Bailey Island Vacations

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Find the Best Bailey Island Vacation Packages

Bailey Island Hotel Deals

Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is NT$4,560 per night from Aug 11 to Aug 12
NT$4,560
NT$5,046 total
Aug 11 - Aug 12
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"Breakfast food served out of a closet was a little odd, but it did taste good."

Reviewed on 2025/8/1

Clarion Hotel Portland
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is NT$3,287 per night from Aug 24 to Aug 25
NT$3,287
NT$3,582 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,108 reviews)
"It was a nice place. The food was limited and the pool could use a cleaning but not to bad. Overall it was a good experience"

Reviewed on 2025/8/1

Days Inn by Wyndham Airport/Maine Mall
Comfort Inn Airport

Comfort Inn Airport

2.5 out of 5
90 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is NT$4,019 per night from Aug 5 to Aug 6
NT$4,019
NT$4,381 total
Aug 5 - Aug 6
includes taxes & fees
8.4/10 Very Good! (1,444 reviews)
"Very friend staff"

Reviewed on 2025/8/1

Comfort Inn Airport
See all 1,827 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.

Discover the most popular places to visit in Bailey Island

Bailey Island Bridge

Find out about the history of Bailey Island when you spend time at Bailey Island Bridge. Stroll along the seaside or seek out the hiking trails.

Bailey Island Bridge

Land's End Gift Shop

Enjoy an outing to Land's End Gift Shop during your stay in Bailey Island. While you're in the area, find time to visit its shops.

Land's End Gift Shop

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?

  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 vacation. Pull together a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. 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.