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Highland Flights as Low as $183
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Cheap Flights to Highland
Fall in love at first flight with your vacation to Highland by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Highland on Hotwire, and you’ll be up, up, and on a getaway in no time.
Because once the wheels are down in Highland, the good times start rolling. So buckle up, you’re in for a fun ride.
Frequently Asked Questions About flights to Highland
Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Highland with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.
So all you have to worry about is where you’re headed after the POU airport.
What is the cheapest month to fly to Highland?
Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Highland are in December, but when you book your flight on Hotwire, savings are always in season.
How many airlines fly to Highland?
Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Highland.
What airport is best to fly into Highland?
When you’re planning your trip to Highland, convenience is the name of the game. Luckily, Highland Stewart Intl. Airport is nearby so you can deplane and get going on checking off everything on your Highland must-do list.
How much are flights to Highland?
Got very cheap flights on your vacation itinerary? When you book your airline tickets to Highland on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $183, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.
How to get cheap flights to Highland?
The trick to saving a stack of cash on your flight to Highland? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $183 right now, why wait?
Destination airport | Stewart Intl. |
|---|---|
Destination airport IATA code | SWF |
Roundtrip price | $183 |
Last Minute Hotel Deals in Highland
SureStay Plus Hotel by Best Western Highland Poughkeepsie
Very clean and modern hotel for the price. Safe area, very comfortable beds, large rooms. Stayed here before and forgot, when we pulled up we were excited. We remembered how great it was! Definitely would stay again. Not far from New Paltz so a great choice if closer hotels are booked. Worth the ...
Reviewed on Nov 14, 2025
Best Western Plus Kingston Hotel And Conference Center
The room was great—clean. The restaurant was great—the food was tasty. The staff was exemplary. I would definitely stay here again.
Reviewed on Nov 11, 2025
Hampton Inn & Suites Poughkeepsie
Easy che kin nice, newly refurbished rooms.
Reviewed on Nov 13, 2025
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Never stayed at a Red Roof before. I was pleasantly surprise. Had a good night sleep and hot shower. The people at the front desk were very helpful and friendly.
Reviewed on Nov 13, 2025
Wildflower Farms, Auberge Collection
Where do I start…. Everything was clean and felt so luxurious. The staff was unbelievably polite, kind, and caring. The grounds are beautiful. The spa is perfect. The amenities are top tier. The food is TRULY farm to table (you can go see the farm on a 5 minute walk if you need proof). Just the perfect ...
Reviewed on Sep 16, 2025
Hyatt Place Poughkeepsie / Hudson Valley
Rooms were spacious and comfortable. You only get 3 small pillows which I thought was strange. They had an onsite bar with bar style food that was decent. Would stay here again.
Reviewed on Nov 10, 2025
Hampton Inn by Hilton New Paltz
Rooms were clean and comfortable, breakfast was good for everyone
Reviewed on Nov 12, 2025
Minnewaska Lodge
Maggie is a delightful innkeeper and host. Very kind and welcoming. My wife and i will be back.
Reviewed on Nov 12, 2025
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