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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

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

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$139 per night from 15 Mar to 16 Mar
AU$139
15 Mar - 16 Mar
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
Location, clean rooms, pleasant staff

Reviewed on 23 Feb 2026

The Westin Portland Harborview
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$121 per night from 5 Mar to 6 Mar
AU$121
5 Mar - 6 Mar
includes taxes & fees
8/10 Very Good! (1,380 reviews)
Comfortable bed and pillows. Disappointed that the airport shuttle started running so late and we had to pay for Uber ride for morning flight. Those hours maybe should be listed. Otherwise nice.

Reviewed on 24 Feb 2026

Clarion Hotel Portland Airport ME
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,776 reviews)
Location was great, staff was friendly (especially adam at the front desk) but the bed was very uncomfortable, pillows were cheap and deflated, and the whole "resort fee" was very offputting. I would rather just be told a real rate when I book over getting an extra few hundred in charges. The 35$ ...

Reviewed on 23 Feb 2026

Portland Harbor Hotel
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.