Bailey Island Vacations from $647

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

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.
Saco Bay Hotel

Saco Bay Hotel

2.5 out of 5
Save 100% on your flight
Price was $969, price is now $647 per person
$647
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
7.6/10 Good! (1,051 reviews)
The internet was not secure The room did not have room darkening drapes. Breakfast was good. TV not usefall no NBC,ABC,CBS channel and very few other channels to watch except old out of date programming.

Reviewed on May 11, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Save 100% on your flight
Price was $1,578, price is now $951 per person
$951
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9/10 Wonderful! (1,003 reviews)
Very convenient and helpful staff.

Reviewed on May 10, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,973, price is now $1,219 per person
$1,219
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
8.6/10 Excellent! (1,001 reviews)
Clean room , friendly Staff , Breakfast was great !!

Reviewed on May 13, 2026

Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
Save 100% on your flight
Price was $1,362, price is now $919 per person
$919
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (341 reviews)
IT WAS CHARMING AND BEAUTIFUL. The restaurant was wonderful, all the staff was first class, would love to go back.

Reviewed on Oct 14, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,490, price is now $1,017 per person
$1,017
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (1,753 reviews)
Great hotel with great staff!

Reviewed on May 12, 2026

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

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

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
$241 nightly
The price is $266 total per night from May 25 to May 26
$266 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (1,767 reviews)
Great hotel with great staff!

Reviewed on May 12, 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$166 nightly
The price is $183 total per night from May 27 to May 28
$183 total
May 27 - May 28
Total with taxes and fees
9.4/10 Exceptional! (1,651 reviews)
A hotel has control over cleanliness, upkeep, and service. This hotel ranks very poorly in service. Not a single smile from any staff at check-in, check-out, or requests. They advertise pickup from the airport is available but after a call before flight, after landing, and then 3 more calls after ...

Reviewed on May 12, 2026

Portland Regency Hotel & Spa
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
$177 nightly
The price is $196 total per night from May 26 to May 27
$196 total
May 26 - May 27
Total with taxes and fees
9.4/10 Exceptional! (1,214 reviews)
Very clean and modern design, spacious room and overall the place was very quiet and made for a good night's sleep. Convenient to have the garage attached to the hotel, you just have to have your ticket validated by the front desk, but allows you to come and go as you please for the parking fee.

Reviewed on May 12, 2026

Cambria Hotel Portland Downtown-Old Port
See all 1,824 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 $647 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.