Search Cheap Flights to
Highland

Photo by Karen Wirtz

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Highland Flights as Low as $122

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

Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways

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 January, 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 5 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 $122, 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 $122 right now, why wait?

Highland Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$121

Last Minute Hotel Deals in Highland

Rodeway Inn & Suites New Paltz - Hudson Valley
Rodeway Inn & Suites New Paltz - Hudson Valley
2 out of 5
601 Main Street, Highland, NY
The price is $90 per night from Dec 24 to Dec 25
$90
includes taxes & fees
Dec 24 - Dec 25
Stay at this motel in Highland. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.2/10 Good! (667 reviews)
"We had a very good experience. The only thing that made things a little difficult for us is that the bed in the room was very high off the floor. For shorter people, like my wife, that made getting into and out of bed harder than it should."

Reviewed on Nov 30, 2024

Rodeway Inn & Suites New Paltz - Hudson Valley
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, I-87 Exit 18 to I-9W, Highland, NY
The price is $116 per night from Dec 30 to Dec 31
$116
includes taxes & fees
Dec 30 - Dec 31
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! (798 reviews)
"The person at the front desk was very friendly and helpful."

Reviewed on Dec 6, 2024

SureStay Plus Hotel by Best Western Highland Poughkeepsie
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
The price is $111 per night from Jan 1 to Jan 2
$111
includes taxes & fees
Jan 1 - Jan 2, 2025
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,012 reviews)
"Comfortable and spacious rooms. Great nearby food options."

Reviewed on Dec 23, 2024

HYATT house Fishkill/Poughkeepsie
Best Western Fishkill Inn & Suites
Best Western Fishkill Inn & Suites
3.5 out of 5
14 Schuyler Blvd, Fishkill, NY
The price is $105 per night from Jan 1 to Jan 2
$105
includes taxes & fees
Jan 1 - Jan 2, 2025
Book a stay at this business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (715 reviews)
"Great staff"

Reviewed on Dec 22, 2024

Best Western Fishkill Inn & Suites
Wildflower Farms, Auberge Resorts Collection
Wildflower Farms, Auberge Resorts Collection
5 out of 5
2702 Main St, Gardiner, NY
The price is $1,050 per night from Jan 5 to Jan 6
$1,050
includes taxes & fees
Jan 5 - Jan 6, 2025
Stay at this 5-star luxury resort in Gardiner. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tuthilltown Spirits and DM Weil Gallery ...
9.2/10 Wonderful! (41 reviews)
"Beautiful place with stunning views - perfect place to unwind and relax. Food is amazing as well as friendly service."

Reviewed on Dec 16, 2024

Wildflower Farms, Auberge Resorts Collection
DoubleTree by Hilton Poughkeepsie
DoubleTree by Hilton Poughkeepsie
4 out of 5
40 Civic Center Plz, Poughkeepsie, NY
The price is $122 per night from Dec 30 to Dec 31
$122
includes taxes & fees
Dec 30 - Dec 31
Stay at this 4-star business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
8.2/10 Very Good! (1,001 reviews)
"Attentive staff. Alyse at the reception was very helpful!"

Reviewed on Dec 17, 2024

DoubleTree by Hilton Poughkeepsie
Best Western Plus Kingston Hotel And Conference Center
Best Western Plus Kingston Hotel And Conference Center
2.5 out of 5
503 Washington Ave, Kingston, NY
The price is $137 per night from Jan 1 to Jan 2
$137
includes taxes & fees
Jan 1 - Jan 2, 2025
Book a stay at this family-friendly hotel in Kingston. Enjoy free breakfast, free parking, and room service. Our guests praise the breakfast and the helpful ...
7.8/10 Good! (1,001 reviews)
"Staff was professional, accommodating and helpful with restaurant suggestions."

Reviewed on Dec 17, 2024

Best Western Plus Kingston Hotel And Conference Center
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
The price is $161 per night from Jan 15 to Jan 16
$161
includes taxes & fees
Jan 15 - Jan 16, 2025
Stay at this 3-star 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! (225 reviews)
"Brand new hotel, we really enjoyed our stay."

Reviewed on Dec 19, 2024

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
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.