Bailey Island Vacations from $823
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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.
Blind Tiger Portland - Danforth Street.
West End
$915
per person
Sep 21 - Sep 24
just found
Roundtrip flight included
New York (JFK) to Portland (PWM)
9.6/10 Exceptional! (189 reviews)
This hotel is amazing. The rooms, beds, and all the details are so incredible. I wish I could have stayed longer. Check in was a breeze as well. You can tell they take a lot of care and thought into the property. I will definitely be back
Reviewed on Jul 25, 2026
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Bailey Island Bridge
9.2/10 (10 reviews)
The world's only cribstone bridge connects Bailey Island with unique granite slabs that allow tides to flow freely. Drive or walk across this 1926 engineering marvel for spectacular coastal views.
Land's End Gift Shop
10.0/10 (1 review)
Perched at Bailey Island's southern tip, this charming shop offers an array of Maine-made treasures. Browse two levels of local crafts and specialty foods while enjoying Casco Bay views from the rocky coastline.
Cobwork Bridge
10.0/10 (1 review)
The Bailey Island Bridge's unique granite cribstone design allows tides to flow freely through its structure. Drive across this engineering marvel for stunning Casco Bay views—America's only bridge of its kind.
Bailey Island Hotel Deals
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
$77 nightly
$83 total
Sep 1 - Sep 2
Total with taxes and fees
7.2/10 Good! (703 reviews)
"Clean. Breakfast was pretty good. Excellent parking. Fridge and microwave in room which was nice. There was a pool but we did not partake but it looked to be in good form. Close to the Interstate and right on Hwy. 1. Room I think had been recently redone, so the decor was nice. The only reason that ..."
Reviewed on Aug 19, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$131 nightly
$145 total
Sep 1 - Sep 2
Total with taxes and fees
8/10 Very Good! (1,629 reviews)
"Hotel is a bit older but maintained well and clean."
Reviewed on Aug 19, 2026
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
$96 nightly
$104 total
Sep 9 - Sep 10
Total with taxes and fees
6.4/10 (1,070 reviews)
"Staff was plesant. Adequate parking. Room cleanliness, especially in the bathroom and kitchenette are was less than desirable. AC unit and filters showed excess mold growth. Locks for door were damaged and lock in back bedroom did not work at all. Toilet seat was wrong shape and size for the actual ..."
Reviewed on Aug 19, 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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Frequently asked questions
How much does a Bailey Island vacation package cost?
You can grab a vacation package to this top destination from $823 on Expedia. But how much your vacation to Bailey Island costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Bailey Island?
November, December and January are the best times to look for cheap Bailey Island vacation packages. Opting to travel in quieter months means you can generally find lower prices on accommodations and flights.
How many days is enough for Bailey Island?
You can easily see all the leading attractions in Bailey Island in a few days, including the popular Land's End Gift Shop. If you want a longer Bailey Island vacation, check out what sort of day trips and activities are available close by.
Is it worth booking a vacation package to Bailey Island?
Known for its walking trails and home to popular attractions like Bailey Island Bridge, a Bailey Island vacation is sure to impress. Another top sight worth exploring? Don't miss Cobwork Bridge.
How to find the best Bailey Island package deals?
Use Expedia's filter tool to find some of the best Bailey Island package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Bailey Island package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Bailey Island vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Bailey Island vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Bailey Island?
Secure incredible discounts by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Bailey Island getaway.
Does Expedia offer Book Now, Pay Later Bailey Island vacation packages?
Secure your perfect escape to Bailey Island with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait for your next payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to stick to your budget and snap up travel deals before they disappear.
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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.
