Title: Chebeague Island Vacation Packages 2026 from $521 | 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 $521 ## 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. ![84 Main ](https://images.trvl-media.com/lodging/8000000/7810000/7805200/7805164/f78a93a3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 84 Main $521 per person Apr 7 - Apr 10 found 18 hours ago Roundtrip flight included Washington (DCA) to Portland (PWM) 10/10 Exceptional! (52 reviews) Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities. Reviewed on Dec 29, 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 $717 per person May 18 - May 22 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) 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 Docent's Collection at 121 Middle Street](https://images.trvl-media.com/lodging/39000000/38780000/38770100/38770068/148140d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Docent's Collection at 121 Middle Street Downtown Portland $980 per person May 21 - May 24 found 22 hours ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) 9.6/10 Exceptional! (273 reviews) Check-in and check-out are a breeze, easy access to a city parking lot on the block (needed as there was a snow ban on parking when I visited!). In terms of the space itself - clean, well appointed, spacious. Honestly a treat to stay here! Reviewed on Feb 23, 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 $618 per person May 18 - May 22 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) 9/10 Wonderful! (1,000 reviews) The room was very clean! Reviewed on Oct 31, 2025 ![Cliff House Maine](https://images.trvl-media.com/lodging/4000000/3990000/3981200/3981160/fe5a854b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cliff House Maine Bald Head Save 100% on your flight $1,090 per person May 9 - May 12 found 1 day ago Roundtrip non-stop flight included Minneapolis (MSP) to Portland (PWM) 9.4/10 Exceptional! (1,005 reviews) Great hotel with super nice views! Reviewed on Mar 1, 2026 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/2026-04-07/2026-04-14/?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_6046986) ## 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 $98 nightly $108 total Mar 29 - Mar 30 Total with taxes and fees 8.8/10 Excellent! (1,005 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%2F29%2F2026&endDate=3%2F30%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 refundableReserve now, pay when you stay $77 nightly $85 total Mar 24 - Mar 25 Total with taxes and fees 8/10 Very Good! (1,397 reviews) Room was super quiet, affordable, and beds were very comfortable. Love the location and the ample free parking. Reviewed on Mar 7, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F24%2F2026&endDate=3%2F25%2F2026&selected=7171&PinnedHotelID=7171&HadPinnedHotel=true®ionId=6046986) ![Portland Regency Hotel & Spa](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/d87c36dc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Portland Regency Hotel & Spa 20 Milk Street Portland ME Fully refundableReserve now, pay when you stay $143 nightly $158 total Apr 6 - Apr 7 Total with taxes and fees 9.4/10 Exceptional! (1,592 reviews) The staff is always superb each and every time we've stayed at this hotel. Amazing service! Reviewed on Mar 6, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F6%2F2026&endDate=4%2F7%2F2026&selected=920050&PinnedHotelID=920050&HadPinnedHotel=true®ionId=6046986) [See all 2,263 properties in Chebeague Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F8%2F2026&endDate=3%2F9%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 [](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 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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