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
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 5 days ago
$164
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $164 found 5 days ago
Breeze Airways
Thu, Oct 9 - Mon, Oct 13
MCO
Orlando Intl.
SWF
Stewart Intl.
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Oct 9 from Orlando Intl. to Stewart Intl., returning Mon, Oct 13, priced at $169 found 2 days ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $179 found 2 days ago
Breeze Airways
Fri, Aug 15 - Sat, Aug 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$184 Roundtrip, found 2 days ago
$184
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Orlando Intl. to Stewart Intl., returning Sat, Aug 23, priced at $184 found 2 days ago
Breeze Airways
Fri, Aug 15 - Sat, Aug 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$188 Roundtrip, found 2 days ago
$188
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Orlando Intl. to Stewart Intl., returning Sat, Aug 23, priced at $188 found 2 days ago
Breeze Airways
Fri, Aug 15 - Sat, Aug 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$189 Roundtrip, found 2 days ago
$189
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Orlando Intl. to Stewart Intl., returning Sat, Aug 23, priced at $189 found 2 days ago
Breeze Airways
Fri, Aug 15 - Sat, Aug 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$189 Roundtrip, found 2 days ago
$189
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Orlando Intl. to Stewart Intl., returning Sat, Aug 23, priced at $189 found 2 days ago
Breeze Airways
Fri, Aug 8 - Sun, Aug 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$192 Roundtrip, found 5 days ago
$192
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Aug 8 from Orlando Intl. to Stewart Intl., returning Sun, Aug 10, priced at $192 found 5 days ago
Breeze Airways
Fri, Aug 8 - Sun, Aug 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Aug 8 from Orlando Intl. to Stewart Intl., returning Sun, Aug 10, priced at $197 found 5 days ago
Breeze Airways
Fri, Aug 15 - Sat, Aug 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$198 Roundtrip, found 2 days ago
$198
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Orlando Intl. to Stewart Intl., returning Sat, Aug 23, priced at $198 found 2 days ago
Breeze Airways
Fri, Aug 15 - Sat, Aug 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$209 Roundtrip, found 8 hours ago
$209
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Orlando Intl. to Stewart Intl., returning Sat, Aug 23, priced at $209 found 8 hours ago
Breeze Airways
Fri, Aug 15 - Sat, Aug 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$212 Roundtrip, found 8 hours ago
$212
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Orlando Intl. to Stewart Intl., returning Sat, Aug 23, priced at $212 found 8 hours ago
Breeze Airways
Fri, Aug 15 - Sun, Aug 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$218 Roundtrip, found 3 days ago
$218
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Orlando Intl. to Stewart Intl., returning Sun, Aug 17, priced at $218 found 3 days ago
Breeze Airways
Fri, Aug 15 - Sat, Aug 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$219 Roundtrip, found 8 hours ago
$219
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Orlando Intl. to Stewart Intl., returning Sat, Aug 23, priced at $219 found 8 hours ago
Breeze Airways
Fri, Aug 15 - Sun, Aug 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$221 Roundtrip, found 2 days ago
$221
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Orlando Intl. to Stewart Intl., returning Sun, Aug 17, priced at $221 found 2 days ago
Breeze Airways
Fri, Aug 15 - Sat, Aug 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$222 Roundtrip, found 8 hours ago
$222
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Orlando Intl. to Stewart Intl., returning Sat, Aug 23, priced at $222 found 8 hours 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 September, 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
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! (849 reviews)
"Ashley at the front desk was wonderful! Can't wait to come back here!!"

Reviewed on Jul 26, 2025

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SureStay Plus Hotel by Best Western Highland Poughkeepsie
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road, Poughkeepsie, NY
Stay at this hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.6/10 Excellent! (1,003 reviews)
"Easy access, cleanliness, excellent room. Very good breakfast."

Reviewed on Aug 1, 2025

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Holiday Inn Express Poughkeepsie by IHG
Wingate by Wyndham Fishkill

Wingate by Wyndham Fishkill

3 out of 5
20 Schuyler Blvd, 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 ...
7.4/10 Good! (458 reviews)
"Would go back"

Reviewed on Jul 30, 2025

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Wingate by Wyndham Fishkill
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! (1,001 reviews)
Nice hotel
"It was fine, the breakfast was good. They varied the options every day"

Reviewed on Jul 31, 2025

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Best Western Plus Kingston Hotel And Conference Center
Americas Best Value Inn New Paltz

Americas Best Value Inn New Paltz

2 out of 5
7 Terwilliger Ln, New Paltz, NY
Book a stay at this business-friendly motel in New Paltz. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,022 reviews)
"Reasonable rates convenient to all"

Reviewed on Jul 30, 2025

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Americas Best Value Inn New Paltz
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! (371 reviews)
"Loved this modern and clean hotel."

Reviewed on Aug 1, 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 Mohonk Lake and Tuthilltown Spirits are ...
9.4/10 Exceptional! (51 reviews)
"Such a dreamy escape. The staff is excellent, friendly, and always ready to help. The rooms are serene and comfortable. Amazing spa and spa staff. Restaurant is also top-notch"

Reviewed on May 15, 2025

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Wildflower Farms, Auberge Resorts Collection
Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A, Poughkeepsie, NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.6/10 Good! (386 reviews)
"Not bad. Staff was fine."

Reviewed on Jul 30, 2025

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Quality Inn Poughkeepsie
See all 1,525 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.