Cuttyhunk Romantic Vacations

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Top Romantic vacation packages in Cuttyhunk

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

Harbor View Hotel

$819
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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

Faraway Martha's Vineyard

Faraway Martha's Vineyard

$1,451
per person
Dec 11 - Dec 15
found 18 hours ago
Roundtrip flight included
New York (NYC) 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

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5* Romantic vacations in Cuttyhunk

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

Harbor View Hotel

$819
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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 Romantic vacations in Cuttyhunk

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

Faraway Martha's Vineyard

$1,124
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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

$1,207
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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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4 Night Romantic vacations in Cuttyhunk

Price found within the past 48 hours. Click for updated prices.
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

$554
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Vineyard Haven (MVY)
9/10 Wonderful! (773 reviews)
We spent one night at this motel. So, we didn’t get to enjoy all of the amenities. It was clean and comfortable. There was a market and restaurant directly across the street. The location was great. The staff was very courteous and helpful.

Reviewed on Sep 21, 2026

Faraway Martha's Vineyard

Faraway Martha's Vineyard

$1,451
per person
Dec 11 - Dec 15
found 18 hours ago
Roundtrip flight included
New York (NYC) 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

$819
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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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How to find a romantic Cuttyhunk vacation

How can I find the best Cuttyhunk vacation packages for couples?

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Cuttyhunk romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.

How can I plan a great romantic trip to Cuttyhunk?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Cuttyhunk?

Put a price on love with stunning deals for duos starting at just $554. Prices and availability are subject to change. Additional terms may apply.

Can I book Cuttyhunk spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

How can I book romantic weekend getaway packages in Cuttyhunk?

To book a loved-up break in Cuttyhunk, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

Can I book a romantic trip to Cuttyhunk with free cancellation and/or flexible dates?

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

Why should I book my Cuttyhunk romantic holiday with Expedia?

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?

More vacations you might like

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