Bailey Island Holidays

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Your Bailey Island Holiday

With one of our holiday packages to Bailey Island, you'll have limitless opportunities for adventure and relaxation. There's a lot to look forward to, including its coastal scenery and spectacular views. If your trip to Bailey Island includes a little sightseeing, drop by well-known attractions like Bailey Island Bridge, Lands End Gift Shop and Eagle Island. Your Bailey Island holiday is clicks away. Explore hotels, airfares and more on Expedia for an adventure that's tailored just for you.

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Bailey Island Holiday

Bailey Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Max Temp Winter
-1.11ºC
Max Temp Summer
21ºC
Top Sights
Sand Beach, Thomas Point Beach and Wolfes Neck Woods State Park

Our pick of the best Bailey Island Hotel Deals

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Bailey Island
9.8/10 Exceptional! (74 reviews)
Paradise!
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time."

Reviewed on 17 Oct. 2024

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
La Quinta Inn & Suites by Wyndham Portland
La Quinta Inn & Suites by Wyndham Portland
2.5 out of 5
340 Park Ave, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$141 per night from 27 Nov to 28 Nov
AU$141
includes taxes & fees
27 Nov - 28 Nov
8.8/10 Excellent! (2,022 reviews)
"Different area for a motel."

Reviewed on 22 Nov. 2024

La Quinta Inn & Suites by Wyndham Portland
Casco Bay Hotel, Ascend Hotel Collection
Casco Bay Hotel, Ascend Hotel Collection
3.5 out of 5
80 John Roberts Rd., South Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 9 Dec to 10 Dec
AU$119
includes taxes & fees
9 Dec - 10 Dec
8.4/10 Very Good! (2,376 reviews)
"Very good"

Reviewed on 22 Nov. 2024

Casco Bay Hotel, Ascend Hotel Collection
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 Bailey Island holiday package cost?
Custom build your Bailey Island holiday package from an affordable . Pick from any combination of hotels, flights and rental cars to create the getaway you’ve been dreaming about for ages. Be sure to add on some tours and experiences!
How do I get a cheap travel package to Bailey Island?
You’ll save a ton of money if you combine your flights, hotels and car rentals into a Bailey Island holiday package. Sometimes cheap means fewer choices. But that’s not the case with Expedia. We offer over 550 airlines and 1 000 000 properties worldwide, which means you’ll always have plenty of options to choose from. Want to save even more? Add some fun activities to your package deal and unlock even more discounts! After all, travel is about more than just getting to your destination.
How far in advance should I book my Bailey Island holiday?
While prices change from time to time, we generally advise booking your holiday as early as possible. Most international fares are available on Expedia up to a year in advance. If you’re booking late, you might still get lucky. Cheaper tickets to Bailey Island sometimes appear just weeks before departure.
What does an Expedia Bailey Island travel package include?
Flights, hotels and rental cars, or any combination of them — it’s your pick! Whether you’re venturing to Bailey Island with the entire family or adventuring with your friends, there’s a bundle to fit your budget and style. Once you’ve made your booking, why not add on one or two tours as well?
What should I know before booking a Bailey Island travel package?
Whether it’s adventure or relaxation you’re craving, a Bailey Island holiday package lets you organise your escape your way. Plus, you’ll score great discounts when you combine your hotel with your flights and rental car. The more you bundle, the more you’ll save!
Can I choose my airline with a Bailey Island Expedia holiday package?
With a holiday package, you’re in control. Whether you’d like to fly to Bailey Island in coach or first class, simply pick from the available airline options. Expedia has access to over 550 partner airlines worldwide.
If I'm not able to travel, can I cancel my Bailey Island holiday package?
You can cancel your Bailey Island booking if your plans have been upended. Whether you’ll incur a fee or not depends on your hotel, airline or car rental company. You may be able to change or cancel your booking for free if you booked in the last 24 hours. Head to our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.