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Highland

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Highland Flights as Low as $168

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

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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?

Highland Flight Information
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

SureStay Plus Hotel by Best Western Highland Poughkeepsie

2.5 out of 5
3423 US Highway 9W Highland NY
Book a stay at this business-friendly hotel in Highland. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
7.6/10 Good! (960 reviews)
Super clean! Hotel manager along with all other employees were pleasant and helpful.

Reviewed on Feb 6, 2026

SureStay Plus Hotel by Best Western Highland Poughkeepsie
Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
2641 South Road/Route 9 Poughkeepsie NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,015 reviews)
Property was cleared of snow quickly

Reviewed on Feb 10, 2026

Courtyard by Marriott Poughkeepsie
Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

3 out of 5
800 Frank Sottile Boulevard Kingston NY
Book a stay at this business-friendly hotel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (849 reviews)
Nice clear room, good breakfast.

Reviewed on Feb 13, 2026

Residence Inn by Marriott Kingston
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz Poughkeepsie NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
8.4/10 Very Good! (1,000 reviews)
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

DoubleTree by Hilton Poughkeepsie Convention Center
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd Poughkeepsie NY
Book a stay at this golf hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
8.8/10 Excellent! (1,003 reviews)
Room is awesome. Very large and comfortable

Reviewed on Feb 12, 2026

Hampton Inn & Suites Poughkeepsie
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
2702 Main St Gardiner NY
Book a stay at this luxury resort in Gardiner. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tuthilltown Spirits and DM Weil Gallery ...
9.4/10 Exceptional! (61 reviews)
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

Wildflower Farms, Auberge Collection
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

3 out of 5
25 OLD VINEYARD PLACE Hyde Park NY
Book a stay at this business-friendly hotel in Hyde Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.6/10 Exceptional! (468 reviews)
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

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
Hampton Inn Kingston

Hampton Inn Kingston

2.5 out of 5
1307 Ulster Ave Kingston NY
Book a stay at this business-friendly hotel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,001 reviews)
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

Hampton Inn Kingston
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.