
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.

Summercamp
CA $1,221
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Vineyard Haven (MVY)
9.4/10 Exceptional! (1,000 reviews)
The location across from the harbor is wonderful and the large porch with rockers and other furniture is great anytime of the day for just hanging our or people watching.....the best feature of the hotel in my opnion. As it is off a main street, however, it is noisy at times with traffic. It is a large property and I stayed in a room in one of the annex buildings--rooms are small for the high price, no closet just a pole over the dresser with hangers, room had a touch of that damp "beach" odor so some type of aroma enhancement would have made things a lot better. For the price, I also would have expected some higher end toiletries than the standard large receptacles in the shower...not sure what the product was, but this seems to be the way all hotels are going. Bed was extremely comfortable. Air coniditoner was noisy, but worked, Refrigerator in the room is a nice amenity but really small as it fits inside a cabinet and could hold limited items--it got cool, never really cold despite being on the highest setting. If you needed wine bottles chilled forget it. The staff, however, is very warm and welcoming and attentive to needs when asked for things. The lobby is spacious, nicely decorated and they have a large seating area for breakfast. Coffee was good and complimentary and breakfast items available for sale...a variety of yogurt and baked goods if you did not was to go out. If you have a car, I would recommend buying one of the limited spaces they offer.
Reviewed on Aug 28, 2026

Faraway Martha's Vineyard
CA $1,581
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Vineyard Haven (MVY)
9/10 Wonderful! (1,001 reviews)
I enjoyed my stay in the Chappy House – Room 409, a suite with its on entrance from the outside. It was very well appointed and similar to a spacious one bedroom apartment without the kitchen. Must be capable of maneuvering stone pathways and steps to access it. Very nice for a long-term stay. I’d be interested in purchasing one! (Luxury vinyl plank flooring needs repairing in one hallway spot — barely noticeable.) 🙂
Reviewed on Aug 20, 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 $166
CA $185 total
Sep 27 - Sep 28
includes taxes & fees

Vineyard Harbor Motel - Private Beach
60 Beach Road Vineyard Haven MA
CA $417
CA $466 total
Sep 17 - Sep 18
includes taxes & fees

AutoCamp Cape Cod
836 Palmer Avenue Falmouth MA
Fully refundableReserve now, pay when you stay
CA $151
CA $228 total
Sep 13 - Sep 14
includes taxes & fees
9.2/10 Wonderful! (385 reviews)
"On first perception, thought the airstream was a little small, but quickly fell in love with the surroundings and area. I advise to buy the marshmallows and wood from a super store (half the price), but our family ended up having an excellent time, and it ended up being the fave part of our trip ..."
Reviewed on Aug 29, 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 $1,221, 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
- Cottages in Martha's Vineyard
- The Charming Gem Near The Water!
- Lgbt Friendly Hotels in Fairhaven
- Condo Rentals in Martha's Vineyard
- Westport Hotels
- Cheap Hotels in New Bedford
- Houseboats in Westport
- Marriott Hotels & Resorts in Martha's Vineyard
- New Bedford Hotels
- Golf Hotels in Martha's Vineyard
- B&B in Martha's Vineyard
- South Dartmouth Hotels
- Oceanfront Hotels in New Bedford
- Pet-Friendly Hotels in Martha's Vineyard
- Beach Hotel Hotels in New Bedford
- Oceanfront Hotels in Martha's Vineyard
- Cabin Rentals in Martha's Vineyard
- Hotels near New Bedford Seastreak Ferry Terminal
- North Dartmouth Hotels
- All Inclusive Resorts and in Martha's Vineyard
- Houseboats in Dartmouth
- Houseboats in West Tisbury
- 5 Star Hotels in New Bedford
- Woods Hole Hotels
- Spacious Solar Powered Beach Vacation Home
- Adults Only Resorts & in Martha's Vineyard
- Peaceful Chilmark Farmhouse by Menemsha Beach
- Beach Hotel Hotels in Martha's Vineyard
- Motels in New Bedford
- Lgbt Friendly Hotels in Martha's Vineyard
- Adults Only Resorts & in New Bedford
- Shopping Hotels in Martha's Vineyard
- 3 Star Hotels in Martha's Vineyard
- Motels in Martha's Vineyard
- Seaport Resort & Marina
- Hilton Hotels in Martha's Vineyard
- 5 Star Hotels in Martha's Vineyard
- Falmouth Hotels
- Treehouse Lodge
- Fairhaven Hotels
- Luxury Hotels in Martha's Vineyard
- Spa Hotels in Martha's Vineyard
- 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.








