
Bailey Island Vacations from $683
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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.


Evalina Hotel
Downtown Portland
$1,792
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
10/10 Exceptional! (7 reviews)
It was our first time visiting Portland, and the Evalina exceeded our expectations. The location is perfect, right on Commercial Street, with plenty of restaurants and shops nearby. The ferry and cruise ports are also just a 5–10 minute walk away, making it easy to visit the different islands.
The suite was comfortable and thoughtfully equipped with everything we could need, including an umbrella for rainy days, coffee and a French press, tea, a washer and dryer, and so much more. Communication was excellent throughout our stay as well.
We truly enjoyed our visit, and the next time we’re in Portland, the Evalina will be our first choice!
Reviewed on Aug 8, 2026

Ogunquit River Inn & Suites
Moody
$939
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9/10 Wonderful! (1,017 reviews)
We checked in a bit early, and we were greeted with ice tea and a smile. A very nice group of folks working and the breakfast was better than expected. We would absolutely stay here again.
Reviewed on Aug 11, 2026


Inn at Diamond Cove
$1,253
per person
Sep 10 - Sep 14
found 15 hours ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
8.8/10 Excellent! (202 reviews)
Our anniversary was ruined at the Inn at Diamond Cove!! We called in advance to have a golf cart available to take us to the resort and when we arrived there was no shuttle. We called the hotel again and 20 minutes later it arrived. We traveled to this location to enjoy the jacuzzi and the jacuzzi heater was broken. We tried to go to sleep at 11 p.m. and a noise was thudding above our heads for an hour. Then, the noise started again at 5 a.m. I called the front desk 6 times from the room phone and there was no answer!!! So, in pajamas I walked down to the front desk and the woman started screeching at me that she got my calls... but their phone system didn't work and I should have known that... and the noise was not her problem! I told her that a guest should not have to stumble out of bed to talk to the front desk and I asked for a refund, to which she agreed, I then emailed the hotel manager and they refused to give me any compensation!! DO NOT STAY AT THIS HOTEL!! They take no responsibility for a terrible guest experience and they STINK!!!!!
Reviewed on Aug 11, 2026
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View all tripsStay 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.
Land's End Gift Shop
10.0/10 (1 review)
Perched at Bailey Island's southern tip, this charming shop offers an array of Maine-made treasures. Browse two levels of local crafts and specialty foods while enjoying Casco Bay views from the rocky coastline.
Cobwork Bridge
10.0/10 (1 review)
The Bailey Island Bridge's unique granite cribstone design allows tides to flow freely through its structure. Drive across this engineering marvel for stunning Casco Bay views—America's only bridge of its kind.
Bailey Island Hotel Deals

Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
$93 nightly
$101 total
Sep 10 - Sep 11
Total with taxes and fees

Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
$96 nightly
$105 total
Aug 18 - Aug 19
Total with taxes and fees
6.4/10 (1,044 reviews)
"The room had a horrible smell. The door didn’t lock. There were holes in the wall covered in spackling."
Reviewed on Aug 11, 2026

Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$131 nightly
$145 total
Sep 1 - Sep 2
Total with taxes and fees
8/10 Very Good! (1,624 reviews)
"It did the job for 3 nights. A little out dated, the mattress felt like a old school spring bed. Bathroom small and could have been updated. Positive: pricing, close to Thompson Point, and cheap Uber to downtown Portland"
Reviewed on Aug 10, 2026
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 $683 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.
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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.



















