Cuttyhunk Vacation Packages
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The Latest Cuttyhunk Vacation Packages
- The Island Inn on Martha's Vineyard
Oct 2 - Oct 5The Island Inn on Martha's Vineyard + Flight
Oak Bluffs3 nights2.5 star property8.4/10 - Very good (43 reviews)"Proximity to major attractions in area and yet far enough away from all the hustle and bustle."Reviewed August 5, 2026Roundtrip • Halifax (YHZ) - Vineyard Haven (MVY)YHZ - BOS • 1 stop BOS - YHZ • NonstopCA $1,442CA $1,264found 1 day agoper traveller - Vineyard Harbor Motel - Private Beach
Sept 16 - Sept 20Vineyard Harbor Motel - Private Beach + Flight
Vineyard Haven4 nights2.5 star property9.0/10 - Wonderful (721 reviews)Roundtrip • Toronto (YTO) - Vineyard Haven (MVY)YTZ - BOS • Nonstop BOS - YTZ • NonstopCA $2,078CA $1,618found 6 hours agoper traveller - The Christopher, The Edgartown Collection
Sept 6 - Sept 10The Christopher, The Edgartown Collection + Flight
Edgartown4 nights3.0 star property9.8/10 - Exceptional (268 reviews)"The Christopher is officially my new favorite hotel. Bailey greeted us when we arrived and was the primary person we saw during our stay. She was lovely and so helpful. I could have fainted when she offered to have our super heavy luggage taken up 3 flights of stairs for us! We were upgraded free of charge to a larger room that had its own private deck. The room was beautiful - gorgeous furnishings and so clean and comfortable. There are homemade, sinfully delicious chocolate chip cookies served..."Reviewed August 3, 2026Roundtrip • Toronto (YTO) - Vineyard Haven (MVY)YTZ - BOS • Nonstop BOS - YTZ • NonstopCA $2,748CA $2,280found 6 hours agoper traveller - Morgan Hotel
Oct 2 - Oct 5Morgan Hotel + Flight
Oak Bluffs3 nights2.5 star property8.6/10 - Excellent (248 reviews)"The first room we were in was right next to the street and lobby and was quite loud. They were very accommodating and moved us upstairs to a quiet room. Overall a great hotel with great service."Reviewed August 4, 2026Roundtrip • Halifax (YHZ) - Vineyard Haven (MVY)YHZ - BOS • 1 stop BOS - YHZ • NonstopCA $1,483CA $1,280found 1 day agoper traveller - The Franklin Hotel Martha's Vineyard
Oct 2 - Oct 5The Franklin Hotel Martha's Vineyard + Flight
Edgartown3 nights2.0 star property9.2/10 - Wonderful (200 reviews)Roundtrip • Halifax (YHZ) - Vineyard Haven (MVY)YHZ - BOS • 1 stop BOS - YHZ • NonstopCA $1,751CA $1,528found 1 day agoper traveller
Cuttyhunk Hotel Deals
"Everything was easy and we loved our stay! Definitely recommend it and we will come back again!"
"Nice place to stay! The outside may look like it needs renovation (probably forthcoming), but our room was newly renovated and very nice. They even thoughtfully included built-in charging stations on both nightstands. The rate (through Expedia) was very reasonable, compared to other properties in the area. The breakfast included coffee, several juices, two different cereals, oatmeal, muffins, granola bars, yogurt, and a Belgium waffle machine. Didn't use the indoor pool, but it looked...
Best Western Dartmouth-New Bedford
Best Western Dartmouth-New Bedford"The hotel stayed was marred by a fire on our first night. The room was not accessible for 3-4 hours while the fire was put out. We stayed the second night only to continue to smell smoke even though hydroxyl generators were running during the stay. Both management and corporate customer service refused any refund, discount or voucher."
Hampton Inn by Hilton New Bedford/Fairhaven
Hampton Inn by Hilton New Bedford/Fairhaven
Baymont by Wyndham North Dartmouth / Fall River
Baymont by Wyndham North Dartmouth / Fall River"great stay"
Fairfield Inn & Suites by Marriott New Bedford
Fairfield Inn & Suites by Marriott New BedfordFrequently Asked Questions
How much does a Cuttyhunk vacation package cost?
The cheapest Cuttyhunk package is CA $1,264, 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.