Bailey Island Vacations from $840

Book a Hotel + Flight or Car together to unlock savings

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.
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Save 100% on your flight
Price was $1,243, price is now $840 per person
$840
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
8.8/10 Excellent! (196 reviews)
We had a really wonderful visit at the Inn at Diamond Cove. It was a special adventure and the staff tried to work with us to help us enjoy our visit after arriving very late at night for a one night /one day stay. We knew nothing about the inn or the island's history so it was a leap of faith and well worth it.

Reviewed on Jun 29, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Save 100% on your flight
Price was $1,394, price is now $916 per person
$916
per person
Aug 15 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Portland (PWM)
9/10 Wonderful! (1,017 reviews)
Room was spotless, staff is friendly and breakfast had lots of options. Convenient location between Wells and Ogunquit. Would stay here again.

Reviewed on Jun 30, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,644, price is now $1,093 per person
$1,093
per person
Aug 15 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Portland (PWM)
8.6/10 Excellent! (1,003 reviews)
This place was amazing. Clean new rooms and very comfortable beds

Reviewed on Jun 23, 2026

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Save 100% on your flight
Price was $1,181, price is now $841 per person
$841
per person
Aug 17 - Aug 20
found 19 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Portland (PWM)
9.6/10 Exceptional! (123 reviews)
Beautiful place to stay in the middle of a quiet street and walking distance to many spots. The rooms and common areas were clean and beautifully maintained. Staff was ready to answer any questions you had via phone or text. I loved this inn and would choose it again. Definitely recommend it !

Reviewed on Jun 6, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,529, price is now $1,169 per person
$1,169
per person
Aug 16 - Aug 19
found 16 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.6/10 Exceptional! (322 reviews)
We just love it there. It is our happy place. Beautiful grounds, comfortable, friendly and downy to earth staff. Wonderful place!

Reviewed on Jun 26, 2026

Don't see what you're looking for?
See all available trips from Columbus to Bailey Island
View all trips

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

Bailey Island Hotel Deals

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
$134 nightly
The price is $148 total per night from Jul 1 to Jul 2
$148 total
Jul 1 - Jul 2
Total with taxes and fees
8.6/10 Excellent! (2,196 reviews)
"Room was not clean at all. The floors were sticky, the bathroom had chewed gum on the floor, used bar soap in the tub, dirt in the tub, and potential dirty towel with blood in it. The room had an odor as well. The staff said they couldn’t help and just told us to email the manager. Not sure if this ..."

Reviewed on Jun 30, 2026

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$349 nightly
The price is $386 total per night from Jul 5 to Jul 6
$386 total
Jul 5 - Jul 6
Total with taxes and fees
9.4/10 Exceptional! (1,775 reviews)
"Clean room but the room wasn't well cleaned during the stay. They picked up towels but I noticed trash on the floor. The 35 facility fee is a joke. Not much to use for 35. If you have breakfast or drinks then the fee is waved. Air conditioning wasn't working. Never got below 74 degrees F in room ..."

Reviewed on Jun 29, 2026

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 refundable
$266 nightly
The price is $294 total per night from Jul 5 to Jul 6
$294 total
Jul 5 - Jul 6
Total with taxes and fees
9.4/10 Exceptional! (1,253 reviews)
"Great location, beautiful, modern rooms with big bathrooms, comfortable beds, spacious areas for storing luggage, etc. and terrific electric black out shades. Very quiet and peaceful. Beautiful garden in the back and easy access to parking garage and Old Port activities. Highly recommend."

Reviewed on Jun 29, 2026

Cambria Hotel Portland Downtown-Old Port
See all 1,855 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Bailey Island vacation package cost?
You can grab a vacation package to this top destination from $840 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.