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.

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

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
The price is AU$336 per night from 25 May to 26 May
AU$336
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (1,769 reviews)
Hotel is beautiful but rooms are small! Tight for 3 people. The parking is expensive and only option is valet. There’s always a long wait to get your car, they don’t go in order and are rude. The “free” snacks on the various floors were nothing special. Instead of sparkling water, have regular available. ...

Reviewed on 13 May 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
The price is AU$250 per night from 27 May to 28 May
AU$250
27 May - 28 May
includes taxes & fees
9.4/10 Exceptional! (1,651 reviews)
A hotel has control over cleanliness, upkeep, and service. This hotel ranks very poorly in service. Not a single smile from any staff at check-in, check-out, or requests. They advertise pickup from the airport is available but after a call before flight, after landing, and then 3 more calls after ...

Reviewed on 12 May 2026

Portland Regency Hotel & Spa
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
The price is AU$292 per night from 26 May to 27 May
AU$292
26 May - 27 May
includes taxes & fees
9.4/10 Exceptional! (1,216 reviews)
Best customer service I have ever received.

Reviewed on 13 May 2026

Cambria Hotel Portland Downtown-Old Port
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.

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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.