Bailey Island Vacations from $801

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Your Bailey Island Vacation

From its coastal scenery to its spectacular views and beyond, there's a whole lot to like about Bailey Island. Discover the wonders of this exciting city with a Bailey Island vacation package that's tailor-made for you. Every trip to Bailey Island needs a well-designed itinerary. Fill yours with major attractions like Bailey Island Bridge, Lands End Gift Shop and Paddleworks. Your ideal Bailey Island vacation is a few clicks away. Browse hotels, airfares and more on Expedia for a getaway that's tailored to suit your style.

The Latest Bailey Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
Save 100% on your flight
per person
Jul 25 - Aug 1
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
7.6/10 Good! (1,000 reviews)
Arrived a few hours after the “check-in” time but yet there was a long line to check in and was told then our room wasn’t ready. They said it would be about 10 min but it was more like 25. When we got to the floor our room was on they were still cleaning the rooms. They seemed a little disorganized.

Reviewed on Jun 22, 2024

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Jul 25 - Aug 1
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9/10 Wonderful! (1,194 reviews)
Excellent hotel right within walking distance of most everything in downtown Portland

Reviewed on Jun 23, 2024

Microtel Inn & Suites By Wyndham Windham

Microtel Inn & Suites By Wyndham Windham

3 out of 5
per person
Jul 25 - Aug 1
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
8.8/10 Excellent! (999 reviews)
The breakfast was good.

Reviewed on Jun 22, 2024

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
Save 100% on your flight
per person
Jul 25 - Aug 1
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
8/10 Very Good! (1,020 reviews)
Kids had a blast the pool was great for the rainy weather . Will be back again soon

Reviewed on Jun 23, 2024

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Jul 25 - Aug 1
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.4/10 Exceptional! (670 reviews)
We did enjoy the stay very much! Great place with great staff.

Reviewed on Jun 22, 2024

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

Bailey Island Hotel Deals

Casco Bay Hotel, Ascend Hotel Collection
Casco Bay Hotel, Ascend Hotel Collection
3.5 out of 5
80 John Roberts Rd., South Portland, ME
Fully refundableReserve now, pay when you stay
The price is $116 per night from Jun 27 to Jun 28
$116
$127 total
includes taxes & fees
Jun 27 - Jun 28
8.4/10 Very Good! (1,645 reviews)
"Great customer service"

Reviewed on Jun 22, 2024

Casco Bay Hotel, Ascend Hotel Collection
Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is $291 per night from Jul 2 to Jul 3
$291
$360 total
includes taxes & fees
Jul 2 - Jul 3
9/10 Wonderful! (1,208 reviews)
"Loved it"

Reviewed on Jun 22, 2024

Portland Harbor Hotel
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
The price is $116 per night from Jun 24 to Jun 25
$116
$127 total
includes taxes & fees
Jun 24 - Jun 25
7.6/10 Good! (1,016 reviews)
"We could hear a small dog barking for many hours. Other guests were smoking close to the door. A large truck took up many parking spots."

Reviewed on Jun 22, 2024

Days Inn by Wyndham Airport/Maine Mall
See all 1,631 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.

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?
Custom build your Bailey Island vacation package from an affordable $801. Pick from any combination of hotels, flights and rental cars to create the getaway you’ve been dreaming about for ages. Be sure to add on some tours and experiences!
How do I get a cheap travel package to Bailey Island?
You’ll save a ton of money if you combine your flights, hotels and car rentals into a Bailey Island vacation package. Sometimes cheap means fewer choices. But that’s not the case with Expedia. We offer over 550 airlines and 1,000,000 properties worldwide, which means you’ll always have plenty of options to choose from. Want to save even more? Add some fun activities to your package deal and unlock even more discounts! After all, travel is about more than just getting to your destination.
How far in advance should I book my Bailey Island vacation?
While prices change from time to time, we generally advise booking your vacation as early as possible. Most international fares are available on Expedia up to a year in advance. If you’re booking late, you might still get lucky. Cheaper tickets to Bailey Island sometimes appear just weeks before departure.
What does an Expedia Bailey Island travel package include?
Flights, hotels and rental cars, or any combination of them — it’s your pick! Whether you’re venturing to Bailey Island with the entire family or adventuring with your friends, there’s a bundle to fit your budget and style. Once you’ve made your booking, why not add on one or two tours as well?
What should I know before booking a Bailey Island travel package?
Whether it’s adventure or relaxation you’re craving, a Bailey Island vacation package lets you organize your escape your way. Plus, you’ll score great discounts when you combine your hotel with your flights and rental car. The more you bundle, the more you’ll save!
Can I choose my airline with a Bailey Island Expedia vacation package?
With a vacation package, you’re in control. Whether you’d like to fly to Bailey Island in coach or first class, simply pick from the available airline options. Expedia has access to over 550 partner airlines worldwide.
If I'm not able to travel, can I cancel my Bailey Island vacation package?
You can cancel your Bailey Island booking if your plans have been upended. Whether you’ll incur a fee or not depends on your hotel, airline or car rental company. You may be able to change or cancel your booking for free if you booked in the last 24 hours. Head to our Customer Service Portal for more information.

Discover the most popular places to visit in Bailey Island

Image for Bailey Island Bridge

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
Image for Land's End Gift Shop

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
Image for Cobwork Bridge

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

Other vacations you might like

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