Bailey Island Vacations from $571

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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.
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
East Bayside
Price was $798, price is now $571 per person
$571
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
18.8/10 Exceptional! (1,118 reviews)
Excellent Hotel and Staff... Would stay here again by choice.

Reviewed on Nov 19, 2025

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,346, price is now $872 per person
$872
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
19.6/10 Exceptional! (86 reviews)
Loved this place and would definitely stay here next time we go back.

Reviewed on Oct 15, 2025

The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,081, price is now $717 per person
$717
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
19.2/10 Exceptional! (249 reviews)
This is in a great location and room was very spacious. Blind in bedroom was broken in down position so it was always dark in there. You are supposed to download an app that requires “always on” connection to Bluetooth to get in, but someone was available to give us card keys instead.

Reviewed on Nov 16, 2025

The Docent's Collection - Boyd Block

The Docent's Collection - Boyd Block

2 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,311, price is now $870 per person
$870
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
20/10 Exceptional! (2 reviews)
Really nice and clean new hotel!

Reviewed on Oct 27, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $901, price is now $631 per person
$631
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Portland (PWM)
18.4/10 Exceptional! (1,668 reviews)
Hotel is so centrally located, you can't beat it. The bar is welcoming and perfect to play cards near the fireplace. Have stayed here a couple times now, and it's the new favorite. Parking is convenient, but a bit pricey at $45/night - but worth the access. Staff are kind and accommodating, rooms are clean and updated.

Reviewed on Nov 20, 2025

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Discover the most popular places to visit in Bailey Island

Bailey Island Bridge

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

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 $571 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.