Cuttyhunk Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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

Top hotels in Cuttyhunk

New Bedford Harbor Hotel

New Bedford Harbor Hotel

222 Union St New Bedford MA
Fully refundableReserve now, pay when you stay
S$227
30 Aug - 31 Aug
includes taxes & fees
New Bedford Harbor Hotel
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

60 Beach Road Vineyard Haven MA
S$385
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (730 reviews)
"Everything is great about this property. The staff is really nice. Also, there are many places to sit outside if you don’t feel like sitting on the beach. The room was very clean. It is also very close to lots of places to eat."

Reviewed on 10 Aug, 2026

Vineyard Harbor Motel - Private Beach
AutoCamp Cape Cod

AutoCamp Cape Cod

836 Palmer Avenue Falmouth MA
S$211
30 Aug - 31 Aug
includes taxes & fees
9.4/10 Exceptional! (374 reviews)
"Overall our stay was really great and I would come back again. The staff was great and helpful! The bathroom is really the only place that I didn’t ’like’. We stayed in an airstream and it just could have been a little cleaner. I understand we are ‘camping’ but the windows in the bathroom were pretty ..."

Reviewed on 8 Aug, 2026

AutoCamp Cape Cod
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.

Frequently asked questions

How much does a Cuttyhunk holiday package cost?
The cheapest Cuttyhunk package is , so your dream holiday can become a reality — without a hefty price tag. Bundle flights, hotels and car rentals to tailor a package suited to your travelling 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 holiday?
Smart travellers 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 travelling 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 organising 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 holiday 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 holiday 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.