Bailey Island Vacations

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Find the Best Bailey Island Vacation Packages

Bailey Island Hotel Deals

La Quinta Inn & Suites by Wyndham Portland
La Quinta Inn & Suites by Wyndham Portland
2.5 out of 5
340 Park Ave, Portland, ME
Fully refundableReserve now, pay when you stay
The price is SAR 317 per night from Apr 3 to Apr 4
SAR 317
SAR 351 total
includes taxes & fees
3 Apr - 4 Apr
8.8/10 Excellent! (2,109 reviews)
"The staff were super nice, room was clean and welcoming"

Reviewed on 31 March 2025

La Quinta Inn & Suites by Wyndham Portland
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 SAR 539 per night from Apr 6 to Apr 7
SAR 539
SAR 739 total
includes taxes & fees
6 Apr - 7 Apr
9/10 Wonderful! (1,470 reviews)
"The hotel is located in the heart of downtown Portland, right across from the Hyatt. It has an old charm, but the sheets and beds could use some improvement. We stayed during the off-season, so when we arrived, there was plenty of parking right in front of the entrance. However, valet parking was ..."

Reviewed on 27 March 2025

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 refundableReserve now, pay when you stay
The price is SAR 427 per night from Apr 7 to Apr 8
SAR 427
SAR 575 total
includes taxes & fees
7 Apr - 8 Apr
9.2/10 Wonderful! (832 reviews)
"Everything was great"

Reviewed on 31 March 2025

Cambria Hotel Portland Downtown-Old Port
See all 1,687 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.

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 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.

Discover the most popular places to visit in Bailey Island

Bailey Island Bridge

4.5/5(9 reviews)

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

Cobwork Bridge

You can find out about the history of Bailey Island when you stop by Cobwork Bridge. Stroll along the seaside or seek out the hiking trails.

Cobwork Bridge