotel

CA $6,067
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
We had an amazing stay and we can not wait to be back.

Reviewed on Jul 31, 2026

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5* Pet-friendly holidays in Cuttyhunk

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

Harbor View Hotel

CA $6,067
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
We had an amazing stay and we can not wait to be back.

Reviewed on Jul 31, 2026

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3 Night Pet-friendly holidays in Cuttyhunk

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

Faraway Martha's Vineyard

CA $2,685
per person
Sep 17 - Sep 20
found 6 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

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4 Night Pet-friendly holidays in Cuttyhunk

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

Morgan Hotel

CA $2,988
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.6/10 Excellent! (243 reviews)
The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

CA $3,144
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9.2/10 Wonderful! (199 reviews)
Harbor View Hotel

Harbor View Hotel

CA $6,067
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
We had an amazing stay and we can not wait to be back.

Reviewed on Jul 31, 2026

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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.