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Highland

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Highland Flights as Low as $117

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

Breeze Airways
Tue, Apr 1 - Mon, Apr 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$117 Roundtrip, found 6 days ago
$117
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Tue, Apr 1 from Orlando Intl. to Stewart Intl., returning Mon, Apr 7, priced at $117 found 6 days ago
Breeze Airways
Thu, Mar 6 - Mon, Mar 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$119 Roundtrip, found 2 days ago
$119
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Mar 6 from Orlando Intl. to Stewart Intl., returning Mon, Mar 10, priced at $119 found 2 days ago
Breeze Airways
Tue, Mar 25 - Sun, Mar 30
MCO
Orlando Intl.
SWF
Stewart Intl.
$122 Roundtrip, found 5 days ago
$122
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Tue, Mar 25 from Orlando Intl. to Stewart Intl., returning Sun, Mar 30, priced at $122 found 5 days ago
Breeze Airways
Thu, Feb 27 - Sun, Mar 2
MCO
Orlando Intl.
SWF
Stewart Intl.
$129 Roundtrip, found 6 days ago
$129
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Feb 27 from Orlando Intl. to Stewart Intl., returning Sun, Mar 2, priced at $129 found 6 days ago
Breeze Airways
Fri, Mar 14 - Sun, Mar 16
MCO
Orlando Intl.
SWF
Stewart Intl.
$158 Roundtrip, found 6 days ago
$158
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Mar 14 from Orlando Intl. to Stewart Intl., returning Sun, Mar 16, priced at $158 found 6 days ago
Breeze Airways
Fri, May 16 - Sun, May 18
MCO
Orlando Intl.
SWF
Stewart Intl.
$163 Roundtrip, found 2 days ago
$163
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, May 16 from Orlando Intl. to Stewart Intl., returning Sun, May 18, priced at $163 found 2 days ago
Breeze Airways
Fri, Mar 28 - Sun, Mar 30
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 1 day ago
$164
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Mar 28 from Orlando Intl. to Stewart Intl., returning Sun, Mar 30, priced at $164 found 1 day ago
Breeze Airways
Thu, Aug 28 - Tue, Sep 2
MCO
Orlando Intl.
SWF
Stewart Intl.
$173 Roundtrip, found 6 days ago
$173
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Aug 28 from Orlando Intl. to Stewart Intl., returning Tue, Sep 2, priced at $173 found 6 days ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$174 Roundtrip, found 1 day ago
$174
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $174 found 1 day ago
Breeze Airways
Fri, Feb 28 - Sun, Mar 2
MCO
Orlando Intl.
SWF
Stewart Intl.
$186 Roundtrip, found 5 days ago
$186
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Feb 28 from Orlando Intl. to Stewart Intl., returning Sun, Mar 2, priced at $186 found 5 days ago
Breeze Airways
Mon, Mar 31 - Sun, Apr 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$190 Roundtrip, found 6 days ago
$190
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Mon, Mar 31 from Orlando Intl. to Stewart Intl., returning Sun, Apr 6, priced at $190 found 6 days ago
Breeze Airways
Sun, Feb 23 - Mon, Feb 24
MCO
Orlando Intl.
SWF
Stewart Intl.
$438 Roundtrip, found 4 hours ago
$438
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Sun, Feb 23 from Orlando Intl. to Stewart Intl., returning Mon, Feb 24, priced at $438 found 4 hours ago
Breeze Airways
Sun, Feb 23 - Tue, Feb 25
MCO
Orlando Intl.
SWF
Stewart Intl.
$547 Roundtrip, found 4 days ago
$547
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sun, Feb 23 from Orlando Intl. to Stewart Intl., returning Tue, Feb 25, priced at $547 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 April, 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 13 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 $117, 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 $117 right now, why wait?

Highland Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$117

Last Minute Hotel Deals in Highland

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 $137 per night from Mar 16 to Mar 17
$137
includes taxes & fees
Mar 16 - Mar 17
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! (1,003 reviews)
"Could use a little updating, otherwise the stay was good."

Reviewed on Feb 21, 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 $117 per night from Mar 1 to Mar 2
$117
includes taxes & fees
Mar 1 - Mar 2
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)
"Had a good one day stay at HYATT Place Fishkill. Service counter people were friendly and welcoming. The room was spacious, clean and well appointed with amenities: microwave, fridge, coffee machine & suppliies. Breakfast served was good and plentiful. Good value!"

Reviewed on Feb 21, 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 Mar 16 to Mar 17
$163
includes taxes & fees
Mar 16 - Mar 17
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! (264 reviews)
"Lovely and convenient place to stay when visiting Hyde Park. My only complaint was our first night the people above us could be easily heard. Not sure if they were just loud or this is a design flaw."

Reviewed on Feb 18, 2025

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
The price is $849 per night from Mar 9 to Mar 10
$849
includes taxes & fees
Mar 9 - Mar 10
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! (46 reviews)
"Every aspect of this resort is top notch. We had a magical stay."

Reviewed on Feb 9, 2025

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 $123 per night from Mar 9 to Mar 10
$123
includes taxes & fees
Mar 9 - Mar 10
Book a 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 ...
9.4/10 Exceptional! (1,003 reviews)
Great for a stay to see colleges in the area
"Our stay was overnight after a college tour at SUNY New Paltz. The staff was friendly and answered any questions we had with a smile. The room was clean and very comfortable. It was also ver quiet."

Reviewed on Feb 19, 2025

Hampton Inn by Hilton New Paltz
Courtyard by Marriott Kingston
Courtyard by Marriott Kingston
3 out of 5
500 Frank Sottile Blvd, Kingston, NY
The price is $137 per night from Mar 9 to Mar 10
$137
includes taxes & fees
Mar 9 - Mar 10
Stay at this 3-star business-friendly hotel in Kingston. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.6/10 Excellent! (944 reviews)
"N"

Reviewed on Feb 21, 2025

Courtyard by Marriott Kingston
Hyatt Place Poughkeepsie / Hudson Valley
Hyatt Place Poughkeepsie / Hudson Valley
3 out of 5
2165 South Road, Poughkeepsie, NY
The price is $95 per night from Mar 25 to Mar 26
$95
includes taxes & fees
Mar 25 - Mar 26
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)
"Great location and staff was very accommodating."

Reviewed on Feb 20, 2025

Hyatt Place Poughkeepsie / Hudson Valley
Best Western Fishkill Inn & Suites
Best Western Fishkill Inn & Suites
3.5 out of 5
14 Schuyler Blvd, Fishkill, NY
The price is $108 per night from Mar 16 to Mar 17
$108
includes taxes & fees
Mar 16 - Mar 17
Book a stay at this 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! (769 reviews)
"Very friendly and accommodating staff!"

Reviewed on Feb 18, 2025

Best Western Fishkill Inn & Suites
See all 1,478 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.