Cuttyhunk Fishing Vacations

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Flight and Fishing hotel deals in Cuttyhunk

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

Faraway Martha's Vineyard

CA $2,200
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
A few smaller items that made the stay slightly questionable, no elevator bags had to be carried. Not much to do about that in an historical building, but it's a note for guests. I would expect a notch better, especially when coming to bedding. The bed was comfortable, but I would expect down pillows and blanket at this price point. The record player was a lovely touch. Parking was challenging, but again, historical town we must make compromises. Wonderful shower towels, GREAT pool and hot tub area. The location of the hotel is / was supreme. Only coffee offered in the lobby, no inroom machine, and no option of a latte, or capp in the hotel or lobby, only in adjacent restaurant. (Loud bathroom fan, bug in room, a little mildew build up on the shower grout, definite degradation happening on plumbing fixtures. At this price point, should be better)

Reviewed on Sep 17, 2026

Harbor View Hotel

Harbor View Hotel

CA $2,545
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
We always enjoy our stays at the Harbor View. The rooms are terrific and beautifully appointed, and the staff is consistently helpful and friendly. The front veranda, with its sweeping views of Edgartown Lighthouse, the Atlantic Ocean, and Chappaquiddick, is truly delightful. The on-site Bettini Restaurant is another fabulous amenity—convenient, inviting, and absolutely delicious. You simply can’t go wrong booking a stay at the Harbor View!

Reviewed on Sep 16, 2026

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5* Fishing holidays in Cuttyhunk

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

Harbor View Hotel

CA $2,545
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
We always enjoy our stays at the Harbor View. The rooms are terrific and beautifully appointed, and the staff is consistently helpful and friendly. The front veranda, with its sweeping views of Edgartown Lighthouse, the Atlantic Ocean, and Chappaquiddick, is truly delightful. The on-site Bettini Restaurant is another fabulous amenity—convenient, inviting, and absolutely delicious. You simply can’t go wrong booking a stay at the Harbor View!

Reviewed on Sep 16, 2026

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3 Night Fishing holidays in Cuttyhunk

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

Faraway Martha's Vineyard

CA $1,905
per person
Dec 2 - Dec 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
A few smaller items that made the stay slightly questionable, no elevator bags had to be carried. Not much to do about that in an historical building, but it's a note for guests. I would expect a notch better, especially when coming to bedding. The bed was comfortable, but I would expect down pillows and blanket at this price point. The record player was a lovely touch. Parking was challenging, but again, historical town we must make compromises. Wonderful shower towels, GREAT pool and hot tub area. The location of the hotel is / was supreme. Only coffee offered in the lobby, no inroom machine, and no option of a latte, or capp in the hotel or lobby, only in adjacent restaurant. (Loud bathroom fan, bug in room, a little mildew build up on the shower grout, definite degradation happening on plumbing fixtures. At this price point, should be better)

Reviewed on Sep 17, 2026

Harbor View Hotel

Harbor View Hotel

CA $2,014
per person
Dec 2 - Dec 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
We always enjoy our stays at the Harbor View. The rooms are terrific and beautifully appointed, and the staff is consistently helpful and friendly. The front veranda, with its sweeping views of Edgartown Lighthouse, the Atlantic Ocean, and Chappaquiddick, is truly delightful. The on-site Bettini Restaurant is another fabulous amenity—convenient, inviting, and absolutely delicious. You simply can’t go wrong booking a stay at the Harbor View!

Reviewed on Sep 16, 2026

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See all available trips from Columbus to Cuttyhunk
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4 Night Fishing holidays in Cuttyhunk

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

Faraway Martha's Vineyard

CA $2,200
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
A few smaller items that made the stay slightly questionable, no elevator bags had to be carried. Not much to do about that in an historical building, but it's a note for guests. I would expect a notch better, especially when coming to bedding. The bed was comfortable, but I would expect down pillows and blanket at this price point. The record player was a lovely touch. Parking was challenging, but again, historical town we must make compromises. Wonderful shower towels, GREAT pool and hot tub area. The location of the hotel is / was supreme. Only coffee offered in the lobby, no inroom machine, and no option of a latte, or capp in the hotel or lobby, only in adjacent restaurant. (Loud bathroom fan, bug in room, a little mildew build up on the shower grout, definite degradation happening on plumbing fixtures. At this price point, should be better)

Reviewed on Sep 17, 2026

Harbor View Hotel

Harbor View Hotel

CA $2,545
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
We always enjoy our stays at the Harbor View. The rooms are terrific and beautifully appointed, and the staff is consistently helpful and friendly. The front veranda, with its sweeping views of Edgartown Lighthouse, the Atlantic Ocean, and Chappaquiddick, is truly delightful. The on-site Bettini Restaurant is another fabulous amenity—convenient, inviting, and absolutely delicious. You simply can’t go wrong booking a stay at the Harbor View!

Reviewed on Sep 16, 2026

The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

CA $2,263
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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

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