Title: Bailey Island Vacation Packages 2026 from $780 | Expedia.com [Bailey Island Travel Guide](https://expedia.com/Bailey-Island.dx6046825)[Hotels in Bailey Island](https://expedia.com/Bailey-Island-Hotels.d6046825.Travel-Guide-Hotels)[Vacation Rentals in Bailey Island](https://expedia.com/Bailey-Island-Vacation-Rentals.d6046825.Travel-Guide-VacationRentals)[Flights to Bailey Island](https://expedia.com/Cheap-Flights-To-Bailey-Island.d6046825.Travel-Guide-Flights)[Car Rentals in Bailey Island](https://expedia.com/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 Vacations from $780 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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.com/Bailey-Island-Bridge-Bailey-Island.d6077256.Vacation-Attraction), [Lands End Gift Shop](https://www.expedia.com/Lands-End-Gift-Shop-Bailey-Island.d553248621532668102.Vacation-Attraction) and [Ragged Island](https://www.expedia.com/Ragged-Island-Maine.d553248635976196478.Vacation-Attraction). A few quick clicks is all it takes to build a customized Bailey Island vacation on Expedia. ## The Latest Bailey Island vacation packages Price found within the past 48 hours. Click for updated prices. ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/1a7f326f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portland Harbor Hotel Downtown Portland Save 100% on your flight $780 per person May 28 - Jun 1 found 1 day ago Roundtrip flight included Chicago (CHI) to Portland (PWM) 9.2/10 Wonderful! (1,765 reviews) Business facilities were perfect. Front desk man Roman was an all star helping us out. Whole stay was 100/100 Reviewed on Mar 4, 2026 ![The Weldon Hotel](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/9fd24e5f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Weldon Hotel Downtown Portland Save 100% on your flight $989 per person May 28 - Jun 1 found 1 day ago Roundtrip flight included Chicago (CHI) to Portland (PWM) 9.8/10 Exceptional! (93 reviews) Location is excellent. Short walking distance to every good restaurant and shop. The property was very nice and clean. The kitchen is very well equipped. The gym is very good sized for the size of the apartment building with 13 units in it. The management’s communication was prompt and friendly and responded to all of our wishes. However, the place is advertised as a hotel, but don’t expect services as in a hotel. It resembles more a short term rental home - no cleaning service and no lobby. Otherwise everything was very nice in the apartment and we had a great time. Reviewed on Jan 3, 2026 ![Blind Tiger Portland - Danforth Street.](https://images.trvl-media.com/lodging/1000000/210000/200300/200246/7a3d1c09_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Blind Tiger Portland - Danforth Street. West End Save 100% on your flight $1,001 per person May 28 - Jun 1 found 1 day ago Roundtrip flight included Chicago (CHI) to Portland (PWM) 9.6/10 Exceptional! (175 reviews) The whole was cozy! Well curated style and knowledgeable staff. Reviewed on Jan 5, 2026 ![Cliff House Maine](https://images.trvl-media.com/lodging/4000000/3990000/3981200/3981160/eb122fc0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cliff House Maine Bald Head Save 100% on your flight $1,161 per person May 7 - May 10 found 2 hours ago Roundtrip flight included Minneapolis (MSP) to Portland (PWM) 9.4/10 Exceptional! (1,001 reviews) Great hotel with super nice views! Reviewed on Mar 1, 2026 ![Inn By The Sea](https://images.trvl-media.com/lodging/2000000/1550000/1542800/1542725/a8100548_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Inn By The Sea Save 100% on your flight $1,079 per person May 28 - Jun 1 found 1 day ago Roundtrip flight included Chicago (CHI) to Portland (PWM) 9.4/10 Exceptional! (300 reviews) Such a beautiful place, great to walk on beach, nice view, staff great.. cozy place.. so well decorated.. highly recommend for a nice quiet get away Reviewed on Mar 4, 2026 Don't see what you're looking for? See all available trips from Columbus to Bailey Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-05/2026-04-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_6046825) ### Discover the most popular places to visit in Bailey Island #### Bailey Island Bridge 4.5/5(9 reviews) 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.com/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.com/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. [](https://expedia.com/Cobwork-Bridge-Bailey-Island.d553248621532668105.Vacation-Attraction) ## Bailey Island Hotel Deals ![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/c479d2b6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Westin Portland Harborview 157 High St Portland ME Fully refundableReserve now, pay when you stay $98 nightly $108 total Mar 22 - Mar 23 Total with taxes and fees 8.8/10 Excellent! (1,004 reviews) The room was very clean, check in and out was easy, parking was affordable. Reviewed on Mar 3, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true®ionId=6046825) ![Clarion Hotel Portland Airport ME](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/c90266f6_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 $77 nightly $85 total Mar 24 - Mar 25 Total with taxes and fees 8/10 Very Good! (1,392 reviews) Pros: Extremely comfortable bed. Pool and hot tub. 5 minute walk from the train and bus station with a free shuttle that also goes there and to the airport. Cons: Small and somewhat disappointing gym no free weights). Breakfast restaurant is basic and somewhat overpriced. There is noise when the ... Reviewed on Mar 5, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F24%2F2026&endDate=3%2F25%2F2026&selected=7171&PinnedHotelID=7171&HadPinnedHotel=true®ionId=6046825) ![Cambria Hotel Portland Downtown-Old Port](https://images.trvl-media.com/lodging/78000000/77990000/77981700/77981687/2540bb39_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cambria Hotel Portland Downtown-Old Port 25 HANCOCK STREET Portland ME Fully refundable $116 nightly $128 total Mar 22 - Mar 23 Total with taxes and fees 9.4/10 Exceptional! (1,168 reviews) Easy check in and friendly staff. Food was good room was big and with nice view. Reviewed on Mar 2, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=77981687&PinnedHotelID=77981687&HadPinnedHotel=true®ionId=6046825) [See all 1,782 properties in Bailey Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F6%2F2026&endDate=3%2F7%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. ## Find the Best Bailey Island Vacation Packages ## Bailey Island Essential Information | Language | English | | --------------- | ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Portland Intl. Jetport Airport (PWM) | | Max Temp Winter | 30ºF | | Max Temp Summer | 70ºF | | Top Sights | [Thomas Point Beach](https://www.expedia.com/Thomas-Point-Beach-Brunswick.d6334491.Vacation-Attraction), [Sand Beach](https://www.expedia.com/Sand-Beach-Portland.d553248621532668404.Vacation-Attraction) and [Wolfes Neck Woods State Park](https://www.expedia.com/Wolfes-Neck-Woods-State-Park-Freeport.d6190008.Vacation-Attraction) | ## More vacations you might like ![](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.com/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.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) 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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.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Bailey Island vacation package cost? ### What are the cheapest months to go to Bailey Island? ### How many days is enough for Bailey Island? ### Is it worth booking a vacation package to Bailey Island? ### How to find the best Bailey Island package deals? ### Is it cheaper to book a Bailey Island vacation as a package? ### When to book a vacation package to Bailey Island? ### Does Expedia offer Book Now, Pay Later Bailey Island vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [Hotels near Cobwork Bridge ](https://www.expedia.com/Cobwork-Bridge-Hotels.0-l553248621532668105-0.Travel-Guide-Filter-Hotels) - [Hotels near Land's End Gift Shop ](https://www.expedia.com/Lands-End-Gift-Shop-Hotels.0-l553248621532668102-0.Travel-Guide-Filter-Hotels) - [Hotels near Ash Cove Pottery ](https://www.expedia.com/Ash-Cove-Pottery-Hotels.0-l553248621532668104-0.Travel-Guide-Filter-Hotels) - [Hotels near Paddleworks ](https://www.expedia.com/Paddleworks-Hotels.0-l553248621532668107-0.Travel-Guide-Filter-Hotels) - [Hotels near West Harpswell 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