Title: Great Island Vacation Packages 2026 from $592 | Expedia.com [Great Island Travel Guide](https://expedia.com/Great-Island.dx553248635976193455)[Hotels in Great Island](https://expedia.com/Great-Island-Hotels.d553248635976193455.Travel-Guide-Hotels)[Vacation Rentals in Great Island](https://expedia.com/Great-Island-Vacation-Rentals.d553248635976193455.Travel-Guide-VacationRentals)[Flights to Great Island](https://expedia.com/Cheap-Flights-To-Great-Island.d553248635976193455.Travel-Guide-Flights)[Car Rentals in Great Island](https://expedia.com/Car-Rentals-In-Great-Island.d553248635976193455.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248635976193455/b810478a-1b10-4d3d-875c-106512d8fc7d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Great Island Vacations from $592 ## 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 ## The Latest Great Island vacation packages Price found within the past 48 hours. Click for updated prices. ![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 Save 100% on your flight $592 per person May 22 - May 25 found 4 hours ago Roundtrip flight included New York (JFK) 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/4000000/3990000/3981200/3981160/50b1cace_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cliff House Maine Bald Head Save 100% on your flight $828 per person Jun 19 - Jun 21 found 3 hours ago Roundtrip flight included Chicago (ORD) to Portland (PWM) 9.4/10 Exceptional! (1,002 reviews) The property is amazing and the staff were polite and very attentive. It’s a negative for me that I couldn’t take my 8 year old in the outdoor pool, but I’m sure if i wasn’t there with a child I’d appreciate a kid-free zone. The indoor pool was pretty filthy, with some wrappers and things floating in the water. The room service food was surprisingly just okay, with watery omelettes, minimalist potatoes for breakfast, a namesake pork sandwich that leaned toward a Cuban but took a left hand toward a crockpot pork. The chefs plate charcuterie was fine except for some form of pate that appeared as if the chef had chewed up some prosciutto , formed it into a rectangle, and pressed two pistachio bits it. I figured it for a nasty kitchen prank on the wealthy snobs paying $35 for a lunch able, so I left it behind. I can’t lie — the whole milk from a local farm that was supplied on each floor’s coffee bar was the best milk I’ve ever tasted in my life. I literally skipped the coffee and drank the milk by the glass, this cannot be overstated as trivial as it seems. Reviewed on Mar 31, 2026 ![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 $1,042 per person Jun 28 - Jul 2 found 1 day ago Roundtrip flight included Dallas (DFW) to Portland (PWM) 9.2/10 Wonderful! (93 reviews) Beachfront old building labelled "Hospitality" has the best view I have ever seen for breakfast. Watch seals and fishing boats pass by while eating (included with room) continental breakfast freshly prepared just for you. Super private, clean, and well maintained. Feels historic, beach and walking path outside front door. Campus location, has campus security and feels very safe. Kids loved playing on the oceanfront. Makes good base for seeing Portland, but is located in South Portland. Check out the lighthouses! Reviewed on Apr 7, 2026 ![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 $975 per person Jun 28 - Jul 2 found 1 day ago Roundtrip flight included Dallas (DFW) to Portland (PWM) 9.2/10 Wonderful! (1,766 reviews) We have really enjoyed our stay at Portland Harbor Hotel. Our room was clean, the location is super convenient, and the staff was super helpful with recommendations, especially Adam. Everywhere he recommended to check out was amazing! He was also very cheerful and welcoming daily. If we’re ever back in town visiting, we will definitely stay with your hotel again. Reviewed on Apr 8, 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 $1,164 per person May 14 - May 17 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) 9.6/10 Exceptional! (291 reviews) Beautiful space, clean room, friendly and accommodating staff, excellent location Reviewed on Apr 5, 2026 Don't see what you're looking for? See all available trips from Columbus to Great Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-09/2026-05-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Great 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) ## Great 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 $114 nightly $126 total Apr 26 - Apr 27 Total with taxes and fees 8.8/10 Excellent! (1,006 reviews) I chose this hotel specifically because it was advertised as pet-friendly, as I was traveling with my well-trained dog. While the location was convenient and the room itself was comfortable, the experience was soured by the lack of transparency regarding the pet policy. When I booked, the additional ... Reviewed on Apr 6, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F26%2F2026&endDate=4%2F27%2F2026&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true®ionId=553248635976193455) ![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 $126 nightly $139 total Apr 15 - Apr 16 Total with taxes and fees 9.4/10 Exceptional! (1,187 reviews) Clean, quiet, good stay. Reviewed on Apr 6, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F15%2F2026&endDate=4%2F16%2F2026&selected=77981687&PinnedHotelID=77981687&HadPinnedHotel=true®ionId=553248635976193455) ![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 $165 nightly $183 total Apr 12 - Apr 13 Total with taxes and fees 9.2/10 Wonderful! (1,764 reviews) We have really enjoyed our stay at Portland Harbor Hotel. Our room was clean, the location is super convenient, and the staff was super helpful with recommendations, especially Adam. Everywhere he recommended to check out was amazing! He was also very cheerful and welcoming daily. If we’re ever back ... Reviewed on Apr 8, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=898621&PinnedHotelID=898621&HadPinnedHotel=true®ionId=553248635976193455) [See all 2,098 properties in Great Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F10%2F2026&endDate=4%2F11%2F2026®ionId=553248635976193455) 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 Great Island Vacation Packages ## Great Island Essential Information | Language | English | | --------------- | ------------------------------------ | | Currency | U.S dollars | | Closest Airport | Portland Intl. Jetport Airport (PWM) | ## 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) 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