Title: Highland Vacation Packages 2026 from $369 | Expedia.com [Highland Travel Guide](https://expedia.com/Highland.dx115050)[Hotels in Highland](https://expedia.com/Highland-Hotels.d115050.Travel-Guide-Hotels)[Vacation Rentals in Highland](https://expedia.com/Highland-Vacation-Rentals.d115050.Travel-Guide-VacationRentals)[Flights to Highland](https://expedia.com/Cheap-Flights-To-Highland.d115050.Travel-Guide-Flights)[Things to do in Highland](https://expedia.com/Things-To-Do-In-Highland.d115050.Travel-Guide-Activities)[Car Rentals in Highland](https://expedia.com/Car-Rentals-In-Highland.d115050.Car-Rental-Guide) ![](https://images.trvl-media.com/place/115050/b32ec179-9506-4b41-93f2-d2bb1696fa06.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Highland Vacations from $369 ## 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 Highland Vacation Reserve a Highland vacation package and get set to experience all this city has to offer. Consider basing yourself in the neighborhood of Poughkeepsie Waterfront, which is great for families, history and culture. If sightseeing is on the to-do list during your trip to Highland, swing by well-known attractions like [Walkway Over the Hudson State Historic Park](https://www.expedia.com/Walkway-Over-The-Hudson-State-Historic-Park-New-York.d6222117.Vacation-Attraction), [Franklin D Roosevelt Library & Museum](https://www.expedia.com/Franklin-D-Roosevelt-Library-Museum-Highland.d553248621533116643.Vacation-Attraction) and [Apple Greens Golf Course](https://www.expedia.com/Apple-Greens-Golf-Course-Highland.d553248621559724941.Vacation-Attraction). Check out Expedia's wide range of travel options and book your dream vacation to Highland now. ## The Latest Highland vacation packages Price found within the past 48 hours. Click for updated prices. ![OYO Times Square](https://images.trvl-media.com/lodging/1000000/10000/6700/6697/b192d80d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### OYO Times Square Manhattan Save 100% on your flight $369 per person Apr 23 - Apr 27 found 1 day ago Roundtrip flight included Atlanta (ATL) to New York (JFK) 7.2/10 Good! (1,617 reviews) Easy process and great location. Room is good for you need for a stay while you’re in the city Reviewed on Feb 1, 2026 ![Topping Rose House](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/8b4b1f10_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Topping Rose House $543 per person Mar 8 - Mar 12 found 4 hours ago Roundtrip flight included Dallas (DFW) to New York (JFK) 9.2/10 Wonderful! (136 reviews) Great rooms, staff and food Reviewed on Sep 28, 2025 ![Hotel St. James](https://images.trvl-media.com/lodging/2000000/1150000/1144500/1144474/ecd19bcc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel St. James Manhattan $490 per person Apr 23 - Apr 27 found 1 day ago Roundtrip flight included Atlanta (ATL) to New York (JFK) 8.8/10 Excellent! (6,546 reviews) The room was spotless, and location was fantastic. This is a very old hotel which a lot of history. The microwave and ice is in the lobby. Reviewed on Feb 6, 2026 ![Hotel Riu Plaza Manhattan Times Square](https://images.trvl-media.com/lodging/61000000/60680000/60677500/60677495/0bd08347_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Manhattan Times Square Manhattan $677 per person Apr 23 - Apr 27 found 1 day ago Roundtrip flight included Atlanta (ATL) to New York (JFK) 9.2/10 Wonderful! (3,348 reviews) The staff was nice and the rooms were clean! Great place! Reviewed on Feb 6, 2026 ![Mountain Springs Lake Resort](https://images.trvl-media.com/lodging/34000000/33270000/33260600/33260524/3c4b3304_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Mountain Springs Lake Resort $413 per person Mar 15 - Mar 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 9.6/10 Exceptional! (234 reviews) The staff was friendly and helpful. They were great! Reviewed on Feb 2, 2026 Don't see what you're looking for? See all available trips from Columbus to Highland [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-06/2026-03-13/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=POU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Highland #### Franklin D Roosevelt Library & Museum You can study the exhibits at Franklin D Roosevelt Library & Museum, a museum with a story of its own, during your travels to Highland. While you're in the area, stroll along the riverfront. [](https://expedia.com/Franklin-D-Roosevelt-Library-Museum-Highland.d553248621533116643.Vacation-Attraction) ### What to do in Highland ![Bear Mountain State Park+ BeaconTown 1-Day Tour From NY](https://mediaim.expedia.com/localexpert/50302489/1ceb0837-f410-471c-80a4-908b6cbc0dd2.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Bear Mountain State Park+ BeaconTown 1-Day Tour From NY $94 per adult [](https://expedia.com/things-to-do/bear-mountain-state-park-beacontown-1-day-tour-from-ny.a50302489.activity-details) [See all activities in Highland](https://expedia.com/things-to-do/search?rid=115050) ## Highland Hotel Deals ![SureStay Plus Hotel by Best Western Highland Poughkeepsie](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/960f4844_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### SureStay Plus Hotel by Best Western Highland Poughkeepsie 3423 US Highway 9W Highland NY Fully refundableReserve now, pay when you stay $74 nightly $83 total Feb 12 - Feb 13 Total with taxes and fees 7.6/10 Good! (959 reviews) Super clean Reviewed on Jan 15, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F12%2F2026&endDate=2%2F13%2F2026&selected=918797&PinnedHotelID=918797&HadPinnedHotel=true®ionId=115050) ![Our home is perfect for relaxing and having lots of fun, with near by activity’s](https://images.trvl-media.com/lodging/97000000/96410000/96402700/96402683/w1267h816x1y0-efb023de_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Our home is perfect for relaxing and having lots of fun, with near by activity’s Highland NY 9.4/10 Exceptional! (11 reviews) Great place to stay! Communication was great, beds are SUPER comfortable and the separate heating/cooling in each room is nice. The living room doesn't have enough seeing for it to be the hangout spot, so lots of kitchen conversations :) The piano was a fun addition and we had some fun musical moments. ... Reviewed on Nov 25, 2025 [Get rates](https://expedia.com/Hotel-Search?startDate=2%2F20%2F2026&endDate=2%2F21%2F2026&selected=96402683&PinnedHotelID=96402683&HadPinnedHotel=true®ionId=115050) [](https://expedia.com/Hotel-Search?startDate=2%2F20%2F2026&endDate=2%2F21%2F2026&selected=96402683&PinnedHotelID=96402683&HadPinnedHotel=true®ionId=115050) ![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Courtyard by Marriott Poughkeepsie 2641 South Road/Route 9 Poughkeepsie NY Fully refundableReserve now, pay when you stay $105 nightly $119 total Feb 16 - Feb 17 Total with taxes and fees 8.8/10 Excellent! (1,010 reviews) Clean room Reviewed on Feb 5, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F16%2F2026&endDate=2%2F17%2F2026&selected=5910&PinnedHotelID=5910&HadPinnedHotel=true®ionId=115050) [See all 1,542 properties in Highland](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F7%2F2026&endDate=2%2F8%2F2026®ionId=115050) 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 Highland Vacation Packages ## Highland Essential Information | Language | English | | --------------- | -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Stewart Intl. Airport (SWF) | | Population | 5,600 | | Max Temp Winter | 35ºF | | Max Temp Summer | 80ºF | | Top Sights | [Robibero Winery](https://www.expedia.com/Robibero-Winery-New-Paltz.d553248621532664710.Vacation-Attraction), [Benmarl Vineyards and Winery](https://www.expedia.com/Benmarl-Vineyards-And-Winery-Marlboro.d553248621532664678.Vacation-Attraction) and [Adair Vineyards](https://www.expedia.com/Adair-Vineyards-New-Paltz.d553248621532664703.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 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[](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 Highland vacation package cost? ### What are the cheapest months to go to Highland? ### How many days is enough for Highland? ### Is it worth booking a vacation package to Highland? ### How to find the best Highland package deals? ### Is it cheaper to book a Highland vacation as a package? ### When to book a vacation package to Highland? ### How to plan a trip to Highland? > 1. Choose when to get away: Check your diary and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to vacation in Highland. > 2. Work out your budget: Ensure you have enough money to pay for everything from transportation and food to airfares and activities. Your accommodations will probably be the largest expense during your trip to Highland. > 3. Use our [trip planning tool](https://www.expedia.com/why/trip-planning) to discover Highland: Research every aspect of your trip to Highland with this handy planner. Invite friends or family to collaborate on a group trip, search for hotels or things to do and make bookings. > 4. Decide how many days away: Start by compiling a list of the attractions and activities you want to get to in Highland. Then, estimate how long you'll need at each, including any travel time. > 5. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Highland vacation package that brings all your bookings together. > 6. Add on experiences and excursions: Read our dedicated travel guide to find some incredible [things to do in Highland](https://www.expedia.com/Things-To-Do-In-Highland.d115050.Travel-Guide-Activities) in Highland. Book tickets or make reservations in advance to save time and avoid the stress of looking for activities once you arrive. ### Does Expedia offer Book Now, Pay Later Highland vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [Hotels near Walkway Over the Hudson State Historic Park ](https://www.expedia.com/Walkway-Over-The-Hudson-State-Historic-Park-Hotels.0-l6222117-0.Travel-Guide-Filter-Hotels) - [Poughkeepsie Hotels ](https://www.expedia.com/Poughkeepsie-Hotels.d6056317.Travel-Guide-Hotels) - [Hotels near Marist College ](https://www.expedia.com/Marist-College-Hotels.0-l6158002-0.Travel-Guide-Filter-Hotels) - [Hotels near Poughkeepsie Bridge ](https://www.expedia.com/Poughkeepsie-Bridge-Hotels.0-l6093751-0.Travel-Guide-Filter-Hotels) - [Hotels near Mid-Hudson Children's Museum ](https://www.expedia.com/Mid-Hudson-Childrens-Museum-Hotels.0-l6219979-0.Travel-Guide-Filter-Hotels) - [Hotels near Poughkeepsie Station ](https://www.expedia.com/Poughkeepsie-Station-Hotels.d6194605.Travel-Guide-Hotels) - 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