Bailey Island Vacations from $488

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Your Bailey Island Vacation

With one of our vacation packages to Bailey Island, you'll have endless opportunities for relaxation and adventure. There's lots to experience, including its coastal scenery and spectacular views. If sightseeing is on the cards during your trip to Bailey Island, check out popular attractions like Bailey Island Bridge, Lands End Gift Shop and Ragged Island. A few quick clicks is all it takes to build a customized Bailey Island vacation on Expedia.

The Latest Bailey Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Save 100% on your flight
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
8.8/10 Excellent! (793 reviews)
The staff were friendly and helpful. The Inn was clean and in a convenient location. Trolley pick up was right out front of the Inn to take us to the downtown area and beach. Enjoyed the pool. We did not take advantage of the river kayaking/paddle boarding. Next trip.

Reviewed on Jul 10, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (1,003 reviews)
Everything about this location is five stars

Reviewed on Jul 6, 2025

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
per person
Aug 27 - Aug 31
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (585 reviews)
We had a very enjoyable 4 night stay here. We stayed in the Nathanial Lord Mansion and our room was clean, stylish and very comfortable. Breakfast was served each morning in our mansion and was very nice with a different hot option every day. The inn is located within very easy walking distance of everything Kennebunkport has to offer - shops, cafes and restaurants. All in all an excellent stay and highly recommended!

Reviewed on Jul 8, 2025

Nautical Mile

Nautical Mile

2.5 out of 5
Save 100% on your flight
per person
Aug 14 - Aug 18
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.4/10 Very Good! (12 reviews)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.2/10 Wonderful! (1,533 reviews)
The staff were super friendly and helpful. The room was beautiful and the garden atmosphere was fantastic. I would recommend this hotel.

Reviewed on Jul 10, 2025

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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

Bailey Island Hotel Deals

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
$129 nightly
The price is $141 total per night from Jul 13 to Jul 14
$141 total
Jul 13 - Jul 14
Total includes taxes and fees
7.8/10 Good! (1,011 reviews)
"Great for the price, clean rooms and good breakfast"

Reviewed on Jul 10, 2025

Days Inn by Wyndham Airport/Maine Mall
Clarion Hotel Portland
Clarion Hotel Portland
2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $168 total per night from Jul 14 to Jul 15
$168 total
Jul 14 - Jul 15
Total includes taxes and fees
7.8/10 Good! (1,015 reviews)
"Nice hotel close to the airport with shuttle service"

Reviewed on Jul 7, 2025

Clarion Hotel Portland
Ramada Plaza by Wyndham Portland
Ramada Plaza by Wyndham Portland
3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $171 total per night from Jul 21 to Jul 22
$171 total
Jul 21 - Jul 22
Total includes taxes and fees
7.6/10 Good! (1,030 reviews)
"Quick check in. The staff has been very helpful. I am on a motorcycle, it has been raining, they offered towels to dry the bike and found some towels i could take with me, as my seat is very soggy."

Reviewed on Jul 10, 2025

Ramada Plaza by Wyndham Portland
See all 1,803 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.

Find the Best Bailey Island Vacation Packages

Bailey Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Max Temp Winter
30ºF
Max Temp Summer
70ºF
Top Sights
Thomas Point Beach, Sand Beach and Wolfes Neck Woods State Park

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Frequently asked questions

How much does a Bailey Island vacation package cost?
You can grab a vacation package to this top destination from $488 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?
November, December and January are the best times to look for cheap Bailey Island vacation packages. Opting to travel in quieter months means you can generally find lower prices on accommodations and flights.
How many days is enough for Bailey Island?
You can easily see all the leading attractions in Bailey Island in a few days, including the popular Land's End Gift Shop. If you want a longer Bailey Island vacation, check out what sort of day trips and activities are available close by.
Is it worth booking a vacation package to Bailey Island?
Known for its walking trails and home to popular attractions like Bailey Island Bridge, a Bailey Island vacation is sure to impress. Another top sight worth exploring? Don't miss Cobwork 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.
Does Expedia offer Book Now, Pay Later Bailey Island vacation packages?
Secure your perfect escape to Bailey Island with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait for your next payday --- we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to stick to your budget and snap up travel deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.