Title: Bailey Island Vacation Packages & Trips 2026 | 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)[Bailey Island Car Rentals](https://expedia.ca/Car-Rentals-In-Bailey-Island.d6046825.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6046825/7787ff8e-ec8a-4628-8f3d-1af96a802dbe.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Bailey Island Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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 Plan, book, and manage your trip all in one place #### 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](https://www.expedia.ca/Bailey-Island-Bridge-Bailey-Island.d6077256.Vacation-Attraction), [Lands End Gift Shop](https://www.expedia.ca/Lands-End-Gift-Shop-Bailey-Island.d553248621532668102.Vacation-Attraction) and [Ragged Island](https://www.expedia.ca/Ragged-Island-Maine.d553248635976196478.Vacation-Attraction). A few quick clicks is all it takes to build a customized Bailey Island vacation on Expedia. ## Ready to book your vacation to Bailey Island? Choose your dates ## Bailey Island Hotel Deals ![Clarion Hotel Portland Airport ME](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/b163ad24_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Clarion Hotel Portland Airport ME 1230 Congress St Portland ME Fully refundableReserve now, pay when you stay CA $108 CA $120 total Jan 12 - Jan 13 includes taxes & fees 7.8/10 Good! (1,316 reviews) The staff were great. Friendly and helpful! Loved the use of the shuttle into town Reviewed on Jan 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F01%2F2026&endDate=13%2F01%2F2026&selected=7171&PinnedHotelID=7171&HadPinnedHotel=true®ionId=6046825) ![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/67608060_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Westin Portland Harborview 157 High St Portland ME Fully refundableReserve now, pay when you stay CA $136 CA $150 total Jan 26 - Jan 27 includes taxes & fees 8.8/10 Excellent! (1,008 reviews) Room was clean and had all amenities. Reviewed on Jan 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F01%2F2026&endDate=27%2F01%2F2026&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true®ionId=6046825) ![Portland Regency Hotel & Spa](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/c8a0ec33_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Portland Regency Hotel & Spa 20 Milk Street Portland ME Fully refundableReserve now, pay when you stay 9.4/10 Exceptional! (1,567 reviews) Staff was great. Perfect location to explore the area. Reviewed on Jan 4, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=24%2F01%2F2026&endDate=25%2F01%2F2026&selected=920050&PinnedHotelID=920050&HadPinnedHotel=true®ionId=6046825) [](https://expedia.ca/Hotel-Search?startDate=24%2F01%2F2026&endDate=25%2F01%2F2026&selected=920050&PinnedHotelID=920050&HadPinnedHotel=true®ionId=6046825) [See all 1,727 properties in Bailey Island](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F01%2F2026&endDate=12%2F01%2F2026®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 Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia - 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