Title: Bailey Island Holidays 2025 from $629 | Expedia.co.uk [Bailey Island Travel Guide](https://expedia.co.uk/Bailey-Island.dx6046825)[Hotels in Bailey Island](https://expedia.co.uk/Bailey-Island-Hotels.d6046825.Travel-Guide-Hotels)[Holiday Rentals in Bailey Island](https://expedia.co.uk/Bailey-Island-Holiday-Rentals.d6046825.Travel-Guide-HolidayRentals)[Bailey Island Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Bailey-Island.d6046825.Car-Hire-Guide) ![](https://images.trvl-media.com/place/6046825/7787ff8e-ec8a-4628-8f3d-1af96a802dbe.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Bailey Island Holidays from £655 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence ### Better together Save up to £335 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Packages with flights are ATOL protected #### 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](https://www.expedia.co.uk/Bailey-Island-Bridge-Bailey-Island.d6077256.Attraction), [Lands End Gift Shop](https://www.expedia.co.uk/Lands-End-Gift-Shop-Bailey-Island.d553248621532668102.Attraction) and [Ragged Island](https://www.expedia.co.uk/Ragged-Island-Maine.d553248635976196478.Attraction). A few quick clicks is all it takes to build a customised Bailey Island holiday on Expedia. ## Top Bailey Island Flight + Hotel Deals Price found within the past 48 hours. Click for updated prices. ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portland Harbor Hotel Downtown Portland £655 per person 8 Dec - 15 Dec found 1 day ago Return direct flight included London (LHR) to Portland (PWM) 9.2/10 Wonderful! (1,566 reviews) Wonderful! Great location!! Reviewed on 10 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-08/2025-12-15/?FromAirport=LHR&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=898621&paandie=true&dealMarker=-cYGHMTu509B0VrNLEmbUVZte3VBtkRAxL2EhPX_QdavSXF2mBIkzabPANMnbr6T) ![Hampton Inn Portland Downtown - Waterfront](https://images.trvl-media.com/lodging/5000000/4490000/4480300/4480291/1dc67cbc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn Portland Downtown - Waterfront Downtown Portland £677 per person 8 Dec - 15 Dec found 1 day ago Return direct flight included London (LHR) to Portland (PWM) 8.8/10 Excellent! (1,010 reviews) Great location for those on the go. It is close to the ferry, tour pickups, shopping, dining and very walkable. It was clean, front desk staff were helpful, and the free breakfast was very good - not something that can be said for a lot of hotels. Reasonably priced as well. Reviewed on 13 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-08/2025-12-15/?FromAirport=LHR&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=4480291&paandie=true&dealMarker=nrwrODVHqJn08yZIWkjtn6F_zYV3FBM7LaQnqCrXV3Z2thtuiEYcbF0jLuL2dgc8) ![Portland Regency Hotel & Spa](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/c8a0ec33_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portland Regency Hotel & Spa Downtown Portland £723 per person 8 Dec - 15 Dec found 1 day ago Return direct flight included London (LHR) to Portland (PWM) 9.4/10 Exceptional! (1,402 reviews) The staff was friendly and helpful. The front desk upgraded us to the governor’s suite, which was fabulous. The Armory Lounge in the hotel has great ambience, cocktails, and food. Maddie our server and bartender was excellent. We would definitely stay there again. Reviewed on 15 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-08/2025-12-15/?FromAirport=LHR&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=920050&paandie=true&dealMarker=nrwrODVHqJn08yZIWkjtn6F_zYV3FBM7LaQnqCrXV3brPGx1ZD5objX6mUrWUWFY) ![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/67608060_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Portland Harborview Downtown Portland £686 per person 8 Dec - 15 Dec found 1 day ago Return direct flight included London (LHR) to Portland (PWM) 8.8/10 Excellent! (1,006 reviews) Excellent staff and service Reviewed on 7 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-08/2025-12-15/?FromAirport=LHR&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6273&paandie=true&dealMarker=nrwrODVHqJn08yZIWkjtn6F_zYV3FBM7LaQnqCrXV3aK-GT-Ur999kuYw7W7Qm3Q) ![Inn By The Sea](https://images.trvl-media.com/lodging/2000000/1550000/1542800/1542725/d0fca35d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Inn By The Sea £1,044 per person 8 Dec - 15 Dec found 1 day ago Return direct flight included London (LHR) to Portland (PWM) 9.4/10 Exceptional! (280 reviews) Absolutely 5 star. Best bed I’ve slept in at a hotel bar none. Reviewed on 10 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-08/2025-12-15/?FromAirport=LHR&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1542725&paandie=true&dealMarker=nrwrODVHqJn08yZIWkjtn5D3IJECRl8TBSny3_dAYnk2-2VS-4YzR21mrtbUsRgJ) ## 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](https://www.expedia.co.uk/Thomas-Point-Beach-Brunswick.d6334491.Attraction), [Maine State Music Theatre](https://www.expedia.co.uk/Maine-State-Music-Theater-Brunswick.d6333877.Attraction) and [Sand Beach](https://www.expedia.co.uk/Sand-Beach-Portland.d553248621532668404.Attraction) | ## Top hotels in Bailey Island ![Fireside Inn & Suites Portland](https://images.trvl-media.com/lodging/1000000/10000/9900/9842/bc09b846_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Fireside Inn & Suites Portland 81 Riverside St, Portland, ME £101 24 Sept - 25 Sept includes taxes & fees 7.8/10 Good! (1,009 reviews) "Very pleased with our accommodations. A drive to Portland city center but convenient location just off the highway. Very clean, cool, and quiet. Staff was friendly and helpful." Reviewed on 9 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=24%2F09%2F2025&endDate=25%2F09%2F2025&selected=9842&PinnedHotelID=9842&HadPinnedHotel=true®ionId=6046825) ![Clarion Hotel Portland](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/b163ad24_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Clarion Hotel Portland 1230 Congress St, Portland, ME Fully refundableReserve now, pay when you stay £96 22 Sept - 23 Sept includes taxes & fees 7.8/10 Good! (1,050 reviews) "coffee in room was terrible and no coffee service in lobby. Couldn’t find anyplace to buy coffee to go." Reviewed on 9 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F09%2F2025&endDate=23%2F09%2F2025&selected=7171&PinnedHotelID=7171&HadPinnedHotel=true®ionId=6046825) ![La Quinta Inn & Suites by Wyndham Portland DT/Maine Med](https://images.trvl-media.com/lodging/1000000/30000/23500/23500/8325dcb5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Portland DT/Maine Med 340 Park Ave, Portland, ME Fully refundableReserve now, pay when you stay £139 22 Sept - 23 Sept includes taxes & fees 8.8/10 Excellent! (2,230 reviews) "The room is spacious. It has everything we need. The parking was costly at $10 but convenient." Reviewed on 5 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F09%2F2025&endDate=23%2F09%2F2025&selected=23500&PinnedHotelID=23500&HadPinnedHotel=true®ionId=6046825) [See all 1,792 properties in Bailey Island](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F09%2F2025&endDate=18%2F09%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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ### 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. 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