Search Cheap Flights to
Highland

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Highland Flights as Low as $180

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

Breeze Airways
Thu, Aug 14 - Sun, Aug 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$180 Roundtrip, found 3 days ago
$180
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Aug 14 from Orlando Intl. to Stewart Intl., returning Sun, Aug 17, priced at $180 found 3 days ago
Breeze Airways
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$182 Roundtrip, found 2 days ago
$182
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jul 25 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $182 found 2 days ago
Breeze Airways
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$183 Roundtrip, found 3 days ago
$183
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Jul 25 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $183 found 3 days ago
Breeze Airways
Fri, Aug 1 - Sun, Aug 3
MCO
Orlando Intl.
SWF
Stewart Intl.
$186 Roundtrip, found 1 day ago
$186
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Stewart Intl., returning Sun, Aug 3, priced at $186 found 1 day ago
Breeze Airways
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$186 Roundtrip, found 3 days ago
$186
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Jul 25 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $186 found 3 days ago
Breeze Airways
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$188 Roundtrip, found 3 days ago
$188
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Jul 25 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $188 found 3 days ago
Breeze Airways
Thu, Jul 31 - Sun, Aug 3
MCO
Orlando Intl.
SWF
Stewart Intl.
$190 Roundtrip, found 4 hours ago
$190
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Thu, Jul 31 from Orlando Intl. to Stewart Intl., returning Sun, Aug 3, priced at $190 found 4 hours ago
Breeze Airways
Thu, Jul 24 - Tue, Jul 29
MCO
Orlando Intl.
SWF
Stewart Intl.
$190 Roundtrip, found 6 days ago
$190
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Jul 24 from Orlando Intl. to Stewart Intl., returning Tue, Jul 29, priced at $190 found 6 days ago
Breeze Airways
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$192 Roundtrip, found 2 days ago
$192
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jul 25 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $192 found 2 days ago
Breeze Airways
Fri, Aug 1 - Sun, Aug 3
MCO
Orlando Intl.
SWF
Stewart Intl.
$193 Roundtrip, found 4 days ago
$193
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Stewart Intl., returning Sun, Aug 3, priced at $193 found 4 days ago
Breeze Airways
Fri, Aug 1 - Sun, Aug 3
MCO
Orlando Intl.
SWF
Stewart Intl.
$194 Roundtrip, found 5 days ago
$194
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Stewart Intl., returning Sun, Aug 3, priced at $194 found 5 days ago
Breeze Airways
Fri, Aug 1 - Sun, Aug 3
MCO
Orlando Intl.
SWF
Stewart Intl.
$196 Roundtrip, found 1 day ago
$196
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Stewart Intl., returning Sun, Aug 3, priced at $196 found 1 day ago
Breeze Airways
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$196 Roundtrip, found 3 days ago
$196
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Jul 25 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $196 found 3 days ago
Breeze Airways
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$198 Roundtrip, found 4 days ago
$198
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jul 25 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $198 found 4 days ago
Breeze Airways
Thu, Jul 24 - Tue, Jul 29
MCO
Orlando Intl.
SWF
Stewart Intl.
$198 Roundtrip, found 2 days ago
$198
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jul 24 from Orlando Intl. to Stewart Intl., returning Tue, Jul 29, priced at $198 found 2 days ago
Fly Play
Sat, Jul 19 - Sat, Jul 26
CDG
Roissy-Charles de Gaulle
SWF
Stewart Intl.
$755 Roundtrip, found 3 days ago
$755
Roundtrip
found 3 days ago
Select Fly Play flight, departing Sat, Jul 19 from Roissy-Charles de Gaulle to Stewart Intl., returning Sat, Jul 26, priced at $755 found 3 days ago

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 August, 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 $180, 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 $180 right now, why wait?

Highland Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$179

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, I-87 Exit 18 to I-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! (837 reviews)
"The staff were very nice and friendly."

Reviewed on Jun 28, 2025

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SureStay Plus Hotel by Best Western Highland 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
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! (1,013 reviews)
"All the amenities in this hotel was great, as well as staff and cleanliness."

Reviewed on Jul 13, 2025

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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
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! (354 reviews)
"Great"

Reviewed on Jul 7, 2025

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Inn at Bellefield / Hyde Park, Residence Inn by Marriott
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
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! (1,006 reviews)
"Good service nice breakfast"

Reviewed on Jul 12, 2025

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HYATT house Fishkill/Poughkeepsie
Holiday Inn Express Poughkeepsie by IHG
Holiday Inn Express Poughkeepsie by IHG
2.5 out of 5
2750 South Road, Poughkeepsie, NY
Stay at this hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.6/10 Excellent! (1,004 reviews)
"We found this wonderful location to be just perfect!! Our check-in was a breeze, and the clerk was extremely accommodating. After a quiet night's rest we had the hotel's great hot breakfast. Plenty of free parking, right off a very convenient commercial corridor; I highly recommend this Holiday Inn, ..."

Reviewed on Jul 13, 2025

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Holiday Inn Express Poughkeepsie by IHG
Quality Inn Poughkeepsie
Quality Inn Poughkeepsie
2.5 out of 5
536 Haight Ave, Building A, Poughkeepsie, NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (368 reviews)
"Hotel was nicely situated to the walk way over the Hudson fireworks. Staff was very friendly. Suggestions-heat the pool. Also Room we were in was situated next to the stairwell. It was a little hard to sleep due to stairwell door slamming and people walking in stairwell throughout the evening. Would ..."

Reviewed on Jul 11, 2025

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Quality Inn Poughkeepsie
Quality Inn Hyde Park Poughkeepsie North
Quality Inn Hyde Park Poughkeepsie North
2.5 out of 5
4142 Albany Post Rd, 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 ...
8/10 Very Good! (1,010 reviews)
"the front entrance has a 6-8" step-up, this is NOT handicap accessible and VERY hard to use anything with wheels, wheel chairs, suitcases, luggage transporters, etc ..... so everything with wheels has to be rolled across about 3 feet of grass to get to the front door."

Reviewed on Jul 10, 2025

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Quality Inn Hyde Park Poughkeepsie North
Wingate by Wyndham Fishkill
Wingate by Wyndham Fishkill
3 out of 5
20 Schuyler Blvd, Fishkill, NY
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 ...
7.4/10 Good! (440 reviews)
"My room was like the picture."

Reviewed on Jul 11, 2025

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Wingate by Wyndham Fishkill
See all 1,528 properties in Highland
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.