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Highland

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Highland Flights as Low as $140

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

Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$140 Roundtrip, found 4 days ago
$140
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $140 found 4 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$143 Roundtrip, found 2 days ago
$143
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $143 found 2 days ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$145 Roundtrip, found 4 days ago
$145
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $145 found 4 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$146 Roundtrip, found 2 days ago
$146
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $146 found 2 days ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$150 Roundtrip, found 4 days ago
$150
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $150 found 4 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$153 Roundtrip, found 2 days ago
$153
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $153 found 2 days ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$155 Roundtrip, found 4 days ago
$155
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $155 found 4 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$156 Roundtrip, found 1 day ago
$156
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $156 found 1 day ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$157 Roundtrip, found 12 hours ago
$157
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $157 found 12 hours ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$160 Roundtrip, found 4 days ago
$160
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $160 found 4 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$161 Roundtrip, found 6 hours ago
$161
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $161 found 6 hours ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$162 Roundtrip, just found
$162
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $162 just found
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$165 Roundtrip, found 4 days ago
$165
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $165 found 4 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$166 Roundtrip, found 6 hours ago
$166
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $166 found 6 hours ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$168 Roundtrip, just found
$168
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $168 just found
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$173 Roundtrip, just found
$173
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $173 just found

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 May, 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 $140, 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 $140 right now, why wait?

Highland Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$139

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 5 to May 6
$106
includes taxes & fees
May 5 - May 6
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! (812 reviews)
"It was very clean. I was impressed by the staff. The lobby was spacious and welcoming. The room was spacious. The bed was okay, not the most comfortable but certainly acceptable."

Reviewed on Apr 10, 2025

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 $132 per night from Apr 20 to Apr 21
$132
includes taxes & fees
Apr 20 - Apr 21
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! (1,011 reviews)
"We had a good stay"

Reviewed on Apr 15, 2025

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 20 to Apr 21
$119
includes taxes & fees
Apr 20 - Apr 21
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! (1,005 reviews)
"Was there for the arm wrestling tournament"

Reviewed on Apr 12, 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 $163 per night from Apr 27 to Apr 28
$163
includes taxes & fees
Apr 27 - Apr 28
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! (298 reviews)
"Very nice, room was great, very spacious and clean. Staff was friendly and accommodating"

Reviewed on Apr 12, 2025

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
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 $117 per night from Apr 22 to Apr 23
$117
includes taxes & fees
Apr 22 - Apr 23
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! (1,004 reviews)
will stay again when in the area
"wonderful stay"

Reviewed on Apr 14, 2025

Best Western Plus Kingston Hotel And Conference Center
Wildflower Farms, Auberge Resorts Collection
Wildflower Farms, Auberge Resorts Collection
5 out of 5
2702 Main St, Gardiner, NY
The price is $1,014 per night from Apr 16 to Apr 17
$1,014
includes taxes & fees
Apr 16 - Apr 17
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! (49 reviews)
"Its a beautiful property and some of the best staff and service. Looking forward to be back soon"

Reviewed on Mar 4, 2025

Wildflower Farms, Auberge Resorts Collection
Thayer Hotel
Thayer Hotel
3.5 out of 5
674 Thayer Road, West Point, NY
The price is $287 per night from Apr 16 to Apr 17
$287
includes taxes & fees
Apr 16 - Apr 17
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! (529 reviews)
"It is so convenient to stay at when visiting West Point."

Reviewed on Apr 13, 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 $128 per night from Apr 20 to Apr 21
$128
includes taxes & fees
Apr 20 - Apr 21
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! (1,001 reviews)
"Helpful staff"

Reviewed on Apr 10, 2025

Hyatt Place Poughkeepsie / Hudson Valley
See all 1,496 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.