Great Island Vacations from ￥190,108

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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The Latest Great Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

Downtown Portland
￥190,108
per person
Nov 18 - Nov 22
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Portland (PWM)
9.2/10 Wonderful! (1,864 reviews)
Comfortable

Reviewed on Oct 13, 2026

White Barn Inn & Spa, Auberge Collection

White Barn Inn & Spa, Auberge Collection

￥339,153
per person
Nov 18 - Nov 22
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Portland (PWM)
9.6/10 Exceptional! (124 reviews)

Find the Best Great Island Vacation Packages

Stay near popular Great Island attractions

Bailey Island Bridge

9.2/10 (10 reviews)
Find out about the history of Bailey Island when you spend time at Bailey Island Bridge. Stroll along the seaside or seek out the hiking trails.
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Land's End Gift Shop

10.0/10 (1 review)
Enjoy an outing to Land's End Gift Shop during your stay in Bailey Island. While you're in the area, find time to visit its shops.
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beach near Merritt House Road

Why not spend a lazy afternoon at beach near Merritt House Road during your trip to Orrs Island? Discover the mountain views while you're in the area.
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beach near Channel View Lane

Why not spend a lazy afternoon at beach near Channel View Lane during your trip to Bailey Island? Make time to visit the shops and monuments while you're in the area.
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Cobwork Bridge

10.0/10 (1 review)
You can find out about the history of Bailey Island when you stop by Cobwork Bridge. Stroll along the seaside or seek out the hiking trails.
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beach near Harpswell Islands Road

Why not spend a lazy afternoon at beach near Harpswell Islands Road during your trip to Orrs Island? Discover the mountain views while you're in the area.
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Frequently asked questions

How much does a Great Island vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Great Island from just ￥190,108. And the more you bundle, the more you save. The getaway of your dreams has never been more affordable.
How do I get a cheap travel package to Great Island?
One of the easiest ways to save dollars (and time) is to combine your bookings with Expedia. Flights, hotels, activities and rental cars — we've got it all. Pick a combination that suits you and see your savings pile up. Of course, a package deal is never one-size-fits-all. That's why we offer over 550 airlines and 1,000,000 properties globally, which lets you customize your Great Island vacation.
What are the top hotels in Great Island?
For properties in West Harpswell with cozy beds and friendly service, you can't top Cozy Cottage and Lofty Cottage. If you plan to visit Cundys Harbor as well, you'll get a good night's sleep at 1 Room Luxury Ocean Front Studio Cottage or Beaches, Boating, Cool Ocean Breezes.
How far in advance should I book my Great Island vacation?
Reserving your tickets early with Expedia means one less thing to worry about. Most carriers display prices up to 12 months prior to take off. This is typically the cheapest time to book. If circumstances have left you booking late, last-minute deals to Great Island occasionally appear just weeks before departure.
What does an Expedia Great Island travel package include?
Hotels, flights and rental cars — we've got them covered. With Expedia, you can shape your Great Island package the way you like it. All you have to do is figure out just what you need. Once you've made your booking, you can add on fun things like activities and experiences. The more you bundle, the bigger your savings!
What should I know before booking a Great Island travel package?
When you book your flights, hotels and car rentals together, you'll score terrific discounts. Whether you're planning a wilderness getaway in a cabin or prefer to stay in a luxurious city hotel, Expedia can make it happen for less.
Can I choose my airline with a Great Island Expedia vacation package?
Yes, and with over 550 airlines to pick from globally, you've got lots of choice. Take a look at the available options and see which airline best fits your needs and budget.
If I'm not able to travel, can I cancel my Great Island vacation package?
We understand — life can throw you the odd curveball. If you've locked in a Great Island vacation package and need to amend or cancel it, we're here to help. We suggest checking out our Customer Service Portal first for information. But in general, if you've taken out your package in the last 24 hours, you may be able to cancel or amend your itinerary at no cost. If it's been more than 24 hours, your airline, hotel or car rental company may charge a fee.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.