Title: Chebeague Island Vacation Packages 2026 from $329 | Expedia.com [Chebeague Island Travel Guide](https://expedia.com/Chebeague-Island.dx6046986)[Hotels in Chebeague Island](https://expedia.com/Chebeague-Island-Hotels.d6046986.Travel-Guide-Hotels)[Vacation Rentals in Chebeague Island](https://expedia.com/Chebeague-Island-Vacation-Rentals.d6046986.Travel-Guide-VacationRentals)[Flights to Chebeague Island](https://expedia.com/Cheap-Flights-To-Chebeague-Island.d6046986.Travel-Guide-Flights)[Car Rentals in Chebeague Island](https://expedia.com/Car-Rentals-In-Chebeague-Island.d6046986.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chebeague Island Vacations from $329 ## 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 Chebeague Island Vacation Book a Chebeague Island vacation package that has only the things you need and nothing you don't. Good for festivals, markets and walking, consider staying in the neighborhood of Parkside. If a sightseeing tour is part of the program during your trip to Chebeague Island, check out major attractions like [Eagle Island](https://www.expedia.com/Eagle-Island-Maine.d6336768.Vacation-Attraction), [Little John Island Preserve](https://www.expedia.com/Little-John-Island-Preserve-Yarmouth.d553248621532668101.Vacation-Attraction) and [Sturdivant Island](https://www.expedia.com/Sturdivant-Island-Maine.d553248635976195124.Vacation-Attraction). That dream Chebeague Island vacation is a couple of clicks away. Browse hotels, flights and more on Expedia for an adventure that's tailored to suit your style. ## The Latest Chebeague Island vacation packages Price found within the past 48 hours. Click for updated prices. ![The McKernan Inn](https://images.trvl-media.com/lodging/106000000/105380000/105370700/105370688/1c19bdab_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The McKernan Inn $329 per person May 8 - May 10 found 4 hours ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Portland (PWM) 9.2/10 Wonderful! (91 reviews) Amazing experience. Beautiful view. Wonderful staff. Great experience! Reviewed on Mar 21, 2026 ![Ogunquit River Inn & Suites](https://images.trvl-media.com/lodging/2000000/1200000/1198100/1198069/6221f2a7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ogunquit River Inn & Suites $936 per person Jun 18 - Jun 22 found 1 day ago Roundtrip non-stop flight included Philadelphia (PHL) to Portland (PWM) 9/10 Wonderful! (1,000 reviews) The room was very clean! Reviewed on Oct 31, 2025 ![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 $852 per person May 10 - May 15 found 16 hours ago Roundtrip flight included Chicago (CHI) to Portland (PWM) 9.2/10 Wonderful! (1,776 reviews) Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great. Reviewed on Mar 24, 2026 ![Cape Arundel Inn and Resort](https://images.trvl-media.com/lodging/72000000/71810000/71807100/71807037/429c0f3c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cape Arundel Inn and Resort Save 100% on your flight $1,551 per person Jun 3 - Jun 9 found 8 hours ago Roundtrip non-stop flight included Phoenix (PHX) to Portland (PWM) 9.6/10 Exceptional! (42 reviews) Beautiful oceanfront Reviewed on Nov 12, 2025 ![USA Inn](https://images.trvl-media.com/lodging/13000000/12540000/12535100/12535042/e9711923_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### USA Inn $1,408 per person Jun 18 - Jun 22 found 1 day ago Roundtrip non-stop flight included Philadelphia (PHL) to Portland (PWM) 8/10 Very Good! (767 reviews) Parking was convenient. Staff was goo Reviewed on Nov 1, 2025 Don't see what you're looking for? See all available trips from Columbus to Chebeague Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-27/2026-05-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Chebeague 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 $106 nightly $117 total Apr 12 - Apr 13 Total with taxes and fees 8.8/10 Excellent! (1,001 reviews) I frequently stay at this property. It is a very clean property with kind and helpful staff and an excellent restaurant and spa. I was locked out of the next door parking garage and Dan (door man?) helped me get my car out. He ran out there in the freezing cold, called the garage mgmt and got me ... Reviewed on Mar 26, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true®ionId=6046986) ![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 refundable $77 nightly $85 total Apr 13 - Apr 14 Total with taxes and fees 8/10 Very Good! (1,401 reviews) Great rooms and nice staff Reviewed on Mar 26, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F13%2F2026&endDate=4%2F14%2F2026&selected=7171&PinnedHotelID=7171&HadPinnedHotel=true®ionId=6046986) ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/1a7f326f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Portland Harbor Hotel 468 Fore Street Portland ME Fully refundableReserve now, pay when you stay $161 nightly $178 total Apr 5 - Apr 6 Total with taxes and fees 9.2/10 Wonderful! (1,774 reviews) Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great. Reviewed on Mar 24, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=898621&PinnedHotelID=898621&HadPinnedHotel=true®ionId=6046986) [See all 2,270 properties in Chebeague Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F28%2F2026&endDate=3%2F29%2F2026®ionId=6046986) 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 Chebeague Island Vacation Packages ## Chebeague 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 | [State Theatre](https://www.expedia.com/State-Theatre-Downtown-Portland.d553248621532668181.Vacation-Attraction), [East End Beach](https://www.expedia.com/East-End-Beach-East-End.d6326357.Vacation-Attraction) and [Portland Museum of Art](https://www.expedia.com/Portland-Museum-Of-Art-Downtown-Portland.d6077214.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) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.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.com/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.com/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 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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 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![](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 Chebeague Island vacation package cost? ### What are the cheapest months to go to Chebeague Island? ### How many days is enough for Chebeague Island? ### How to find the best Chebeague Island package deals? ### Is it cheaper to book a Chebeague Island vacation as a package? ### When to book a vacation package to Chebeague Island? ### Does Expedia offer Book Now, Pay Later Chebeague Island vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Portland Hotels ](https://www.expedia.com/Portland-Hotels.d181420.Travel-Guide-Hotels) - [Casco Bay Islands Hotels ](https://www.expedia.com/Casco-Bay-Islands-Hotels.d553248621532668098.Travel-Guide-Hotels) - [Rv Parks in Casco Bay Islands ](https://www.expedia.com/Casco-Bay-Islands-RV-Parks.d553248621532668098-aaRVParks.Travel-Guide-Accommodation) - [B&B in Casco Bay Islands ](https://www.expedia.com/Casco-Bay-Islands-Bed-And-Breakfast.d553248621532668098-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Luxury Hotels in Casco Bay Islands ](https://www.expedia.com/Casco-Bay-Islands-Hotels-Luxury-Hotel.0-0-d553248621532668098-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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