Cuttyhunk Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Cuttyhunk Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Harbor View Hotel
CA $2,438
per person
Dec 28 - Dec 31
found 4 hours ago
Roundtrip flight included
Montreal (YUL) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
Beautiful Hotel and Venue with impeccable amenities. Beautiful water views and outstanding and friendly Staff. Disappointed we were not able to stay longer. Will definitely plan another trip in the near future!
Reviewed on Oct 10, 2026
Vineyard Harbor Motel - Private Beach
CA $2,184
per person
Dec 28 - Dec 31
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to Vineyard Haven (MVY)
9/10 Wonderful! (812 reviews)
Went to check in and the code given to me did not work. Called the property manager and no response for 3 straight days.
Reviewed on Oct 14, 2026
Ready to book your vacation to Cuttyhunk?
Cuttyhunk Hotel Deals
New Bedford Harbor Hotel
222 Union St New Bedford MA
Fully refundableReserve now, pay when you stay
CA $180
CA $201 total
Oct 15 - Oct 16
includes taxes & fees
8.2/10 Very good! (1,000 reviews)
"Great place to stay if you’re in town"
Reviewed on Oct 13, 2026
Inn on the Square
40 North Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
CA $171
CA $231 total
Oct 25 - Oct 26
includes taxes & fees
Vineyard Harbor Motel - Private Beach
60 Beach Road Vineyard Haven MA
CA $248
CA $277 total
Oct 22 - Oct 23
includes taxes & fees
9/10 Wonderful! (825 reviews)
"Went to check in and the code given to me did not work. Called the property manager and no response for 3 straight days."
Reviewed on Oct 14, 2026
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 vacation package cost?
The cheapest Cuttyhunk package is CA $2,139, 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.
Explore a world of travel with Expedia
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- Adults Only Resorts & in Martha's Vineyard
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- Visit Woods Hole
- Visit Falmouth
- John F. Kennedy Memorial
- Keyes Beach
- Lizzie Borden Bed & Breakfast
- Mayflower II
- John F. Kennedy Hyannis Museum
- Seagull Beach
- Visit Martha's Vineyard
- Old Silver Beach
- Plymouth Rock
- Sandy Neck Beach
- Cisco Beach
- Plymouth Vacations
- Burial Hill
- Surf Drive Beach
- Visit Nantucket Island
- Menauhant Beach
- West Dennis Beach
- Kalmus Beach
- Nantucket Vacations
- Halifax Vacations
- National Monument to the Forefathers
- Craigville Beach
- Whydah Pirate Museum
- Sandwich Glass Museum
- Falmouth Vacations
- New Bedford Vacations
- Edaville
- South Cape Beach State Park
- Jenney Grist Mill
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
