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Bailey Island

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Cheap Flights to Bailey Island

Fall in love at first flight with your vacation to Bailey Island by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Bailey Island on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Bailey Island, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Bailey Island

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Bailey Island with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the PWM airport.

What is the cheapest month to fly to Bailey Island?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Bailey Island are in , but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Bailey Island?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find  to choose from for your flight to Bailey Island.

What airport is best to fly into Bailey Island?

When you’re planning your trip to Bailey Island, convenience is the name of the game. Luckily, Bailey Island Portland Intl. Jetport Airport is nearby so you can deplane and get going on checking off everything on your Bailey Island must-do list.

How much are flights to Bailey Island?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Bailey Island on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as , you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Bailey Island?

The trick to saving a stack of cash on your flight to Bailey Island? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as  right now, why wait?

Bailey Island Flight Information
Destination airport
Bailey Island
Destination airport IATA code
PWM

Last Minute Hotel Deals in Bailey Island

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the bar and the helpful staff in ...
8.8/10 Excellent! (1,000 reviews)
Clean room and location

Reviewed on Nov 3, 2025

The Westin Portland Harborview
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
7.8/10 Good! (1,222 reviews)
I've stayed here a few times and have always had a good experience. Staff is always welcoming and the rooms are

Reviewed on Nov 9, 2025

Clarion Hotel Portland
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the ...
9.2/10 Wonderful! (1,652 reviews)
Staff was very accommodating and assisted us with a change in rooms due to barking dogs. Beautiful accommodations, easy walk to restaurants and shopping. Would definitely stay here again.

Reviewed on Nov 9, 2025

Portland Harbor Hotel
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road, South Portland, ME
Stay at this hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.8/10 Excellent! (1,600 reviews)
Clean, modern, simple, friendly

Reviewed on Nov 8, 2025

Tru by Hilton Portland Airport Area
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
363 Maine Mall Rd, South Portland, ME
Stay at this hotel in South Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. ...
7.8/10 Good! (1,285 reviews)
Great front desk personnel

Reviewed on Nov 9, 2025

DoubleTree by Hilton Hotel Portland
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

4 out of 5
88 Spring St, Portland, ME
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (1,390 reviews)
Probably the best value for your money out of any of the hotels in downtown portland with an amazing view of the bay super clean room's friendly staff.Nice snack room and breakfast.

Reviewed on Nov 7, 2025

Holiday Inn Portland-By the Bay by IHG
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St, Portland, ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,000 reviews)
clean spacious room

Reviewed on Nov 2, 2025

Fireside Inn & Suites Portland
Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
433 Fore St, Portland, ME
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast ...
8.8/10 Excellent! (1,238 reviews)
Great location!

Reviewed on Nov 6, 2025

Hyatt Place Portland Downtown - Old Port Square
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.