Title: Long Island Vacation Packages 2026 from $425 | 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 $425 ## 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. ![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 $425 per person Jun 2 - Jun 4 found 1 hour ago Roundtrip flight included Chicago (CHI) to Portland (PWM) 9/10 Wonderful! (1,000 reviews) The room was very clean! Reviewed on Oct 31, 2025 ![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 Save 100% on your flight $875 per person Jun 12 - Jun 15 found 21 hours ago Roundtrip non-stop flight included Chicago (CHI) to Portland (PWM) 9.6/10 Exceptional! (275 reviews) So spacious, decor is modern yet warm. Staff super friendly and helpful. Perfect location for concerts at Merrill, short walk. Reviewed on Mar 28, 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 Save 100% on your flight $863 per person Jun 12 - Jun 15 found 21 hours ago Roundtrip non-stop flight included Chicago (CHI) to Portland (PWM) 9.2/10 Wonderful! (1,776 reviews) We could have moved right in and been happy for life. Flawless. Reviewed on Mar 30, 2026 ![Blind Tiger Portland - Danforth Street.](https://images.trvl-media.com/lodging/1000000/210000/200300/200246/7a3d1c09_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Blind Tiger Portland - Danforth Street. West End Save 100% on your flight $1,006 per person Jun 12 - Jun 15 found 21 hours ago Roundtrip non-stop flight included Chicago (CHI) to Portland (PWM) 9.6/10 Exceptional! (175 reviews) The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend! Reviewed on Mar 10, 2026 ![Portland Regency Hotel & Spa](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/d87c36dc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portland Regency Hotel & Spa Downtown Portland $878 per person Jun 12 - Jun 15 found 21 hours ago Roundtrip non-stop flight included Chicago (CHI) to Portland (PWM) 9.4/10 Exceptional! (1,599 reviews) Clean spacious rooms, comfy beds good service Reviewed on Mar 29, 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/2026-04-30/2026-05-07/?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 $106 nightly $117 total Apr 16 - Apr 17 Total with taxes and fees 8.8/10 Excellent! (1,003 reviews) Breakfast was really good, free shuttle to town helped, the only problem was the bad was too small, but the rest was really good. Reviewed on Mar 29, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F16%2F2026&endDate=4%2F17%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! (1,408 reviews) The bad: Some towels were yellow, older carpets, 5th floor hallways with smells like people smoking in the room. Not sure if they have rooms where you can smoke. The good: They add some perfume seems to cover the odor. Everything else seems good. Place was good enough for the price. Plenty of ... Reviewed on Mar 29, 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 5 - Apr 6 Total with taxes and fees 9.2/10 Wonderful! (1,765 reviews) We could have moved right in and been happy for life. Flawless. Reviewed on Mar 30, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=898621&PinnedHotelID=898621&HadPinnedHotel=true®ionId=6046209) [See all 2,439 properties in Long Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F31%2F2026&endDate=4%2F1%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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