Cuttyhunk Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Cuttyhunk Vacation Deals

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

Vineyard Harbor Motel - Private Beach

2.5 out of 5
per person
Sep 26 - Sep 30
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9/10 Wonderful! (484 reviews)
Unexpected gem. On the waterfront, bus line, and shopping area.

Reviewed on Aug. 11, 2025

The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

2 out of 5
per person
Sep 26 - Sep 30
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9.2/10 Wonderful! (149 reviews)
We thoroughly enjoyed or stay here.

Reviewed on Aug. 10, 2025

Morgan Hotel

Morgan Hotel

2.5 out of 5
per person
Sep 26 - Sep 30
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.4/10 Very Good! (164 reviews)
AC is a bit noisy in this tiny room, but location is great.

Reviewed on Aug. 11, 2025

The Sydney, The Edgartown Collection

The Sydney, The Edgartown Collection

3.5 out of 5
per person
Sep 26 - Sep 30
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9.4/10 Exceptional! (160 reviews)
Fresh breakfast from local farm was excellent. Close to many shops and restaurants. Would stay here again.

Reviewed on Jul. 13, 2025

The Richard, The Edgartown Collection

The Richard, The Edgartown Collection

3.5 out of 5
per person
Sep 19 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9.6/10 Exceptional! (155 reviews)
The rooms we stayed in was small but expected for a boutique . The 3 girls that attended the desk were fabulous. Beds were comfortable. It was great for a short stay.

Reviewed on Jul. 31, 2025

Ready to book your vacation to Cuttyhunk?

 

Choose your dates

Cuttyhunk Hotel Deals

Atlantic Beach Hotel Newport

Atlantic Beach Hotel Newport

3.5 out of 5
28 Aquidneck Ave, Middletown, RI
The price is CA $222 per night from Sep 2 to Sep 3
CA $222
CA $266 total
Sep 2 - Sep 3
includes taxes & fees
8.4/10 Very Good! (1,237 reviews)
"great location fright off beach"

Reviewed on Aug. 8, 2025

Atlantic Beach Hotel Newport
Wyndham Newport Hotel

Wyndham Newport Hotel

4 out of 5
240 Aquidneck Avenue, Middletown, RI
The price is CA $284 per night from Sep 1 to Sep 2
CA $284
CA $352 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (1,122 reviews)
"We loved it here. Will definitely return!"

Reviewed on Aug. 11, 2025

Wyndham Newport Hotel
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street, Route 28, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Sep 1 to Sep 2
CA $187
CA $235 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,009 reviews)
"Great & friendly staff. Nice clean room. Exterior ground could have been in better conditions. Outdoor furniture & exterior lounging area not in good condition."

Reviewed on Aug. 11, 2025

Falmouth Inn
See all 1,486 properties in Cuttyhunk
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Cuttyhunk vacation package cost?
The cheapest Cuttyhunk package is CA $1,670, so your dream vacation can become a reality — without a hefty price tag. Bundle flights, hotels and car rentals to tailor a package suited to your traveling style.
How do I get a cheap travel package to Cuttyhunk?
One of the simplest ways to save money (and time) is to bundle your bookings with Expedia. Hotels, flights, activities and rental cars — we've got them all covered. Choose a combination that best suits you and watch your savings grow. Of course, a travel package is never a one-size-fits-all. That's why Expedia offers over 550 air carriers and 1,000,000 hotels around the globe, which lets you customize your Cuttyhunk adventure.
Where should I stay in Cuttyhunk?
A getaway to Cuttyhunk wouldn't be complete without checking out Barges Beach. Why not stay near this interesting tourist attraction?
How far in advance should I book my Cuttyhunk vacation?
Smart travelers often reserve their seats as early as possible. You can generally start comparing international fares on Expedia up to a year before your flight. If you're purchasing your ticket at the last minute, there's no need to worry. Discounted prices occasionally occur just weeks before departure.
What does an Expedia Cuttyhunk travel package include?
Hotels, flights and rental cars, or any combination of them — you decide! Whether you're headed to Cuttyhunk with the kids or traveling solo, there's a bundle to match every budget and style. Once you've made your booking, why not add on a few tours as well?
What should I know before booking a Cuttyhunk travel package?
You'll enjoy terrific savings when you combine your flights, hotels and rental cars into a travel package. Not only that, booking everything in one spot simply makes planning easier. So why waste your money or time? Whether you're organizing a ritzy city getaway or a budget family adventure, take a look at our package deals today.
Can I choose my airline with a Cuttyhunk Expedia vacation package?
You can, and with over 550 airlines to select from around the world, it's all about choice. Have a look through the available options and see which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Cuttyhunk vacation package?
Yes, it's possible to cancel your Cuttyhunk booking if your travel plans have changed. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. It may be possible to cancel or change for free if you booked in the last 24 hours. Visit our Customer Service Portal for more information.

Other 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.