Bailey Island Holidays

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Your Bailey Island Holiday

With one of our holiday 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 customised Bailey Island holiday on Expedia.

Bailey Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Max Temp Winter
-1.11ºC
Max Temp Summer
21ºC
Top Sights
Thomas Point Beach, Maine State Music Theatre and Sand Beach

Top hotels in Bailey Island

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 £90 per night from 25 Aug to 26 Aug
£90
25 Aug - 26 Aug
includes taxes & fees
7.8/10 Good! (1,088 reviews)
"Staff was friendly and helpful"

Reviewed on 28 Jul 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
The price is £126 per night from 25 Aug to 26 Aug
£126
25 Aug - 26 Aug
includes taxes & fees
7.8/10 Good! (1,038 reviews)
"The lobby is welcoming. I mean spacious, clean and bright!"

Reviewed on 30 Jul 2025

Clarion Hotel Portland
Comfort Inn Airport

Comfort Inn Airport

2.5 out of 5
90 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is £125 per night from 26 Aug to 27 Aug
£125
26 Aug - 27 Aug
includes taxes & fees
8.4/10 Very Good! (1,426 reviews)
"Convenient location to airport and food choices."

Reviewed on 27 Jul 2025

Comfort Inn Airport
See all 1,847 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Bailey Island Bridge

Find out about the history of Bailey Island with a stop at Bailey Island Bridge. Stroll along the seaside or seek out the hiking trails.

Bailey Island Bridge

Frequently asked questions

Why should I book my Bailey Island holiday with Expedia?
Choose Expedia to organise your next adventure easily and all in one place. Our top tip for bagging a terrific deal on a Bailey Island getaway? Bundle your accommodation, flights and/or hire car into a package holiday. Then throw in a few awesome tours and activities. Many bookings also come with flexible cancellation policies, so there's no need to panic if you have to switch up your travel plans. Round-the-clock assistance with making tweaks to your trip is on-hand via our Customer Service Portal link.
When is the best time of year to holiday in Bailey Island?
Love sightseeing but don't like huge crowds? Plan your Bailey Island getaway for November, December and January. Typically, it's much quieter than it is in March, July and August. To give you an idea of the type of weather to expect, the average temperature during the day in January, the coolest time of year in Bailey Island, is -3ºC. The warmest time here is July, when temperatures reach an average of 20ºC.
What is the top hotel for my holiday in Bailey Island?
Kick back and relax in Bailey Island by choosing AC Hotel by Marriott Portland Downtown/Waterfront, ME as your home-away-from-home and gateway to exploration and adventure.
How do I get a cheap holiday to Bailey Island?
If you love getting an amazing deal, combine your bookings into a Bailey Island holiday. Whether you're chasing flights, hotels, hire cars or activities, you can browse and book them all in one place. You'll have endless choice at your fingertips as well. Expedia has over 400 partner airlines and 321,000 properties across the globe to take your pick of. Fly with who you want, book a room where you like and save precious money — now that's the perfect holiday! Learn more about how you can save money on your holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Bailey Island holiday?
There are so many places to visit during your holiday in Bailey Island. Bailey Island Bridge, Lands End Gift Shop, Ash Cove Pottery and Paddleworks are some of this city's most popular attractions.
Do I need a visa for my Bailey Island holiday?
Visa requirements for Bailey Island vary depending on your nationality and purpose of your visit. Be sure to check official government websites to determine if you need a visa for your trip. They'll give you the most up-to-date information, including details about application procedures or supporting documentation that may be necessary. Research your visa requirements well in advance to ensure a smooth travel experience. Finally, make sure your passport is valid for at least six months from the date of your return.
What should I wear on my Bailey Island holiday?
Do a little research into the sorts of clothing people in Bailey Island wear, and maybe even browse social media fashion pages for inspiration. You'll want to create a versatile travel wardrobe filled with pieces that suit your destination and show off your unique style.
What does an Expedia Bailey Island holiday include?
Select from any combination of flights, hire cars and hotels. Once you've made your booking, add the fun stuff like tours and activities. Want to pick your fare class? That's also easy to do. The choice is yours when it comes to planning your ideal Bailey Island trip. Private holiday homes and cottages are a couple of the most highly sought-after property types in Bailey Island. Whatever your group size or holiday style, you can rely on Expedia for the freedom and flexibility to tailor your next dream escape.
Does Expedia offer Book Now, Pay Later Bailey Island holidays?
We certainly do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply click on the payment plan that suits best during the checkout process and take the stress out of budgeting for your next trip. Make sure you bundle your flights, hotel and car hire with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:

  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's convenient payment plans. If paying in multiple instalments sounds right for you, choose this option at checkout.
  • No-deposit holidays: Clicking on the "book now" button is easier with this payment plan. With no upfront fee for your getaway, you can Book Now, Pay Later and start working on your travel itinerary.

Can I choose my airline with a Bailey Island Expedia holiday?
Definitely. Expedia has more than 400 airline partners to pick from globally. With all that choice at your fingertips, finding the right carrier to whisk you away to Bailey Island won't be hard.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.