Search Cheap Flights to
Bailey Island

Name: Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
Rating: 8.4

A green netted buoy attached to a wooden post by a curved metal hook, with a wooden fence and a body of water in the background.

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Bailey Island Flights as Low as $165

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

All deals

One way

Roundtrip

Tue, Sep 8 - Sat, Sep 12

EWR

Newark Liberty Intl. Airport

PWM

Portland Intl. Jetport

$165

Roundtrip

found 17 hours ago

Tue, Sep 8 - Sat, Sep 12

EWR

Newark Liberty Intl. Airport

PWM

Portland Intl. Jetport

$183

Roundtrip

found 17 hours ago

Tue, Sep 8 - Sat, Sep 12

EWR

Newark Liberty Intl. Airport

PWM

Portland Intl. Jetport

$226

Roundtrip

found 17 hours ago

Tue, Sep 8 - Sat, Sep 12

EWR

Newark Liberty Intl. Airport

PWM

Portland Intl. Jetport

$238

Roundtrip

found 17 hours ago

Fri, Sep 11 - Tue, Sep 15

EWR

Newark Liberty Intl. Airport

PWM

Portland Intl. Jetport

$241

Roundtrip

found 1 day ago

Sun, Sep 6 - Sat, Sep 12

EWR

Newark Liberty Intl. Airport

PWM

Portland Intl. Jetport

$243

Roundtrip

found 1 day ago

Sun, Sep 6 - Wed, Sep 9

EWR

Newark Liberty Intl. Airport

PWM

Portland Intl. Jetport

$246

Roundtrip

found 1 day ago

Tue, Jul 7 - Fri, Jul 10

DCA

Ronald Reagan Washington National

PWM

Portland Intl. Jetport

$250

Roundtrip

found 1 day ago

Wed, Sep 9 - Sat, Sep 12

EWR

Newark Liberty Intl. Airport

PWM

Portland Intl. Jetport

$251

Roundtrip

found 1 day ago

Sun, Sep 6 - Sat, Sep 19

FAY

Fayetteville Regional

PWM

Portland Intl. Jetport

$307

Roundtrip

found 1 day ago

Sat, Aug 22 - Fri, Aug 28

CLT

Charlotte-Douglas Intl.

PWM

Portland Intl. Jetport

$345

Roundtrip

found 6 days ago

Tue, Aug 11 - Tue, Aug 18

AUS

Austin-Bergstrom Intl.

PWM

Portland Intl. Jetport

$363

Roundtrip

found 1 day ago

Tue, Sep 8 - Tue, Sep 15

FAY

Fayetteville Regional

PWM

Portland Intl. Jetport

$379

Roundtrip

found 1 day ago

Wed, Jul 1 - Sat, Jul 4

CHA

Chattanooga Metropolitan

PWM

Portland Intl. Jetport

$399

Roundtrip

found 1 day ago

Wed, Mar 3 - Thu, Mar 11

PHX

Sky Harbor Intl.

PWM

Portland Intl. Jetport

$433

Roundtrip

found 4 days ago

Wed, Aug 12 - Sun, Aug 16

AUS

Austin-Bergstrom Intl.

PWM

Portland Intl. Jetport

$620

Roundtrip

found 1 day ago

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 September, 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 14 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 $165, 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 $165 right now, why wait?

Bailey Island Flight Information
Destination airport	Portland Intl. Jetport
Destination airport IATA code	PWM
Roundtrip price	$165

Last Minute Hotel Deals in Bailey Island

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

340 Park Ave Portland ME

Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...

8.6/10 Excellent! (2,193 reviews)

"The staff were very nice. I did find it odd that they charged a parking fee, given their location."

Reviewed on Jun 26, 2026

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Portland Harbor Hotel

468 Fore Street Portland ME

Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff ...

9.4/10 Exceptional! (1,773 reviews)

"Iron broken. Construction outside."

Reviewed on Jun 26, 2026

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Cambria Hotel Portland Downtown-Old Port

25 HANCOCK STREET Portland ME

Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...

9.4/10 Exceptional! (1,251 reviews)

"The size of the room and proximity to Old Town were good. However, the view was to the office building next door and our room did not get cleaned while we were there for 2 nights. The room and average breakfast were too expensive for what we got."

Reviewed on Jun 27, 2026

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Clarion Pointe South Portland

675 Main Street I-95 South Portland ME

Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's ...

7.4/10 Good! (509 reviews)

"Hideous hotel. They charged top dollar for a dilapidated, poorly re-decorated Version of a pig with lipstick. Hall floors uneven and a tripping hazard, our room had bubbled paint on the walls from water leaks, the floor was poorly laid plastic plans, uneven and cracked. No bar soap, thin walls and ..."

Reviewed on Jun 27, 2026

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Portland Regency Hotel & Spa

20 Milk Street Portland ME

Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...

9.4/10 Exceptional! (1,674 reviews)

"Lovely place to stay by everything. Beautiful old building with some charm. Bar is swanky and a dive atmosphere at the same time. Beds were sooo comfortable. Only downside is jacuzzi isn’t open during convenient hours."

Reviewed on Jun 27, 2026

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Comfort Inn South Portland Airport

90 Maine Mall Rd South Portland ME

Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...

8.6/10 Excellent! (2,161 reviews)

"Perfect for a stay before a flight! Shuttle service and $10 a night parking while away."

Reviewed on Jun 27, 2026

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Quality Inn & Suites South Portland

738 Main Street South Portland ME

Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...

6.6/10 (1,006 reviews)

"The hotel needs updated and cleaned thoroughly. The floors were dirt and sticky feeling and the bathrooms were super small and not clean (shower leaked on the floor). The rooms were musty smelling and damp feeling. Doors would not unlock with keycard and had to go to the office twice to get a key ..."

Reviewed on Jun 27, 2026

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Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

80 John Roberts Rd. South Portland ME

Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...

8.4/10 Very Good! (2,962 reviews)

"Honestly the place wasn’t bad, I just needed a one night stay after surgery so I didn’t require many amenities. It was clean and bed was comfortable. The only bad thing is that the rooms are no where near sound proof. You can hear every single thing happening in the hallway and in the rooms next ..."

Reviewed on Jun 27, 2026

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See all 1,849 properties in Bailey Island

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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