Bailey Island Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Find the Best Bailey Island Vacation Packages
Bailey Island Hotel Deals
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
￥13,839
￥15,085 total
Sep 16 - Sep 17
includes taxes & fees
6.4/10 (1,124 reviews)
"Property needs some better cleaning in the restrooms. Better maintained n checked coming to toilets and sinks."
Reviewed on Sep 13, 2026
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
￥20,284
￥22,109 total
Sep 14 - Sep 15
includes taxes & fees
8.4/10 Very Good! (3,017 reviews)
"Already contacted the hotel and left a bad review. Issue was with a guest screaming at midnight, but the staff failed and let her back in so she was screaming and carrying on again at 12:30. Would not recommend."
Reviewed on Sep 13, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
￥17,646
￥19,524 total
Sep 20 - Sep 21
includes taxes & fees
8.2/10 Very Good! (1,685 reviews)
"Overall, very comfortable stay would definitely go again"
Reviewed on Sep 13, 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.
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.
Frequently asked questions
How much does a Bailey Island vacation package cost?
You can grab a vacation package to this top destination 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?
Travel in the off-season and you're likely to find cheap Bailey Island vacation packages. Bear in mind that public holidays and major festivals and events can impact prices, so do your research before you go.
How many days is enough for Bailey Island?
You can explore all the leading sights in Bailey Island within a few days, including the must-see Land's End Gift Shop. If you're looking for a longer Bailey Island vacation, look at what sort of activities and day trips are available close by.
Is it worth booking a vacation package to Bailey Island?
Well known for its walking trails and home to leading attractions like Cobwork Bridge, a Bailey Island vacation is bound to impress. Another top sight to check out? Don't miss Bailey Island 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.
How to plan a trip to Bailey Island?
- Choose your travel dates: The things you'd like to do in Bailey Island and your preferred season will help you decide when to travel.
- Set your budget: Factor in costs like flights, transportation and food when calculating how much to set aside for your trip to Bailey Island. Then, pick a hotel that works with your budget, whether that's an affordable option or a lavish retreat.
- Decide how long to go for: Now that you're up to speed on Bailey Island, you can work out the right length of your vacation. Pull together a draft itinerary and allocate enough time to get through everything on your must-do list.
- Combine your airfare and accommodations: After you've nailed down your dates and duration, lock in the perfect Bailey Island vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
