Cuttyhunk Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Ready to book your vacation to Cuttyhunk?

 

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Cuttyhunk Hotel Deals

New Bedford Harbor Hotel

New Bedford Harbor Hotel

3 out of 5
222 Union St New Bedford MA
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Nov 23 to Nov 24
CA $194
CA $217 total
Nov 23 - Nov 24
includes taxes & fees
8.2/10 Very good! (1,005 reviews)
"Bien situer"

Reviewed on Oct 30, 2026

New Bedford Harbor Hotel
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
60 Beach Road Vineyard Haven MA
The price is CA $265 per night from Nov 11 to Nov 12
CA $265
CA $296 total
Nov 11 - Nov 12
includes taxes & fees
9/10 Wonderful! (837 reviews)
"The room was freezing and there was no heater. The lights didn't work. The man at the front desk was not helpful and was never there. If you needed help, it said to call a number but the mail box was full and could not receive messages. It was a terrible experience. Don't stay here"

Reviewed on Oct 27, 2026

Vineyard Harbor Motel - Private Beach
Inn on the Square

Inn on the Square

3.5 out of 5
40 North Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Nov 24 to Nov 25
CA $190
CA $253 total
Nov 24 - Nov 25
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Property a little tired. Room had a v noisy refrigerator . Staff wonderful."

Reviewed on Oct 29, 2026

Inn on the Square
See all 1,226 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.
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Frequently asked questions

How much does a Cuttyhunk vacation package cost?
The cheapest Cuttyhunk package is , 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.

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