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

Top Cuttyhunk Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
Price was CA $1,356, price is now CA $1,098 per person
CA $1,098
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Vineyard Haven (MVY)
9/10 Wonderful! (659 reviews)
Was a decent hotel. Nothing incredible but pretty clean for what it is. Staff was great. Beach was closed due bacteria from rain. Area near hotel needs improvements.

Reviewed on Jul 12, 2026

The Sydney, The Edgartown Collection

The Sydney, The Edgartown Collection

3.5 out of 5
Price was CA $2,973, price is now CA $2,420 per person
CA $2,420
per person
Aug 23 - Aug 27
found 14 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Vineyard Haven (MVY)
9.4/10 Exceptional! (193 reviews)
Great place to stay and staff are friendly and helpful. Had an issue with A/C in the room but staff did try to resolve the issue as quickly as possible. Would definitely recommend

Reviewed on Jul 5, 2026

The Richard, The Edgartown Collection

The Richard, The Edgartown Collection

3.5 out of 5
Price was CA $2,335, price is now CA $2,027 per person
CA $2,027
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Vineyard Haven (MVY)
9.6/10 Exceptional! (178 reviews)
When checking in, my daughter & 2 young grandchildren, I was told $300!!!! GREAT PRICE, right??? I just got billed $477+!!!!! WHY?

Reviewed on Jul 12, 2026

The Attleboro House

The Attleboro House

2.5 out of 5
Price was CA $1,456, price is now CA $1,280 per person
CA $1,280
per person
Aug 23 - Aug 27
found 14 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Vineyard Haven (MVY)
9.8/10 Exceptional! (98 reviews)
Easy check in, nobody bothers you and everything is clean! Will be going again

Reviewed on Jul 9, 2026

Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

3 out of 5
Price was CA $1,930, price is now CA $1,740 per person
CA $1,740
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Vineyard Haven (MVY)
8.4/10 Very good! (616 reviews)
Really good

Reviewed on Jul 10, 2026

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Cuttyhunk Hotel Deals

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
60 Beach Road Vineyard Haven MA
9/10 Wonderful! (675 reviews)
"Was a decent hotel. Nothing incredible but pretty clean for what it is. Staff was great. Beach was closed due bacteria from rain. Area near hotel needs improvements."

Reviewed on Jul 12, 2026

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Vineyard Harbor Motel - Private Beach
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 $191 per night from Jul 14 to Jul 15
CA $191
CA $214 total
Jul 14 - Jul 15
includes taxes & fees
8.2/10 Very good! (1,010 reviews)
"Clean room, pleasant staff, beautiful hotel"

Reviewed on Jul 12, 2026

New Bedford Harbor Hotel
AutoCamp Cape Cod

AutoCamp Cape Cod

4 out of 5
836 Palmer Avenue Falmouth MA
The price is CA $381 per night from Jul 20 to Jul 21
CA $381
CA $492 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (361 reviews)
"Great place to stay. Helpful staff"

Reviewed on Jul 7, 2026

AutoCamp Cape Cod
See all 1,211 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 CA $1,098, 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.