Title: 5 Stars Hotels in Bailey Island, Maine from CA $101 - Find Cheap Bailey Island Hotels With 5 Stars | Expedia.ca [Bailey Island Travel Guide](https://expedia.ca/Bailey-Island.dx6046825)[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)[Flights to Bailey Island](https://expedia.ca/Cheap-Flights-To-Bailey-Island.d6046825.Travel-Guide-Flights)[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 featuring a bay or harbour](https://images.trvl-media.com/place/6046825/88defc19-9271-4674-8777-28e057b54db8.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6046825/88defc19-9271-4674-8777-28e057b54db8.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Bailey Island 5 Star Hotels Tonight [Jan 16 - Jan 17](https://www.expedia.ca/Hotel-Search?regionId=6046825&startDate=2026-01-16&endDate=2026-01-17&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 17 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6046825&startDate=2026-01-17&endDate=2026-01-18&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6046825&startDate=2026-01-16&endDate=2026-01-18&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6046825&startDate=2026-01-23&endDate=2026-01-25&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Bailey-Island-Hotels.s50-0-d6046825.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Bailey-Island-Hotels.s50-0-d6046825.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Bailey Island. ![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/67608060_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Westin Portland Harborview 157 High St Portland ME CA $136 CA $151 total Feb 1 - Feb 2 includes taxes & fees 8.8/10 Excellent! (1,004 reviews) [](https://expedia.ca/Portland-Hotels-The-Westin-Portland-Harborview.h6273.Hotel-Information) ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Portland Harbor Hotel 468 Fore Street Portland ME [Get rates](https://expedia.ca/Hotel-Search?startDate=31%2F01%2F2026&endDate=01%2F02%2F2026&selected=898621&PinnedHotelID=898621&HadPinnedHotel=true®ionId=6046825) 9.2/10 Wonderful! (1,755 reviews) [](https://expedia.ca/Portland-Hotels-Portland-Harbor-Hotel.h898621.Hotel-Information) ![DoubleTree by Hilton Hotel Portland](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/33bb60f2_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton Hotel Portland 363 Maine Mall Rd South Portland ME CA $93 CA $101 total Jan 25 - Jan 26 includes taxes & fees 8/10 Very Good! (1,325 reviews) [](https://expedia.ca/Portland-Hotels-DoubleTree-By-Hilton-Hotel-Portland.h8166.Hotel-Information) Still don't see what you're looking for? [See all properties in Bailey Island.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F01%2F2026&endDate=19%2F01%2F2026®ionId=6046825&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F01%2F2026&endDate=19%2F01%2F2026®ionId=6046825&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F01%2F2026&endDate=19%2F01%2F2026®ionId=6046825&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F01%2F2026&endDate=19%2F01%2F2026®ionId=6046825&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F01%2F2026&endDate=19%2F01%2F2026®ionId=6046825&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F01%2F2026&endDate=19%2F01%2F2026®ionId=6046825&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Bailey Island Hike the Giant's Stairs trail along the rocky coastline for dramatic views of Casco Bay. Seafood lovers shouldn't miss lobster rolls at Cook's Lobster & Ale House on the island's southern tip. [See all hotels in Bailey Island](https://www.expedia.ca/Hotel-Search?startDate=2026-01-31&endDate=2026-02-01&adults=2®ionId=6046825) ![Bailey Island showing general coastal views](https://images.trvl-media.com/place/6046825/3641ac6e-a5fc-4f22-a47d-0c23ea40681b.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Bailey Island Hotel Reviews ## Find out more about Bailey Island ## Five Star Hotels in Bailey Island There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Bailey Island so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Bailey Island and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Bailey Island Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Bailey Island The results are in, and Bailey Island 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Bailey Island! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Bailey Island today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Bailey Island? > - Search for the lowest price per night from CA $101 ### What makes a hotel 5 stars in Bailey Island? ### Are there any 5-star all-inclusive resorts in Bailey Island? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [2 Star Hotels in Acton ](https://www.expedia.ca/2Star-Acton-Hotels.s20-0-d3000421200.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Old Orchard Beach ](https://www.expedia.ca/2Star-Old-Orchard-Beach-Hotels.s20-0-d9256.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Portland ](https://www.expedia.ca/2Star-Portland-Hotels.s20-0-d181420.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Wells ](https://www.expedia.ca/2Star-Wells-Hotels.s20-0-d56045.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Limerick ](https://www.expedia.ca/3Star-Limerick-Hotels.s30-0-d3000439954.Travel-Guide-Filter-Hotels) - 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