Search Cheap Flights toHighland
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Highland Flights as Low as $168
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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 April, 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 $168, 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 $168 right now, why wait?
Destination airport | Stewart Intl. |
|---|---|
Destination airport IATA code | SWF |
Roundtrip price | $167 |
Last Minute Hotel Deals in Highland
SureStay Plus Hotel by Best Western Highland Poughkeepsie
Super clean! Hotel manager along with all other employees were pleasant and helpful.
Reviewed on Feb 6, 2026
Courtyard by Marriott Poughkeepsie
Property was cleared of snow quickly
Reviewed on Feb 10, 2026
Residence Inn by Marriott Kingston
Nice clear room, good breakfast.
Reviewed on Feb 13, 2026
DoubleTree by Hilton Poughkeepsie Convention Center
Very, very nice hotel. We were checked in quickly by a wonderful front desk crew, especially Henry. The hotel itself is spotless, parking is free, it's literally steps away from the convention center which was nice considering we were there when it was quite cold. The rooms were perfect and clean. ...
Reviewed on Feb 9, 2026
Hampton Inn & Suites Poughkeepsie
Room is awesome. Very large and comfortable
Reviewed on Feb 12, 2026
Wildflower Farms, Auberge Collection
This is a beautiful property with a very attentive staff. We enjoyed a wonderful family Christmas trip. Hope to go back soon!
Reviewed on Dec 30, 2025
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
The staff is incredibly courteous and helpful. The room is immaculate. Every amenity and convenience is considered in making your stay a pleasure.
Reviewed on Feb 1, 2026
Hampton Inn Kingston
Excellent stay. Thank you. It was great and service was excellent. Great room... Whirlpool tub, breakfast top notch. Arrived before time and they gave me the business room to use ahead of time so I could keep working.
Reviewed on Feb 12, 2026
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