Bailey Island Holidays
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- Better togetherSave up to €900 when you book a flight and hotel together*
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Top hotels in Bailey Island
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
€82
4 Nov - 5 Nov
includes taxes & fees
8.2/10 Very good! (1,773 reviews)
"I stayed here for a conference in town because it was convenient and the price was so much more reasonable than the ridiculous situation going on in the Old Port. I can’t believe people are truly willing to spend +500$ a night to stay in a city in Maine in a Monday, but that’s what it’s come to. ..."
Reviewed on 13 Oct 2026
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
€126
11 Nov - 12 Nov
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Excellent breakfast! Must include if you are able to! We honestly found parking on the street for free each night if you don’t mind hunting for a spot and walking a tad. Worth saving on parking in my opinion."
Reviewed on 13 Oct 2026
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
€98
25 Oct - 26 Oct
includes taxes & fees
8.2/10 Very good! (1,013 reviews)
"Everything was clean and well maintained. Rustic charm We like the fact that the hot tub cool and so on were open till 11:00 p.m. And the grab and go breakfast was also available until 11:00 a.m. which is nice because when you're on vacation you sometimes keep odd hours and it's nice when there are ..."
Reviewed on 13 Oct 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 speciality 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 holiday package cost?
You can grab a holiday package to this top destination on Expedia. But how much your holiday 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 holiday 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 holiday, look at what sort of activities and day trips are available close by.
Is it worth booking a holiday package to Bailey Island?
Well known for its walking trails and home to leading attractions like Cobwork Bridge, a Bailey Island holiday 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 holiday package well in advance.
Is it cheaper to book a Bailey Island holiday as a package?
Expedia holiday 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 personalised Bailey Island holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday 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 holiday. Pull together a draft itinerary and allocate enough time to get through everything on your must-do list.
- Combine your airfare and accommodation: After you've nailed down your dates and duration, lock in the perfect Bailey Island holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
