Bailey Island Vacations from $448
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Your Bailey Island Vacation
With one of our vacation packages to Bailey Island, you'll have endless opportunities for relaxation and adventure. There's lots to experience, including its coastal scenery and spectacular views. If sightseeing is on the cards during your trip to Bailey Island, check out popular attractions like Bailey Island Bridge, Lands End Gift Shop and Ragged Island. A few quick clicks is all it takes to build a customized Bailey Island vacation on Expedia.
The Latest Bailey Island vacation packages
Price found within the past 48 hours. Click for updated prices.
The Meadowmere Resort
Price was $787, price is now $577 per person
$577
per person
Sep 18 - Sep 20
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
I requested a room accessible for my 90 year old mother with a walker. We got that. I asked the front desk woman if there was another entrance to the pool because the one at the entrance had many stairs. She said no. Another traveler in the lobby told me there is one around the back. The staff member said they never took her around the property and trained her when the woman said that. They play music all day and night until 10:30pm outside my room by a speaker. I requested it be turned off and a different front desk member said he didn't know how and the maintenance guy hadn't been there for 2 weeks. I got a text when I arrived to say to text with any questions, but when I texted I got no answer. I asked for early check in which they did. Then they charged me $20 for it without telling me there was a charge at the time.
Reviewed on Jul 22, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was $1,002, price is now $760 per person
$760
per person
Sep 1 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.6/10 Exceptional! (188 reviews)
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.
Reviewed on Jun 26, 2026
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Bailey Island Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$144 nightly
The price is $159 total per night from Aug 3 to Aug 4
$159 total
Aug 3 - Aug 4
Total with taxes and fees
8.2/10 Very Good! (1,572 reviews)
"We never finalized the booking and never checked in, The reservation does not show up on my account so not sure how it got booked. They charged us for the room anyway!"
Reviewed on Jul 25, 2026
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$254 nightly
The price is $281 total per night from Aug 23 to Aug 24
$281 total
Aug 23 - Aug 24
Total with taxes and fees
9/10 Wonderful! (1,008 reviews)
"Great location, very walkable to food and activities."
Reviewed on Jul 25, 2026
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $167 total per night from Jul 26 to Jul 27
$167 total
Jul 26 - Jul 27
Total with taxes and fees
8.2/10 Very Good! (1,019 reviews)
"Amazing! Love the place !"
Reviewed on Jul 24, 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.
Find the Best Bailey Island Vacation Packages
Bailey Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
Max Temp Winter | 30ºF |
Max Temp Summer | 70ºF |
Top Sights | Thomas Point Beach, Sand Beach and Wolfes Neck Woods State Park |
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- Hunnewell Beach
- Freeport Vacations
- Wolfe's Neck Woods State Park
- Harrington House
- Two Lights State Park
- Visit Portland
- Bowdoin College
- Cundys Harbor Vacations
- Little John Island Preserve
- Popham Beach State Park
- Victoria Mansion
- Visit Freeport
- Ll Bean Flagship Store
- Casco Bay
- Wilbur's of Maine Chocolate Confections
- Downtown Portland Vacations
- Chebeague Island Vacations
- Sebasco Estates Vacations
- Bailey Island Bridge
- Casco Bay Lines Ferry Terminal
- Visit Bailey Island
- Fort Williams Park
- Visit Old Port
- Land's End Gift Shop
- Bug Light
- Bates-Morse Mountain Conservation Area
- Portland Head Light
- Bradbury Mountain State Park
- First Parish Church
- East End Beach
- Paddleworks
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
