Great Island Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 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
Great Island Holiday
Our pick of the best Great Island Hotel Deals
Oceanfront Studio w/ Private Dock in Harpswell!
Harpswell ME
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
NZ$140
10 Sept - 11 Sept
includes taxes & fees
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
NZ$215
10 Sept - 11 Sept
includes taxes & fees
8.4/10 Very good! (3,005 reviews)
"Staff was very friendly and courteous."
Reviewed on 2 Sept 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.
Stay near popular Great Island attractions
Bailey Island Bridge
9.2/10 (10 reviews)
Find out about the history of Bailey Island with a stop at Bailey Island Bridge. Stroll along the seaside or seek out the hiking trails.
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.
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.
beach near Bailey Island
Why not spend a lazy afternoon at beach near Bailey Island during your trip to Bailey Island? Make time to visit the shops and monuments while you're in the area.
Cobwork Bridge
10.0/10 (1 review)
You can find out about the history of Bailey Island with a visit to Cobwork Bridge. Stroll along the seaside or seek out the hiking trails.
beach near Harpswell Harbor
Why not spend a lazy afternoon at beach near Harpswell Harbor during your trip to Harpswell? Discover the area's sunsets and mountain views.
Frequently asked questions
How much does a Great Island holiday package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Great Island from just . 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 holiday.
What are the top hotels in Great Island?
For properties in West Harpswell with cosy beds and friendly service, you can't top Cosy Cottage and Lofty Cottage. If you plan to visit Cundys Harbour 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 holiday?
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 holiday 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 holiday package?
We understand — life can throw you the odd curveball. If you've locked in a Great Island holiday 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
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- Fort Williams Park
- Port City Music Hall
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- Cathedral Church of Saint Luke
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- Scuba Diving Holiday Packages Casco Bay Islands
- Visit Casco Bay Islands
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- Visit Cundys Harbor
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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.
