Title: Bailey Island Vacation Packages & Trips 2025/2026 from CA $811 | 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. ## Top Bailey Island Vacation 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 CA $811 per person Jan 15 - Jan 21 found 1 day ago Roundtrip flight included Vancouver (YVR) to Portland (PWM) 18.4/10 Exceptional! (1,668 reviews) Hotel is so centrally located, you can't beat it. The bar is welcoming and perfect to play cards near the fireplace. Have stayed here a couple times now, and it's the new favorite. Parking is convenient, but a bit pricey at $45/night - but worth the access. Staff are kind and accommodating, rooms are clean and updated. Reviewed on Nov 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-15/2026-01-21/?FromAirport=YVR&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=898621&paandie=true&dealMarker=X0HSVkQz9Bs0Y7N1M7op0lKmtoUcn3l7jDWHYtMo5UyNi0KfqPGtr7TG7268yhIz) ![The Docent’s Collection – Thompson Block](https://images.trvl-media.com/lodging/39000000/38780000/38770100/38770068/e5025392_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Docent’s Collection – Thompson Block Downtown Portland CA $919 per person Jan 15 - Jan 21 found 1 day ago Roundtrip flight included Vancouver (YVR) to Portland (PWM) 19.2/10 Exceptional! (249 reviews) This is in a great location and room was very spacious. Blind in bedroom was broken in down position so it was always dark in there. You are supposed to download an app that requires “always on” connection to Bluetooth to get in, but someone was available to give us card keys instead. Reviewed on Nov 16, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-15/2026-01-21/?FromAirport=YVR&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=38770068&paandie=true&dealMarker=kNmD1Ubh-wzDEc31r82sUE8OZNwskrzE9rsuMnXSA1ZEoxV7q4sawTqhegyFPDPt) ![Blind Tiger Portland - Danforth Street.](https://images.trvl-media.com/lodging/1000000/210000/200300/200246/4e66cf6e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Blind Tiger Portland - Danforth Street. West End CA $1,093 per person Jan 15 - Jan 21 found 1 day ago Roundtrip flight included Vancouver (YVR) to Portland (PWM) 19.2/10 Exceptional! (161 reviews) Wish they had a liquor license and could do a cocktail hour in addition to a breakfast service. Wish they had just a tad more breakfast options. Really wish they had a key pad and front door access! LOVED the fire places in every room. Property manager was lovely and friendly. Loved the snacks available and variety. Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-15/2026-01-21/?FromAirport=YVR&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=200246&paandie=true&dealMarker=X0HSVkQz9Bs0Y7N1M7op0hgbKIH7Z6eGN_y2cJxjvZDd8r6Dcy_59e7AxVvT8Rfz) ![The Docent's Collection - Boyd Block](https://images.trvl-media.com/lodging/119000000/118150000/118144500/118144410/e3aa4f38_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Docent's Collection - Boyd Block Downtown Portland CA $1,206 per person Jan 15 - Jan 21 found 1 day ago Roundtrip flight included Vancouver (YVR) to Portland (PWM) 20/10 Exceptional! (2 reviews) Really nice and clean new hotel! Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-15/2026-01-21/?FromAirport=YVR&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=118144410&paandie=true&dealMarker=X0HSVkQz9Bs0Y7N1M7op0pGjC3CJuMsUz_v4WNx-0xsCkwX_Zb_v1cxY2Rrc5jSN) ![Blind Tiger Portland – Carleton Street](https://images.trvl-media.com/lodging/13000000/12750000/12743300/12743204/ed6b0e15_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Blind Tiger Portland – Carleton Street West End CA $1,255 per person Jan 15 - Jan 21 found 1 day ago Roundtrip flight included Vancouver (YVR) to Portland (PWM) 19.2/10 Exceptional! (119 reviews) Adorable spot in Portland, great location, really cool concept. Felt like an upgraded vacation rental. You don’t have the whole place to yourself but it basically feels like it. Check in and everything was seamless. The local recommendations, games, and snacks were a nice touch. We loved plays scrabble and drinking wine in the parlor. We do wish some items were a bit nicer given the cost. The bathroom could've had nicer facilities (cheap toilet seat, low water pressure) our bed was a rickety. The breakfast delivered was a nice touch but the contents itself kinda fell flat, not as curated as the website made it seem. Overall we still enjoyed our stay and the concept, but the website may have upsold it a bit. Reviewed on Nov 11, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-15/2026-01-21/?FromAirport=YVR&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12743204&paandie=true&dealMarker=X0HSVkQz9Bs0Y7N1M7op0jfQ_OMPYsK2XVsHSCb--vhvJCeKrz3qqKAJwGQHD7iq) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=PKG_BF_PROMO_6046825) ## Ready to book your vacation to Bailey Island? Choose your dates ## Bailey Island Hotel Deals ![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 10/10 Exceptional! (210 reviews) Great hosts, peaceful place, house was great! Reviewed on Nov 20, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=05%2F12%2F2025&endDate=06%2F12%2F2025&selected=27118287&PinnedHotelID=27118287&HadPinnedHotel=true®ionId=6046825) [](https://expedia.ca/Hotel-Search?startDate=05%2F12%2F2025&endDate=06%2F12%2F2025&selected=27118287&PinnedHotelID=27118287&HadPinnedHotel=true®ionId=6046825) ![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 $116 CA $129 total Dec 16 - Dec 17 includes taxes & fees 7.8/10 Good! (1,245 reviews) Yes we loved room 511 with the pull out bed chair ! Reviewed on Nov 19, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F12%2F2025&endDate=17%2F12%2F2025&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 $138 CA $152 total Dec 7 - Dec 8 includes taxes & fees 8.8/10 Excellent! (1,000 reviews) Clean room. Staff corrected a booking issue promptly. Reviewed on Nov 9, 2025 [](https://expedia.ca/Hotel-Search?startDate=07%2F12%2F2025&endDate=08%2F12%2F2025&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true®ionId=6046825) [See all 1,772 properties in Bailey Island](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=22%2F11%2F2025&endDate=23%2F11%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 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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[Cousins Island Vacations](https://www.expedia.ca/Cousins-Island.d553248635976197109.Destination-Travel-Guides) - [Desert of Maine](https://www.expedia.ca/Desert-Of-Maine-Freeport.d6190010.Vacation-Attraction) - [Durham Vacations](https://www.expedia.ca/Durham.d177509.Destination-Travel-Guides) - [East End Beach](https://www.expedia.ca/East-End-Beach-East-End.d6326357.Vacation-Attraction) - [Freeport Vacations](https://www.expedia.ca/Freeport.d180773.Destination-Travel-Guides) - [Great Diamond Island Vacations](https://www.expedia.ca/Great-Diamond-Island.d6342016.Destination-Travel-Guides) - [Great Island Vacations](https://www.expedia.ca/Great-Island.d553248635976193455.Destination-Travel-Guides) - [Visit Harpswell](https://www.expedia.ca/Harpswell.dx553248635077688915) - [Hermit Island Vacations](https://www.expedia.ca/Hermit-Island.d6341836.Destination-Travel-Guides) - [Higgins Beach](https://www.expedia.ca/Higgins-Beach-Maine.d6326755.Vacation-Attraction) - [Hunnewell Beach](https://www.expedia.ca/Hunnewell-Beach-Phippsburg.d662958045699522560.Vacation-Attraction) - [Josephine Newman Audubon Sanctuary](https://www.expedia.ca/Josephine-Newman-Audubon-Sanctuary-Georgetown.d6334323.Vacation-Attraction) - [Ll Bean Flagship Store](https://www.expedia.ca/LL-Bean-Flagship-Store-Freeport.d6180409.Vacation-Attraction) - [Long Island Vacations](https://www.expedia.ca/Long-Island.d6046209.Destination-Travel-Guides) - [Maine Mall](https://www.expedia.ca/Maine-Mall-South-Portland.d6077232.Vacation-Attraction) - [Mclellan-Sweat Mansion](https://www.expedia.ca/McLellan-Sweat-Mansion-Downtown-Portland.d6327527.Vacation-Attraction) - [Visit Orrs Island](https://www.expedia.ca/Orrs-Island.dx3000440072) - [Popham Beach State Park](https://www.expedia.ca/Popham-Beach-State-Park-Phippsburg.d6324334.Vacation-Attraction) - [Portland Head Light](https://www.expedia.ca/Portland-Head-Light-Cape-Elizabeth.d6077212.Vacation-Attraction) - [Portland Museum of Art](https://www.expedia.ca/Portland-Museum-Of-Art-Downtown-Portland.d6077214.Vacation-Attraction) - [Portland Vacations](https://www.expedia.ca/Portland.d181420.Destination-Travel-Guides) - [Scarborough Beach State Park](https://www.expedia.ca/Scarborough-Beach-State-Park-Scarborough.d6327764.Vacation-Attraction) - [Scarborough Vacations](https://www.expedia.ca/Scarborough.d6809.Destination-Travel-Guides) - [South Portland Vacations](https://www.expedia.ca/South-Portland.d6769.Destination-Travel-Guides) - [State Theatre](https://www.expedia.ca/State-Theatre-Downtown-Portland.d553248621532668181.Vacation-Attraction) - [Westbrook Vacations](https://www.expedia.ca/Westbrook.d56049.Destination-Travel-Guides) - [Windham Vacations](https://www.expedia.ca/Windham.d10053.Destination-Travel-Guides) ### Cars - [Bidvest Rental Cars in Casco Bay Islands](https://www.expedia.ca/Bidvest-Car-Rentals-In-Casco-Bay-Islands.d553248621532668098-c1087.Car-Rental-Guide-Suppliers) - [Budget Rental Cars in Harpswell](https://www.expedia.ca/Budget-Car-Rentals-In-Harpswell.d553248635077688915-c39.Car-Rental-Guide-Suppliers) - [Car rental Chebeague Island](https://www.expedia.ca/Car-Rentals-In-Chebeague-Island.d6046986.Car-Rental-Guide) - [Hertz Rental Cars in Harpswell Center](https://www.expedia.ca/Hertz-Car-Rentals-In-Harpswell-Center.d553248635975848499-c40.Car-Rental-Guide-Suppliers) - [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) ### Vacation Rental - [Great Island Vacation Rentals](https://www.expedia.ca/Great-Island-Vacation-Rentals.d553248635976193455.Travel-Guide-VacationRentals) ### Other - [Things to do in Harpswell](https://www.expedia.ca/Things-To-Do-In-Harpswell.d553248635077688915.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)