Search Cheap Flights to
Highland

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Highland Flights as Low as $164

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

Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 2 days ago
$164
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $164 found 2 days ago
Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $169 found 2 days ago
Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$174 Roundtrip, found 2 days ago
$174
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $174 found 2 days ago
Breeze Airways
Fri, May 9 - Mon, May 12
MCO
Orlando Intl.
SWF
Stewart Intl.
$181 Roundtrip, found 15 hours ago
$181
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Fri, May 9 from Orlando Intl. to Stewart Intl., returning Mon, May 12, priced at $181 found 15 hours ago
Breeze Airways
Fri, May 9 - Mon, May 12
MCO
Orlando Intl.
SWF
Stewart Intl.
$191 Roundtrip, found 15 hours ago
$191
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Fri, May 9 from Orlando Intl. to Stewart Intl., returning Mon, May 12, priced at $191 found 15 hours ago
Breeze Airways
Fri, Jun 6 - Mon, Jun 9
MCO
Orlando Intl.
SWF
Stewart Intl.
$195 Roundtrip, found 2 days ago
$195
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jun 6 from Orlando Intl. to Stewart Intl., returning Mon, Jun 9, priced at $195 found 2 days ago
Breeze Airways
Fri, Jun 6 - Mon, Jun 9
MCO
Orlando Intl.
SWF
Stewart Intl.
$200 Roundtrip, found 2 days ago
$200
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jun 6 from Orlando Intl. to Stewart Intl., returning Mon, Jun 9, priced at $200 found 2 days ago
Breeze Airways
Fri, Jun 6 - Mon, Jun 9
MCO
Orlando Intl.
SWF
Stewart Intl.
$205 Roundtrip, found 2 days ago
$205
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jun 6 from Orlando Intl. to Stewart Intl., returning Mon, Jun 9, priced at $205 found 2 days ago
Breeze Airways
Thu, Jun 19 - Mon, Jun 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$225 Roundtrip, found 4 days ago
$225
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Mon, Jun 23, priced at $225 found 4 days ago
Breeze Airways
Fri, Jun 20 - Tue, Jun 24
MCO
Orlando Intl.
SWF
Stewart Intl.
$230 Roundtrip, found 4 days ago
$230
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jun 20 from Orlando Intl. to Stewart Intl., returning Tue, Jun 24, priced at $230 found 4 days ago
Breeze Airways
Thu, Jun 26 - Sun, Jun 29
MCO
Orlando Intl.
SWF
Stewart Intl.
$231 Roundtrip, found 3 days ago
$231
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jun 26 from Orlando Intl. to Stewart Intl., returning Sun, Jun 29, priced at $231 found 3 days ago
Breeze Airways
Thu, Jun 19 - Mon, Jun 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$235 Roundtrip, found 4 days ago
$235
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Mon, Jun 23, priced at $235 found 4 days ago
Breeze Airways
Fri, Jun 20 - Tue, Jun 24
MCO
Orlando Intl.
SWF
Stewart Intl.
$240 Roundtrip, found 4 days ago
$240
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jun 20 from Orlando Intl. to Stewart Intl., returning Tue, Jun 24, priced at $240 found 4 days ago
Breeze Airways
Thu, Jun 26 - Sun, Jun 29
MCO
Orlando Intl.
SWF
Stewart Intl.
$241 Roundtrip, found 3 days ago
$241
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jun 26 from Orlando Intl. to Stewart Intl., returning Sun, Jun 29, priced at $241 found 3 days ago
Breeze Airways
Thu, May 22 - Mon, May 26
MCO
Orlando Intl.
SWF
Stewart Intl.
$245 Roundtrip, found 4 days ago
$245
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, May 22 from Orlando Intl. to Stewart Intl., returning Mon, May 26, priced at $245 found 4 days ago
Breeze Airways
Thu, Jun 12 - Mon, Jun 16
MCO
Orlando Intl.
SWF
Stewart Intl.
$251 Roundtrip, found 4 days ago
$251
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jun 12 from Orlando Intl. to Stewart Intl., returning Mon, Jun 16, priced at $251 found 4 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 $164, 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 $164 right now, why wait?

Highland Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$163

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
The price is $106 per night from May 8 to May 9
$106
includes taxes & fees
May 8 - May 9
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! (816 reviews)
"It was very clean and comfortable. Conveniently located to our planned activities."

Reviewed on Apr 27, 2025

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
The price is $127 per night from May 8 to May 9
$127
includes taxes & fees
May 8 - May 9
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! (1,000 reviews)
"it was a solid safe comfortable stay"

Reviewed on Apr 28, 2025

Best Western Plus Kingston Hotel And Conference Center
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
The price is $124 per night from May 11 to May 12
$124
includes taxes & fees
May 11 - May 12
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! (1,000 reviews)
"Super clean"

Reviewed on Apr 28, 2025

HYATT house Fishkill/Poughkeepsie
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 $182 per night from May 18 to May 19
$182
includes taxes & fees
May 18 - May 19
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! (315 reviews)
"Only a year old. Nice room. Great Staff."

Reviewed on Apr 28, 2025

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
DoubleTree by Hilton Poughkeepsie
DoubleTree by Hilton Poughkeepsie
4 out of 5
40 Civic Center Plz, Poughkeepsie, NY
The price is $138 per night from May 11 to May 12
$138
includes taxes & fees
May 11 - May 12
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)
"The Doubletree is an excellent option for anyone interested in staying in downtown Poughkeepsie. I have stayed there on three different occasions in the last three months, each time for several days,and have always had a good experience. The staff is friendly and welcoming, the parking is free, access ..."

Reviewed on Apr 27, 2025

DoubleTree by Hilton Poughkeepsie
Wildflower Farms, Auberge Resorts Collection
Wildflower Farms, Auberge Resorts Collection
5 out of 5
2702 Main St, Gardiner, NY
The price is $938 per night from May 26 to May 27
$938
includes taxes & fees
May 26 - May 27
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

Wildflower Farms, Auberge Resorts Collection
Thayer Hotel
Thayer Hotel
3.5 out of 5
674 Thayer Road, West Point, NY
The price is $282 per night from Jun 1 to Jun 2
$282
includes taxes & fees
Jun 1 - Jun 2
Stay at this 3.5-star business-friendly hotel in West Point. Enjoy free WiFi, room service, and a 24-hour front desk. Our guests praise the helpful staff and ...
8.8/10 Excellent! (537 reviews)
"The hotel and staff were overall excellent except for the female waitress on Saturday morning breakfast . The dinner waitress was outstanding. The Saturday morning hot buffet breafast food was not hot at all . It clearly was not worth the price and the service was terrible ."

Reviewed on Apr 24, 2025

Thayer Hotel
Hyatt Place Poughkeepsie / Hudson Valley
Hyatt Place Poughkeepsie / Hudson Valley
3 out of 5
2165 South Road, Poughkeepsie, NY
The price is $137 per night from Jun 2 to Jun 3
$137
includes taxes & fees
Jun 2 - Jun 3
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! (1,002 reviews)
"Great clean place to stay"

Reviewed on Apr 28, 2025

Hyatt Place Poughkeepsie / Hudson Valley
See all 1,493 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.