Great Island Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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 hotels in Great Island

Oceanfront Studio w/ Private Dock in Harpswell!

Oceanfront Studio w/ Private Dock in Harpswell!

Harpswell ME
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Oceanfront Studio w/ Private Dock in Harpswell!
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME
Fully refundable
S$154
8 Sept - 9 Sept
includes taxes & fees
8.2/10 Very good! (1,631 reviews)
"Good enough for a one night stay over if flying in/out. Shuttle service was superb. Front desk staff was helpful. Not a five star hotel and the conference area was a bit rowdy with a wedding. However, our room was far away and we were not disturbed."

Reviewed on 27 Aug, 2026

Clarion Hotel Portland Airport ME
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
S$154
28 Sept - 29 Sept
includes taxes & fees
Fireside Inn & Suites Portland
See all 2,290 properties in Great Island
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.
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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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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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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.
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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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beach near Mackerel Cove Lot

Why not spend a lazy afternoon at beach near Mackerel Cove Lot during your trip to Bailey Island? Make time to visit the shops and monuments while you're in the area.
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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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.