Bailey Island Vacations from $585
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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.
Nautical Mile
$585
per person
Nov 2 - Nov 9
found 19 hours ago
Roundtrip flight included
Charleston (CHS) to Portland (PWM)
8.6/10 Excellent! (24 reviews)
I've stayed at the Nautical Mile many times! The rooms are perfect for a get-away! The pool is always ready to cool off in and the people, both working at the Nautical Mile and guests are very friendly.
Reviewed on Sep 8, 2026
Blind Tiger Portland - Danforth Street.
West End
$1,417
per person
Nov 30 - Dec 7
found 18 hours ago
Roundtrip non-stop flight included
Charleston (CHS) to Portland (PWM)
9.6/10 Exceptional! (192 reviews)
Place was charming and quirky. Very comfortable and well located.
Reviewed on Sep 18, 2026
Stay near popular Bailey Island attractions
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
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundableReserve now, pay when you stay
$90 nightly
$98 total
Oct 18 - Oct 19
Total with taxes and fees
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
$110 nightly
$120 total
Oct 18 - Oct 19
Total with taxes and fees
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
$108 nightly
$119 total
Oct 18 - Oct 19
Total with taxes and fees
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 $585 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.
Explore a world of travel with Expedia
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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.
