Title: Long Island Vacation Packages 2026 from $443 | Expedia.com [Long Island Travel Guide](https://expedia.com/Long-Island.dx6046209)[Hotels in Long Island](https://expedia.com/Long-Island-Hotels.d6046209.Travel-Guide-Hotels)[Vacation Rentals in Long Island](https://expedia.com/Long-Island-Vacation-Rentals.d6046209.Travel-Guide-VacationRentals)[Flights to Long Island](https://expedia.com/Cheap-Flights-To-Long-Island.d6046209.Travel-Guide-Flights)[Car Rentals in Long Island](https://expedia.com/Car-Rentals-In-Long-Island.d6046209.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6046209/390deb80-d9ac-4071-98a7-e1a415655ac7.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Long Island Vacations from $443 ## 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 Long Island Vacation An easy way to experience this vibrant city is with a custom-made Long Island vacation package. Stay in the neighborhood of Parkside, which is great for festivals, markets and walking or choose someplace else — our packages are all about you. [Sand Beach](https://www.expedia.com/Sand-Beach-Portland.d553248621532668404.Vacation-Attraction), [Fifth Maine Museum](https://www.expedia.com/Fifth-Maine-Museum-Peaks-Island.d6326227.Vacation-Attraction) and [Little Diamond Island](https://www.expedia.com/Little-Diamond-Island-Portland.d553248635975749337.Vacation-Attraction) are just some of the sights worth visiting during your trip to Long Island. Whoever you're going away with and whatever your bank balance, your dream Long Island vacation is just a few clicks away with Expedia. ## The Latest Long 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 $443 per person May 21 - May 24 found 1 day ago Roundtrip flight included New York (NYC) 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 $744 per person May 22 - May 25 found 1 day ago Roundtrip non-stop flight included Austin (AUS) to Portland (PWM) 9/10 Wonderful! (1,000 reviews) The room was very clean! Reviewed on Oct 31, 2025 ![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 $738 per person May 17 - May 20 found 23 hours ago Roundtrip flight included New York (LGA) to Portland (PWM) 9.4/10 Exceptional! (304 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 ![Dormir](https://images.trvl-media.com/lodging/10000000/9320000/9312400/9312400/eaaa6212_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Dormir $583 per person May 22 - May 25 found 1 day ago Roundtrip non-stop flight included Austin (AUS) to Portland (PWM) 8.8/10 Excellent! (999 reviews) Enjoyed my stay. Very reliable. Reviewed on Mar 20, 2026 ![The Wolfeboro Inn](https://images.trvl-media.com/lodging/2000000/1850000/1849000/1848958/ce903410_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wolfeboro Inn $880 per person Jun 12 - Jun 14 found 1 day ago Roundtrip flight included New York (JFK) to Portland (PWM) 8.2/10 Very Good! (560 reviews) We had a very nice room. We were given a free upgrade. Staff was very accommodating. Property is right in the center of town within walking distance of restaurants, shops, the lake and X-country skiing. We had a great time. Reviewed on Mar 1, 2026 Don't see what you're looking for? See all available trips from Columbus to Long Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-21/2026-04-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PWM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Long 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 Apr 12 - Apr 13 Total with taxes and fees 8.8/10 Excellent! (1,000 reviews) Beautiful room, clean shower Reviewed on Mar 17, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true®ionId=6046209) ![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! (1,400 reviews) Great, 4:30 am shuttle to Airport Reviewed on Mar 19, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F13%2F2026&endDate=4%2F14%2F2026&selected=7171&PinnedHotelID=7171&HadPinnedHotel=true®ionId=6046209) ![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 12 - Apr 13 Total with taxes and fees 9.2/10 Wonderful! (1,770 reviews) A very nice and unique hotel in a great location. Would definitely stay again. Reviewed on Mar 21, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=898621&PinnedHotelID=898621&HadPinnedHotel=true®ionId=6046209) [See all 2,430 properties in Long Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F22%2F2026&endDate=3%2F23%2F2026®ionId=6046209) 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 Long Island Vacation Packages ## Long Island Essential Information | Language | English | | --------------- | -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Portland Intl. Jetport Airport (PWM) | | Population | 210 | | Max Temp Winter | 30ºF | | Max Temp Summer | 70ºF | | Top Sights | [State Theatre](https://www.expedia.com/State-Theatre-Downtown-Portland.d553248621532668181.Vacation-Attraction), [Higgins Beach](https://www.expedia.com/Higgins-Beach-Maine.d6326755.Vacation-Attraction) and [East End Beach](https://www.expedia.com/East-End-Beach-East-End.d6326357.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 [](https://expedia.com/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.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in 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 Long Island vacation package cost? ### What are the cheapest months to go to Long Island? ### How many days is enough for Long Island? ### How to find the best Long Island package deals? ### Is it cheaper to book a Long Island vacation as a package? ### When to book a vacation package to Long Island? ### Does Expedia offer Book Now, Pay Later Long 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) - [Great Diamond Island Hotels ](https://www.expedia.com/Great-Diamond-Island-Hotels.d6342016.Travel-Guide-Hotels) - [Rv Parks in Great Diamond Island ](https://www.expedia.com/Great-Diamond-Island-RV-Parks.d6342016-aaRVParks.Travel-Guide-Accommodation) - [Golf Hotels in Great Diamond Island ](https://www.expedia.com/Great-Diamond-Island-Hotels-Golf-Hotel.0-0-d6342016-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hotels with Restaurants in Great Diamond Island ](https://www.expedia.com/Great-Diamond-Island-Hotels-Hotels-With-Restaurants.0-0-d6342016-tHotelswithRestaurants.Travel-Guide-Filter-Hotels) - [B&B in Great Diamond 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