Title: Long Island Vacation Packages 2026 from $476 | 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 $476 ## 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. ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portland Harbor Hotel Downtown Portland $476 per person May 8 - May 10 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) 9.2/10 Wonderful! (1,668 reviews) Nice place, clean room, courteous staff, NO FREE PARKING! :( Reviewed on Feb 28, 2026 ![The Docent’s Collection – Thompson Block](https://images.trvl-media.com/lodging/39000000/38780000/38770100/38770068/e5025392_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Docent’s Collection – Thompson Block Downtown Portland $1,417 per person May 19 - May 26 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) 9.6/10 Exceptional! (249 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 ![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 $865 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Portland (PWM) 9.4/10 Exceptional! (1,001 reviews) Went for our honeymoon and fell in love with this place! Will definitely go back! Reviewed on Feb 26, 2026 ![Blind Tiger Portland - Danforth Street.](https://images.trvl-media.com/lodging/1000000/210000/200300/200246/4e66cf6e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Blind Tiger Portland - Danforth Street. West End Save 100% on your flight $848 per person May 21 - May 24 found 15 hours ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Portland (PWM) 9.6/10 Exceptional! (161 reviews) The whole was cozy! Well curated style and knowledgeable staff. Reviewed on Jan 5, 2026 ![The Weldon Hotel](https://images.trvl-media.com/lodging/108000000/107330000/107321700/107321604/38875013_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Weldon Hotel Downtown Portland $1,550 per person May 19 - May 26 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Portland (PWM) 9.8/10 Exceptional! (86 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 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/2026-04-01/2026-04-08/?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_6046209) ## Long Island Hotel Deals ![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/67608060_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 17 - Mar 18 Total with taxes and fees 8.8/10 Excellent! (1,003 reviews) Clean, quiet and comfortable. Exceptional team who were helpful and friendly. I actually hated to leave. Great stay! Reviewed on Feb 28, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F17%2F2026&endDate=3%2F18%2F2026&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true®ionId=6046209) ![Clarion Hotel Portland Airport ME](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/b163ad24_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 5 - Mar 6 Total with taxes and fees 8/10 Very Good! (1,380 reviews) Very clean and quiet. Optional breakfast which had very good portions. Only flaw i noticed was there were issues with the boiler. Hot water was scarce as they were at full capacity. Other than that i enjoyed my stay. Reviewed on Mar 1, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F5%2F2026&endDate=3%2F6%2F2026&selected=7171&PinnedHotelID=7171&HadPinnedHotel=true®ionId=6046209) ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_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 Mar 15 - Mar 16 Total with taxes and fees 9.2/10 Wonderful! (1,765 reviews) Nice place, clean room, courteous staff, NO FREE PARKING! :( Reviewed on Feb 28, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=898621&PinnedHotelID=898621&HadPinnedHotel=true®ionId=6046209) [See all 2,343 properties in Long Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F2%2F2026&endDate=3%2F3%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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