Search Cheap Flights to
Highland

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Highland Flights as Low as $516

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

Fly Play
Fly Play
Fly Play
Fly Play
Fly Play
Fly Play

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.

Just the right flight

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.

Frequently Asked Questions About flights to Highland

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 June, 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 6 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 $516, 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 $516 right now, why wait?

Can I fly to Highland right now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to  right now?” When it’s time to book your flight, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

Highland Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$515

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 $72 per night from Mar 31 to Apr 1
$72
per night
Mar 31 - Apr 1
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. ...
6.8/10 (528 reviews)
Nice
"Nice room"

Reviewed on Mar 24, 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 $95 per night from Apr 4 to Apr 5
$95
per night
Apr 4 - Apr 5
Stay at this business-friendly hotel in Highland. Enjoy free breakfast, free parking, and WiFi. Our guests praise the helpful staff and the clean rooms in our ...
7.4/10 Good! (694 reviews)
"Nice staff"

Reviewed on Feb 17, 2024

SureStay Plus Hotel by Best Western Highland Poughkeepsie
DoubleTree by Hilton Poughkeepsie
DoubleTree by Hilton Poughkeepsie
4 out of 5
40 Civic Center Plz, Poughkeepsie, NY
The price is $117 per night from Mar 31 to Apr 1
$117
per night
Mar 31 - Apr 1
Stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast. Our guests praise the breakfast and the helpful staff in ...
8/10 Very Good! (911 reviews)
"Great property. Excellent staff. Clean room"

Reviewed on Mar 24, 2024

DoubleTree by Hilton Poughkeepsie
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
The price is $119 per night from Apr 7 to Apr 8
$119
per night
Apr 7 - Apr 8
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,010 reviews)
"Comfortable room, walk in shower, clean, welcoming, good breakfast, convenient location"

Reviewed on Mar 21, 2024

HYATT house Fishkill/Poughkeepsie
Hyatt Place Poughkeepsie / Hudson Valley
Hyatt Place Poughkeepsie / Hudson Valley
3 out of 5
2165 South Road, Poughkeepsie, NY
The price is $110 per night from Apr 4 to Apr 5
$110
per night
Apr 4 - Apr 5
Stay at this 3-star business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,014 reviews)
"Clean quiet with friendly staff"

Reviewed on Mar 23, 2024

Hyatt Place Poughkeepsie / Hudson Valley
Wildflower Farms, Auberge Resorts Collection
Wildflower Farms, Auberge Resorts Collection
5 out of 5
2702 Main St, Gardiner, NY
The price is $899 per night from Mar 31 to Apr 1
$899
per night
Mar 31 - Apr 1
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 ...
9.4/10 Exceptional! (14 reviews)
"Good environment view, but the room is just okay in consideration of the price."

Reviewed on Feb 25, 2024

Wildflower Farms, Auberge Resorts Collection
Hampton Inn by Hilton New Paltz
Hampton Inn by Hilton New Paltz
2.5 out of 5
4 South Putt Corners Road, New Paltz, NY
The price is $118 per night from Apr 4 to Apr 5
$118
per night
Apr 4 - Apr 5
Stay at this business-friendly hotel in New Paltz. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
9.4/10 Exceptional! (1,010 reviews)
Good, clean and pleasant hotel
"Pleasant place to stay, would come again when in the area. Near town with many restaurants. Sad that the fireplace in the lobby was out of order on a very rainy day. The indoor pool was quite nice. Breakfast ok. Stayed in a room with disabled accommodations, helpful though it would be good if such ..."

Reviewed on Mar 27, 2024

Hampton Inn by Hilton New Paltz
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 $135 per night from Apr 7 to Apr 8
$135
per night
Apr 7 - Apr 8
Stay at this 3-star business-friendly hotel in Hyde Park. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Richard L. Skimin Memorial Baseball ...
9.8/10 Exceptional! (46 reviews)
"Excellent hotel. Located right across from CIA, which was very convenient for us. The lobby is beautiful too. Very comfy bed! Would stay again."

Reviewed on Mar 25, 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.