Search Cheap Flights to
Highland

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Highland Flights as Low as $149

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

Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$149 Roundtrip, found 3 days ago
$149
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $149 found 3 days ago
Breeze Airways
Fri, Jun 13 - Sun, Jun 15
MCO
Orlando Intl.
SWF
Stewart Intl.
$150 Roundtrip, found 5 hours ago
$150
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Fri, Jun 13 from Orlando Intl. to Stewart Intl., returning Sun, Jun 15, priced at $150 found 5 hours ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$154 Roundtrip, found 3 days ago
$154
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $154 found 3 days ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$159 Roundtrip, found 3 days ago
$159
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $159 found 3 days ago
Breeze Airways
Fri, Jun 13 - Sun, Jun 15
MCO
Orlando Intl.
SWF
Stewart Intl.
$160 Roundtrip, found 5 hours ago
$160
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Fri, Jun 13 from Orlando Intl. to Stewart Intl., returning Sun, Jun 15, priced at $160 found 5 hours ago
Breeze Airways
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 3 days ago
$164
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jun 5 from Orlando Intl. to Stewart Intl., returning Sun, Jun 8, priced at $164 found 3 days ago
Breeze Airways
Mon, Dec 8 - Thu, Dec 11
MCO
Orlando Intl.
SWF
Stewart Intl.
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Dec 8 from Orlando Intl. to Stewart Intl., returning Thu, Dec 11, priced at $199 found 1 day ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$201 Roundtrip, found 2 hours ago
$201
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $201 found 2 hours ago
Breeze Airways
Mon, Dec 8 - Thu, Dec 11
MCO
Orlando Intl.
SWF
Stewart Intl.
$204 Roundtrip, found 1 day ago
$204
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Dec 8 from Orlando Intl. to Stewart Intl., returning Thu, Dec 11, priced at $204 found 1 day ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$206 Roundtrip, found 2 hours ago
$206
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $206 found 2 hours ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$211 Roundtrip, found 2 hours ago
$211
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $211 found 2 hours ago
Breeze Airways
Thu, Jun 19 - Mon, Jun 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$214 Roundtrip, found 11 hours ago
$214
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Mon, Jun 23, priced at $214 found 11 hours ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$217 Roundtrip, found 11 hours ago
$217
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $217 found 11 hours ago
Breeze Airways
Thu, Jun 19 - Mon, Jun 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$224 Roundtrip, found 11 hours ago
$224
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Mon, Jun 23, priced at $224 found 11 hours ago
Breeze Airways
Thu, Jun 19 - Sun, Jun 22
MCO
Orlando Intl.
SWF
Stewart Intl.
$251 Roundtrip, found 1 day ago
$251
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Sun, Jun 22, priced at $251 found 1 day ago
Fly Play
Wed, May 14 - Sun, May 18
AMS
Schiphol
SWF
Stewart Intl.
$420 Roundtrip, found 6 days ago
$420
Roundtrip
found 6 days ago
Select Fly Play flight, departing Wed, May 14 from Schiphol to Stewart Intl., returning Sun, May 18, priced at $420 found 6 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 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 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 $149, 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 $149 right now, why wait?

Highland Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$148

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! (822 reviews)
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Reviewed on May 4, 2025

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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
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! (1,011 reviews)
"Clean, efficient check in"

Reviewed on May 10, 2025

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HYATT house Fishkill/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! (1,005 reviews)
"It's a clean, well-run hotel with very reasonable rates. The desk staff are nice — I requested a quiet room and they gave me the quietest one in the building. There's a pool and a gym, and you can take a lovely walk on the rail trail right next door."

Reviewed on May 10, 2025

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Best Western Plus Kingston Hotel And Conference 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 ...
8.6/10 Excellent! (1,008 reviews)
"Clean. Front desk staff helpful and friendly"

Reviewed on May 9, 2025

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Hampton Inn & Suites Poughkeepsie
Beekman Arms Hotel
Beekman Arms Hotel
3.5 out of 5
6387 MILL ST, Rhinebeck, NY
Stay at this 3.5-star business-friendly inn in Rhinebeck. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.2/10 Very Good! (695 reviews)
"Staff was very friendly and accommodating, I had booked a room that I thought had fireplace but made a mistake and was a different room. The staff upgraded us to a room w fireplace without hesitation or extra fees. Stayed at many places before and it’s the little things that go a long way, plus Food ..."

Reviewed on May 8, 2025

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Beekman Arms Hotel
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! (323 reviews)
"Staff was helpful, facility was clean, and breakfast was very good."

Reviewed on May 9, 2025

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Inn at Bellefield / Hyde Park, Residence Inn by Marriott
Wildflower Farms, Auberge Resorts Collection
Wildflower Farms, Auberge Resorts Collection
5 out of 5
2702 Main St, Gardiner, NY
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! (50 reviews)
"Great stay"

Reviewed on Apr 21, 2025

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Wildflower Farms, Auberge Resorts Collection
DoubleTree by Hilton Poughkeepsie
DoubleTree by Hilton Poughkeepsie
4 out of 5
40 Civic Center Plz, Poughkeepsie, NY
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! (1,007 reviews)
"Great for conventions and easy access to train station."

Reviewed on May 6, 2025

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DoubleTree by Hilton Poughkeepsie
See all 1,499 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.