Cuttyhunk Luxury Vacations 2026

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Top Luxury vacation packages in Cuttyhunk

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

Faraway Martha's Vineyard

$1,681

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) 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

$1,742

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) 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* Luxury vacations in Cuttyhunk

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

Harbor View Hotel

$1,742

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) 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 Luxury vacations in Cuttyhunk

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

Faraway Martha's Vineyard

$1,681

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Vineyard Haven (MVY)

9/10 Wonderful! (1,000 reviews)

Reviewed on Aug 11, 2026

Harbor View Hotel

$1,742

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) 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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4 Night Luxury vacations in Cuttyhunk

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

Morgan Hotel

$1,396

per person

Sep 25 - Sep 29

found 1 day ago

Roundtrip flight included

Washington (DCA) to Vineyard Haven (MVY)

8.6/10 Excellent! (248 reviews)

The Christopher, The Edgartown Collection

Save 100% on your flight

$1,706

per person

Sep 14 - Sep 18

found 1 day ago

Roundtrip flight included

New York (NYC) to Vineyard Haven (MVY)

9.8/10 Exceptional! (268 reviews)

The Christopher is officially my new favorite hotel. Bailey greeted us when we arrived and was the primary person we saw during our stay. She was lovely and so helpful. I could have fainted when she offered to have our super heavy luggage taken up 3 flights of stairs for us! We were upgraded free of charge to a larger room that had its own private deck. The room was beautiful - gorgeous furnishings and so clean and comfortable. There are homemade, sinfully delicious chocolate chip cookies served at 3 pm - we actually raced back to the hotel for these; they were so good! And the homemade breakfasts served each morning with delicious, strong coffee were a welcome way to start the day. I've already started planning a girls' trip to the island and The Christopher is where we'll stay!

Reviewed on Aug 3, 2026

The Richard, The Edgartown Collection

$2,004

per person

Sep 25 - Sep 29

found 1 day ago

Roundtrip flight included

Washington (DCA) to Vineyard Haven (MVY)

9.6/10 Exceptional! (193 reviews)

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What can I expect from a luxury Cuttyhunk vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Cuttyhunk vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Cuttyhunk?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Cuttyhunk luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $1,396. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Cuttyhunk?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Cuttyhunk with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Cuttyhunk?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Cuttyhunk with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Cuttyhunk with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.