Title: Visit Bailey Island: Best of Bailey Island Tourism | Expedia Travel Guide - Expedia.ca [Hotels in Bailey Island](https://expedia.ca/Bailey-Island-Hotels.d6046825.Travel-Guide-Hotels)[Vacation Rentals in Bailey Island](https://expedia.ca/Bailey-Island-Vacation-Rentals.d6046825.Travel-Guide-VacationRentals)[Bailey Island Car Rentals](https://expedia.ca/Car-Rentals-In-Bailey-Island.d6046825.Car-Rental-Guide)[Bailey Island Vacation Packages](https://expedia.ca/Bailey-Island.d6046825.Destination-Travel-Guides) # Bailey Island ## Travel Guide ![Bailey Island featuring rugged coastline and a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/265000/265371-Bailey-Island-Maine.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Bailey Island which includes general coastal views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/265000/265181-Central-Coast-Maine.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Bailey Island showing general coastal views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/265000/265178-Central-Coast-Maine.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Bailey Island featuring signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/265000/265177-Central-Coast-Maine.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Bailey Island featuring a bay or harbour as well as an individual female](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/265000/265373-Bailey-Island-Maine.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Bailey Island Things to do #### Try to resist marooning yourself forever on this serene bit of land that features beaches, hikes and a lively community. Bailey Island is prototypical Maine, with rocky beaches, gruff lobster fishermen and small-town charm that epitomize the Pine Tree State. First settled by the son of a freed slave, William Black, the island is named after Reverend Thomas Bailey. Look down when driving over the Bailey Island Bridge to spot Will’s Gut, the spit separating Orr’s Island and Bailey Island and named for its original inhabitant. Pause at the opposite side of the bridge for a look at the bridge itself, a nationally recognized historic landmark, a rare cribstone bridge that allows the tides to pass through its structure. Drive to Mackerel Cove for the picture-postcard Maine settlement with small houses and lobster fishing boats bobbing on the edge of Casco Bay. Continue to the end of the island, Land’s End, and let the spray cool you down in the warmer months as you gaze across the sea. Buoys bobbing in the water indicate locations of lobster cages. Hike along the short Giant’s Stairs Trail to learn about the varied geology of Bailey Island. Climb down huge black stones, so different from surrounding rocks, and look for flecks of garnet and quartz. Bailey Island is part of Harpswell, with a town council governed by popular vote, creating a strong sense of community. Bailey Island’s community centre and main event space is the Bailey Island Library Hall. Stop by for an event or simply to see this historic building where the famous psychoanalyst Carl Jung gave an early American lecture. Drive to Bailey Island in 1 hour from Portland, Maine. Boat tours from Portland also occasionally come out to Harpswell and its more than 200 islands. Portland has an international airport serving numerous locations and is just 90 minutes by car from Boston. Harspwell does not have public transportation, so rent or bring a car. Bailey Island is the perfect place for a Maine getaway, whether you are locals, frequent visitors or have never been to this beautiful part of the world. - Bailey Island Hotel Deals - Vacation Rentals in Bailey Island ![New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach](https://images.trvl-media.com/lodging/28000000/27120000/27118300/27118287/c81a9afc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach Bailey Island ME Book a stay at this beach vacation home in Bailey Island. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Cobwork Bridge and Mackerel Cove ... 10/10 Exceptional! (212 reviews) Wonderful house. Well equipped. Gorgeous view. Reviewed on Nov 29, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=27118287&PinnedHotelID=27118287&HadPinnedHotel=true®ionId=6046825) [](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=27118287&PinnedHotelID=27118287&HadPinnedHotel=true®ionId=6046825) ![Tru by Hilton Portland Airport Area](https://images.trvl-media.com/lodging/19000000/18960000/18952900/18952854/c3cda57d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Tru by Hilton Portland Airport Area 369 Maine Mall Road South Portland ME CA $92 CA $100 total Jan 11 - Jan 12, 2026 includes taxes & fees Stay at this hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ... 8.8/10 Excellent! (1,646 reviews) The room was nice and the staff were very nice. Reviewed on Dec 8, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=18952854&PinnedHotelID=18952854&HadPinnedHotel=true®ionId=6046825) ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Portland Harbor Hotel 468 Fore Street Portland ME CA $147 CA $216 total Dec 23 - Dec 24 includes taxes & fees Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff ... 9.2/10 Wonderful! (1,712 reviews) Lovely stay in a beautiful room, appreciated the upgrade. Easy walk to downtown activities. Reviewed on Dec 12, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F12%2F2025&endDate=24%2F12%2F2025&selected=898621&PinnedHotelID=898621&HadPinnedHotel=true®ionId=6046825) [See all 1,777 properties in Bailey Island](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®ionId=6046825) 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. ![New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach](https://images.trvl-media.com/lodging/28000000/27120000/27118300/27118287/c81a9afc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach Bailey Island ME Book a stay at this beach vacation home in Bailey Island. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Cobwork Bridge and Mackerel Cove ... 10/10 Exceptional! (212 reviews) Wonderful house. Well equipped. Gorgeous view. Reviewed on Nov 29, 2025 [](https://expedia.ca/Bailey-Island-Hotels-New-Cottage-Perfect-For-A-Peaceful-And-Quiet-Stay-On-The-Ocean-With-Beach.h27118287.Hotel-Information) ![Nicest Waterfront in Maine w/ Private Beach!](https://images.trvl-media.com/lodging/69000000/68150000/68142400/68142325/w1771h1179x0y20-ab42fef4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Nicest Waterfront in Maine w/ Private Beach! Harpswell ME Book a stay at this beach vacation home in Bailey Island. Enjoy free WiFi, a beach locale, and a fitness center. Popular attractions Mackerel Cove and Land's ... 9.4/10 Exceptional! (44 reviews) We used this as the main stay place for our wedding weekend at the Johnson Field Preserve. It made the whole weekend fantastic and was a key piece. The location is fantastic and the layout/features of the house are very nice. A few things we thought need to be fixed and addressed:1\. The amenities ... Reviewed on Sep 9, 2025 [](https://expedia.ca/Bailey-Island-Hotels-Nicest-Waterfront-In-Maine-W-Private-Beach.h68142325.Hotel-Information) ![The Weldon Hotel](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/38875013_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Weldon Hotel 54 York St Portland ME Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Victoria Mansion and ... 9.8/10 Exceptional! (90 reviews) Hotel spotless and lovely. Service, when you could reach someone, was great. No front desk so you are a bit at the mercy of voicemail and remote assistance. Reviewed on Dec 14, 2025 [](https://expedia.ca/Portland-Hotels-The-Weldone-Hotel.h107321604.Hotel-Information) [See all properties in Bailey Island](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=6046825&sort=VACATION_RENTAL) 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. ## Check Bailey Island hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6046825&startDate=2025-12-16&endDate=2025-12-17)[Dec 16 - Dec 17](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6046825&startDate=2025-12-16&endDate=2025-12-17) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6046825&startDate=2025-12-17&endDate=2025-12-18)[Dec 17 - Dec 18](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6046825&startDate=2025-12-17&endDate=2025-12-18) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6046825&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025)[Dec 19 - Dec 21](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6046825&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6046825&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025)[Dec 26 - Dec 28](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6046825&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025) ### Popular places to visit #### 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. [](https://expedia.ca/Bailey-Island-Bridge-Bailey-Island.d6077256.Vacation-Attraction) #### 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. [](https://expedia.ca/Lands-End-Gift-Shop-Bailey-Island.d553248621532668102.Vacation-Attraction) #### 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. 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[Island Car Rentals Rental Cars in Casco Bay Islands ](https://www.expedia.ca/Island-Car-Rentals-Car-Rentals-In-Casco-Bay-Islands.d553248621532668098-c1132.Car-Rental-Guide-Suppliers) - [Kk Leisure Rental Cars in Casco Bay Islands ](https://www.expedia.ca/KK-Leisure-Car-Rentals-In-Casco-Bay-Islands.d553248621532668098-c1133.Car-Rental-Guide-Suppliers) - [National Car Rental Rental Cars in Great Island ](https://www.expedia.ca/National-Car-Rental-Car-Rentals-In-Great-Island.d553248635976193455-c42.Car-Rental-Guide-Suppliers) - [Thai Cars Rental Cars in Casco Bay Islands ](https://www.expedia.ca/Thai-Cars-Car-Rentals-In-Casco-Bay-Islands.d553248621532668098-c1027.Car-Rental-Guide-Suppliers) - [Great Island Vacation Rentals ](https://www.expedia.ca/Great-Island-Vacation-Rentals.d553248635976193455.Travel-Guide-VacationRentals) - [Things to do in Harpswell ](https://www.expedia.ca/Things-To-Do-In-Harpswell.d553248635077688915.Travel-Guide-Activities) - Cities near Bailey Island - Places of interest [Orrs Island](https://expedia.ca/Orrs-Island.dx3000440072)[Harpswell](https://expedia.ca/Harpswell.dx553248635077688915) - 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