Search Resorts in Bailey Island

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Compare 2 Resorts in Bailey Island with updated reviews, rates, and availability.

Once in a lifetime opportunity to rent the Chebeague Island Inn
Dining
Once in a lifetime opportunity to rent the Chebeague Island Inn
Once in a lifetime opportunity to rent the Chebeague Island Inn
Bates Island: Casco Bay Glamping Experience
Bates Island: Casco Bay Glamping Experience
Bates Island: Casco Bay Glamping Experience
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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.
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Other property types in Bailey Island

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
THE GILLS GROUP has two additional cottages available for larger groups
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
10.0 out of 10, Exceptional, (98)
"All was good except the bedroom with the waterbed-like frame. It was uncomfortable. Also not air conditioned. We could have used a dishwasher. The setting was great. Overall, it was a good experience."
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
9.8 out of 10, Exceptional, (6)
"Overall this location is a great spot for those that dont need many amenities. There is no tv and no ac but the view and the breeze from the water make up for that! The space was clean and there was a grill plus Cooks Lobster house was a quick walk down the street! "
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Unique oceanfront home with a deck, tons of natural light, & amazing views
Unique oceanfront home with a deck, tons of natural light, & amazing views
8.6 out of 10, Excellent, (49)
"Beautiful property. Saw seals from living room catching fish. Front door did not lock but it’s a safe neighborhood but a bit isolated. Kitchen is well equipped for cooking. Laundry facilities were a great help! Gorgeous views of the water and excellent service and communication."
Unique oceanfront home with a deck, tons of natural light, & amazing views
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.

Frequently asked questions

What can I expect from a resort vacation in Bailey Island?
You deserve some time off, and a resort is the ideal place to treat yourself to the amenities and services you need for a relaxing trip to Bailey Island. One of the comfortable resort hotels in the surrounding area could be just what you’re looking for, whether you’re hoping for a luxurious suite, shopping possibilities, or nightly entertainment options.
What's the best resort for my stay in Bailey Island?
Here are our top-rated resorts around Bailey Island: Once in a lifetime opportunity to rent the Chebeague Island Inn - 5.6 mi (8.9 km) from Bailey Island. Bates Island: Casco Bay Glamping Experience - 5.7 mi (9.1 km) from Bailey Island.
What can I do in Bailey Island?
Learn about the local history at monuments like Bailey Island Bridge, or bring the kids to Land’s End Gift Shop for some family fun. Additional attractions in the area include Ragged Island and Cobwork Bridge.
What's the seasonal weather like in Bailey Island?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Bailey Island are January, April, March, and February, with each month seeing an average of 9 inches of snowfall.
What's the best way to get to and around Bailey Island?
Fly into Portland Intl. Jetport Airport (PWM), which is located 17 mi (27.3 km) away from the heart of the city. You can also search for flights into Wiscasset, ME (ISS), which is 21.1 mi (33.9 km) away. If you’d like to venture out around the area, consider renting a car to take in more sights.