Bailey Island Holidays

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Your Bailey Island Holiday

With one of our holiday packages to Bailey Island, you'll have limitless opportunities for adventure and relaxation. There's a lot to look forward to, including its coastal scenery and spectacular views. If your trip to Bailey Island includes a little sightseeing, drop by well-known attractions like Bailey Island Bridge, Lands End Gift Shop and Eagle Island. Your Bailey Island holiday is clicks away. Explore hotels, airfares and more on Expedia for an adventure that's tailored just for you.

Bailey Island Holiday

Bailey Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Max Temp Winter
-1.11ºC
Max Temp Summer
21ºC
Top Sights
Sand Beach, Thomas Point Beach and Wolfes Neck Woods State Park

Our pick of the best Bailey Island Hotel Deals

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

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

3 out of 5
340 Park Ave Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$215 per night from 1 July to 2 July
AU$215
1 July - 2 July
includes taxes & fees
8.6/10 Excellent! (2,195 reviews)
"The bed sheets were dirty, hair and stains. I have a strong feeling that they were not changed. Everything else was fine."

Reviewed on 30 June 2026

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

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$510 per night from 5 July to 6 July
AU$510
5 July - 6 July
includes taxes & fees
9.4/10 Exceptional! (1,775 reviews)
"Clean room but the room wasn't well cleaned during the stay. They picked up towels but I noticed trash on the floor. The 35 facility fee is a joke. Not much to use for 35. If you have breakfast or drinks then the fee is waved. Air conditioning wasn't working. Never got below 74 degrees F in room ..."

Reviewed on 29 June 2026

Portland Harbor Hotel
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
The price is AU$441 per night from 5 July to 6 July
AU$441
5 July - 6 July
includes taxes & fees
9.4/10 Exceptional! (1,252 reviews)
"Great location, beautiful, modern rooms with big bathrooms, comfortable beds, spacious areas for storing luggage, etc. and terrific electric black out shades. Very quiet and peaceful. Beautiful garden in the back and easy access to parking garage and Old Port activities. Highly recommend."

Reviewed on 29 June 2026

Cambria Hotel Portland Downtown-Old Port
See all 1,855 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular Bailey Island attractions

Bailey Island Bridge

9.2/5 (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.
See properties

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?

  1. 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.
  2. 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.
  3. 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.
  4. Combine your airfare and accommodation: After you've nailed down your dates and duration, lock in the perfect Bailey Island holiday package for you.

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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.