
Cuttyhunk Vacation Packages
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Top Cuttyhunk Vacation Deals
Price found within the past 48 hours. Click for updated prices.



Morgan Hotel
CA $1,730
per person
Sep 16 - Sep 20
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.6/10 Excellent! (243 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 on Aug 4, 2026

Faraway Martha's Vineyard
CA $3,168
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9/10 Wonderful! (1,004 reviews)
We came here on our anniversary and could not have picked a better place. The boutique-yet-full-service hotel is elegant and beautiful, with great taste everywhere and amazing ocean views. The heated (perfect temperature) pool and jacuzzi were a perfect spot to take a break at any time in the day, with relaxing and happy lounge music. Most importantly, the staff is highly well trained, educated, and devoted to service with a smile without the attitude sometimes found in premium hotels sometimes. Mattia (spelling?), Duna, Julian were amazing. Coffee in the room a great plus! Short walk from the ferry (3 minutes!) and in the center of the action makes this hard to beat. I would only add more obvious breakfast choices (most guests just go out to great options short walks away) to make this even more perfect. We will certainly be back.
Reviewed on Jul 28, 2026

The Christopher, The Edgartown Collection
CA $2,280
per person
Sep 6 - Sep 10
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9.8/10 Exceptional! (263 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 at 3 pm - we actually raced back to the hotel for these; they were so good! And the homemade breakfasts served each morning with delicious, strong coffee were a welcome way to start the day. I've already started planning a girls' trip to the island and The Christopher is where we'll stay!
Reviewed on Aug 3, 2026
Ready to book your vacation to Cuttyhunk?
Cuttyhunk Hotel Deals

Vineyard Harbor Motel - Private Beach
60 Beach Road Vineyard Haven MA
CA $376
CA $420 total
Sep 3 - Sep 4
includes taxes & fees

New Bedford Harbor Hotel
222 Union St New Bedford MA
Fully refundableReserve now, pay when you stay
CA $223
CA $249 total
Aug 30 - Aug 31
includes taxes & fees
8.2/10 Very good! (1,013 reviews)
"The hotel has a nice restaurant next to the lobby. The burger was delicious. One night, when the restaurant was closed, a very friendly young man at the front desk recommended that I go to National Club. It was a great find. It's a Mexican restaurant with a twist. Have the ceviche mixto. The helpfulness ..."
Reviewed on Aug 7, 2026

AutoCamp Cape Cod
836 Palmer Avenue Falmouth MA
CA $153
CA $231 total
Aug 30 - Aug 31
includes taxes & fees
9.4/10 Exceptional! (373 reviews)
"Everything was easy and we loved our stay! Definitely recommend it and we will come back again!"
Reviewed on Aug 7, 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 $1,617, 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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- 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
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- National Monument to the Forefathers
- Craigville Beach
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- Sandwich Glass Museum
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- Jenney Grist Mill
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







