Bailey Island Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SAR 5,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Bailey Island Vacation Packages

Bailey Island Hotel Deals

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
The price is SAR 544 per night from Jul 26 to Jul 27
SAR 544
SAR 602 total
26 Jul - 27 Jul
includes taxes & fees
8.2/10 Very Good! (1,011 reviews)
"The price is fair and clean"

Reviewed on 21 July 2026

Fireside Inn & Suites Portland
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 SAR 672 per night from Jul 26 to Jul 27
SAR 672
SAR 743 total
26 Jul - 27 Jul
includes taxes & fees
8.6/10 Excellent! (2,194 reviews)
"always a great stay here"

Reviewed on 21 July 2026

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
The price is SAR 603 per night from Aug 3 to Aug 4
SAR 603
SAR 667 total
3 Aug - 4 Aug
includes taxes & fees
Clarion Hotel Portland Airport ME
See all 1,962 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.

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.
See properties

Frequently asked questions

How much does a Bailey Island vacation package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a vacation to Bailey Island costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Bailey Island?
The off-season is the best time to head to Bailey Island if you're trying to keep costs down. Another tip for scoring cheap Bailey Island vacation packages? Avoid visiting during public holidays and any major events.
How to find the best Bailey Island package deals?
Bagging a cheap Bailey Island package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most affordable Bailey Island package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book a Bailey Island vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels individually. Better still, you can customize your Bailey Island escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Bailey Island?
If you have your Bailey Island travel dates locked in, book early to bag some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for traveling on a whim.
How to plan a trip to Bailey Island?

  1. Choose when to travel: Check your schedule and get your bags packed. Your preferred time of year and the available activities will also help you decide when to escape to Bailey Island.
  2. Figure out your budget: Ensure you have enough money to pay for everything from food and transportation to activities and flights. Your accommodations will likely be the biggest expense during your trip to Bailey Island.
  3. Decide how long to go for: Now that you're more familiar with Bailey Island, you can figure out the right length of your break. Pull together a draft plan and allocate enough time to cover everything you want to see.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to find a Bailey Island vacation package that brings all your bookings together.