Search Cheap Flights to
Highland

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Highland Flights as Low as $122

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

Breeze Airways
Thu, May 1 - Sun, May 4
MCO
Orlando Intl.
SWF
Stewart Intl.
$122 Roundtrip, found 2 hours ago
$122
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, May 1 from Orlando Intl. to Stewart Intl., returning Sun, May 4, priced at $122 found 2 hours ago
Breeze Airways
Tue, Apr 1 - Tue, Apr 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$125 Roundtrip, found 3 days ago
$125
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Apr 1 from Orlando Intl. to Stewart Intl., returning Tue, Apr 8, priced at $125 found 3 days ago
Breeze Airways
Thu, May 1 - Sun, May 4
MCO
Orlando Intl.
SWF
Stewart Intl.
$127 Roundtrip, found 2 hours ago
$127
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, May 1 from Orlando Intl. to Stewart Intl., returning Sun, May 4, priced at $127 found 2 hours ago
Breeze Airways
Tue, Apr 1 - Tue, Apr 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$129 Roundtrip, found 3 days ago
$129
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Apr 1 from Orlando Intl. to Stewart Intl., returning Tue, Apr 8, priced at $129 found 3 days ago
Breeze Airways
Thu, May 1 - Sun, May 4
MCO
Orlando Intl.
SWF
Stewart Intl.
$132 Roundtrip, found 2 hours ago
$132
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, May 1 from Orlando Intl. to Stewart Intl., returning Sun, May 4, priced at $132 found 2 hours ago
Breeze Airways
Tue, Apr 1 - Tue, Apr 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$135 Roundtrip, found 3 days ago
$135
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Apr 1 from Orlando Intl. to Stewart Intl., returning Tue, Apr 8, priced at $135 found 3 days ago
Breeze Airways
Tue, Apr 1 - Tue, Apr 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$139 Roundtrip, found 6 hours ago
$139
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Tue, Apr 1 from Orlando Intl. to Stewart Intl., returning Tue, Apr 8, priced at $139 found 6 hours ago
Breeze Airways
Tue, Apr 1 - Tue, Apr 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$149 Roundtrip, found 6 hours ago
$149
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Tue, Apr 1 from Orlando Intl. to Stewart Intl., returning Tue, Apr 8, priced at $149 found 6 hours ago
Breeze Airways
Fri, Mar 28 - Mon, Mar 31
MCO
Orlando Intl.
SWF
Stewart Intl.
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Mar 28 from Orlando Intl. to Stewart Intl., returning Mon, Mar 31, priced at $159 found 2 days ago
Breeze Airways
Fri, Mar 28 - Sun, Mar 30
MCO
Orlando Intl.
SWF
Stewart Intl.
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Mar 28 from Orlando Intl. to Stewart Intl., returning Sun, Mar 30, priced at $159 found 2 days ago
Breeze Airways
Fri, Mar 28 - Mon, Mar 31
MCO
Orlando Intl.
SWF
Stewart Intl.
$162 Roundtrip, found 2 days ago
$162
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Mar 28 from Orlando Intl. to Stewart Intl., returning Mon, Mar 31, priced at $162 found 2 days ago
Breeze Airways
Fri, Mar 28 - Mon, Mar 31
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 2 days ago
$164
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Mar 28 from Orlando Intl. to Stewart Intl., returning Mon, Mar 31, priced at $164 found 2 days ago
Breeze Airways
Fri, Mar 28 - Mon, Mar 31
MCO
Orlando Intl.
SWF
Stewart Intl.
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Mar 28 from Orlando Intl. to Stewart Intl., returning Mon, Mar 31, priced at $167 found 2 days ago
Breeze Airways
Fri, Mar 28 - Mon, Mar 31
MCO
Orlando Intl.
SWF
Stewart Intl.
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Mar 28 from Orlando Intl. to Stewart Intl., returning Mon, Mar 31, priced at $169 found 2 days ago
Breeze Airways
Fri, Mar 28 - Sun, Mar 30
MCO
Orlando Intl.
SWF
Stewart Intl.
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Mar 28 from Orlando Intl. to Stewart Intl., returning Sun, Mar 30, priced at $169 found 2 days ago
Breeze Airways
Fri, Mar 28 - Mon, Mar 31
MCO
Orlando Intl.
SWF
Stewart Intl.
$172 Roundtrip, found 2 days ago
$172
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Mar 28 from Orlando Intl. to Stewart Intl., returning Mon, Mar 31, priced at $172 found 2 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 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 $122, 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 $122 right now, why wait?

Highland Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$121

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 $116 per night from Mar 31 to Apr 1
$116
includes taxes & fees
Mar 31 - Apr 1
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! (809 reviews)
"The property was great and clean from the moment you walk in you smell the freshness. Room was clean and was nice, we enjoy our stay here."

Reviewed on Mar 5, 2025

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
The price is $121 per night from Apr 6 to Apr 7
$121
includes taxes & fees
Apr 6 - Apr 7
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! (1,008 reviews)
"Nice experience"

Reviewed on Mar 21, 2025

HYATT house Fishkill/Poughkeepsie
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 Mar 26 to Mar 27
$137
includes taxes & fees
Mar 26 - Mar 27
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! (1,008 reviews)
"Very nice staff. Clean and well planned."

Reviewed on Mar 23, 2025

Hyatt Place Poughkeepsie / Hudson Valley
Wildflower Farms, Auberge Resorts Collection
Wildflower Farms, Auberge Resorts Collection
5 out of 5
2702 Main St, Gardiner, NY
The price is $738 per night from Mar 26 to Mar 27
$738
includes taxes & fees
Mar 26 - Mar 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! (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
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 $157 per night from Mar 26 to Mar 27
$157
includes taxes & fees
Mar 26 - Mar 27
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! (285 reviews)
"The Inn at Bellefield is a new property for over a year. The hotel is clean and stylish. The rooms/suites have a good flow of various spaces for various functions. It was a roomy studio for 2 people. It is located in a quiet area. However, there are new development plans for that area. The Inn at ..."

Reviewed on Mar 25, 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 $123 per night from Mar 30 to Mar 31
$123
includes taxes & fees
Mar 30 - Mar 31
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! (1,005 reviews)
Lovely stay
"Very clean, all employees were lovely. Parking was confusing at first with an event at the convention center, but the location ended up being very convenient"

Reviewed on Mar 24, 2025

DoubleTree by Hilton Poughkeepsie
Thayer Hotel
Thayer Hotel
3.5 out of 5
674 Thayer Road, West Point, NY
The price is $248 per night from Mar 30 to Mar 31
$248
includes taxes & fees
Mar 30 - Mar 31
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! (515 reviews)
"Wonderful stay"

Reviewed on Mar 14, 2025

Thayer Hotel
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 Mar 30 to Mar 31
$127
includes taxes & fees
Mar 30 - Mar 31
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)
Helpful staff
"Mariah was very helpful in locating my son’s favorite pillow"

Reviewed on Mar 23, 2025

Best Western Plus Kingston Hotel And Conference Center
See all 1,484 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.