Cuttyhunk Vacation Packages 2026 from $784

Cuttyhunk flight + hotel vacation packages

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

Vineyard Harbor Motel - Private Beach

$784

per person

Oct 22 - Oct 27

found 17 hours ago

Roundtrip non-stop flight included

Charlotte (CLT) to Vineyard Haven (MVY)

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a picnic area, and luggage storage are also on offer.

The Christopher, The Edgartown Collection

$1,480

per person

Oct 16 - Oct 18

found 23 hours ago

Roundtrip flight included

New York (NYC) to Vineyard Haven (MVY)

Free WiFi in public areas, a terrace, and a garden are available at this bed & breakfast. Enjoy the free self-serve breakfast each morning. A communal living room and express check-out are also provided.

Harbor View Hotel

$1,419

per person

Oct 16 - Oct 18

found 23 hours ago

Roundtrip flight included

New York (NYC) to Vineyard Haven (MVY)

This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and free valet parking. Enjoy the seasonal outdoor pool and perks like free self parking.

The Island Inn on Martha's Vineyard

$1,314

per person

Oct 16 - Oct 18

found 23 hours ago

Roundtrip flight included

New York (NYC) to Vineyard Haven (MVY)

This resort's 3 outdoor tennis courts and seasonal outdoor pool are among the featured amenities. There's no skimping on freebies - guests receive free WiFi, free self parking, and a free beach shuttle. A garden, a picnic area, and laundry facilities are also on offer.

Faraway Martha's Vineyard

$1,639

per person

Oct 16 - Oct 18

found 23 hours ago

Roundtrip flight included

New York (NYC) to Vineyard Haven (MVY)

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.

Top Cuttyhunk hotels deals

New Bedford Harbor Hotel

222 Union St New Bedford MA

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$133 total

Sep 28 - Sep 29

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. Luggage storage is provided and the front desk is staffed around-the-clock.

Parking included

Free WiFi

Inn on the Square

40 North Main Street Falmouth MA

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$174 total

Oct 14 - Oct 15

Total with taxes and fees

A restaurant and an indoor pool are featured at this hotel. WiFi in public areas is free. A garden is provided and the front desk is staffed around-the-clock.

Pool

Free WiFi

AutoCamp Cape Cod

836 Palmer Avenue Falmouth MA

$122 nightly

$140 total

Oct 4 - Oct 5

Total with taxes and fees

This holiday park doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A coffee shop, a terrace, and a garden are also on offer.

Pet friendly

Parking included

Vineyard Harbor Motel - Private Beach

60 Beach Road Vineyard Haven MA

$178 nightly

$199 total

Oct 1 - Oct 2

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a picnic area, and luggage storage are also on offer.

On private beach

Parking included

Whaler Inn and Suites

500 Hathaway Rd New Bedford MA

$111 nightly

$124 total

Sep 17 - Sep 18

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. There's no skimping on freebies - guests receive free breakfast, free WiFi, and free self parking. A convenience store is provided and the front desk is staffed around-the-clock.

Pool

Breakfast included

Seaport Resort & Marina

110 Middle St Fairhaven MA

$116 nightly

$130 total

Sep 29 - Sep 30

Total with taxes and fees

A marina and an indoor pool are featured at this smoke-free hotel. Business travelers can take advantage of the business center. Free self parking, express check-out, and a computer station are also offered.

Pool

Pet friendly

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much are vacation packages to Cuttyhunk?

Travelocity offers hotel and flight vacation packages starting from just $784. With these kinds of deals, you'll be exploring all of Cuttyhunk in a flash.

Where can I get the best vacation package deals for Cuttyhunk?

It's hard to beat Travelocity when it comes to putting together your Cuttyhunk package deal. There are as many as 400 airlines and 1,000,000 properties worldwide to select from. Book your vacation now and get ready to cross another place off your list.

Why should I purchase my Cuttyhunk vacation bundle via Travelocity?

Whether you're planning an epic vacation or a last-minute trip, we have lots of alluring destinations to choose from at an affordable rate. On top of that, we provide customer support 24/7, top-notch service and a Price Match Guarantee. Save yourself the effort and time and lock in your dream vacation today.

Can I save on my Cuttyhunk car rental if I bundle it with a hotel or flight?

With a Cuttyhunk vacation package, you can bundle your hotel, flight and car bookings and save loads. If you want to explore the best of this wonderful destination, why not make tracks to Fenway Park? This famous sight is 65 mi from Cuttyhunk. With a rental car, you'll be there in the blink of an eye.

Which airport is best for Cuttyhunk?

It's very likely you'll touch down at T.F. Green Airport (PVD), which is 35 mi northwest of inner Cuttyhunk. Martha's Vineyard Airport (MVY) (17 mi away from central Cuttyhunk) and Nantucket Memorial Airport (ACK) (45 mi away from central Cuttyhunk) are your other options.

What is there to do in Cuttyhunk?

Barges Beach should be toward the top of your must-see list. Once you've crossed off this top attraction, simply stroll the streets of Cuttyhunk and get a feel for what makes this cool destination tick.

Where should I stay when visiting Cuttyhunk?

The Scenic, hip and remote compound on Cuttyhunk Island is recommended by many travelers. Book as soon as possible before it's too late.