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Highland

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Highland Flights as Low as $180

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

Breeze Airways
Thu, Jun 11 - Wed, Jun 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$180 Roundtrip, found 4 days ago
$180
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jun 11 from Orlando Intl. to Stewart Intl., returning Wed, Jun 17, priced at $180 found 4 days ago
Breeze Airways
Thu, Jun 11 - Wed, Jun 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$183 Roundtrip, found 4 days ago
$183
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jun 11 from Orlando Intl. to Stewart Intl., returning Wed, Jun 17, priced at $183 found 4 days ago
Breeze Airways
Thu, Jun 11 - Wed, Jun 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$185 Roundtrip, found 4 days ago
$185
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jun 11 from Orlando Intl. to Stewart Intl., returning Wed, Jun 17, priced at $185 found 4 days ago
Breeze Airways
Thu, Jun 11 - Wed, Jun 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$190 Roundtrip, found 4 days ago
$190
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jun 11 from Orlando Intl. to Stewart Intl., returning Wed, Jun 17, priced at $190 found 4 days ago
Breeze Airways
Thu, Jun 11 - Wed, Jun 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$194 Roundtrip, found 4 days ago
$194
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jun 11 from Orlando Intl. to Stewart Intl., returning Wed, Jun 17, priced at $194 found 4 days ago
Breeze Airways
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$201 Roundtrip, found 4 days ago
$201
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $201 found 4 days ago
Breeze Airways
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$201 Roundtrip, found 5 days ago
$201
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $201 found 5 days ago
Breeze Airways
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$206 Roundtrip, found 2 days ago
$206
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $206 found 2 days ago
Breeze Airways
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$206 Roundtrip, found 5 days ago
$206
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $206 found 5 days ago
Breeze Airways
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$211 Roundtrip, found 5 days ago
$211
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $211 found 5 days ago
Breeze Airways
Wed, Jun 17 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$217 Roundtrip, found 4 days ago
$217
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Jun 17 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $217 found 4 days ago
Breeze Airways
Tue, Sep 1 - Sat, Sep 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$219 Roundtrip, found 1 hour ago
$219
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando Intl. to Stewart Intl., returning Sat, Sep 5, priced at $219 found 1 hour ago
Breeze Airways
Wed, Jun 17 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$222 Roundtrip, found 4 days ago
$222
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Jun 17 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $222 found 4 days ago
Breeze Airways
Tue, Sep 1 - Sat, Sep 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$224 Roundtrip, found 1 hour ago
$224
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando Intl. to Stewart Intl., returning Sat, Sep 5, priced at $224 found 1 hour ago
Breeze Airways
Wed, Jun 17 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$227 Roundtrip, found 4 days ago
$227
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Jun 17 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $227 found 4 days ago
Breeze Airways
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$228 Roundtrip, found 1 day ago
$228
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $228 found 1 day 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 $180, 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 $180 right now, why wait?

Highland Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$179

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 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 ...
7.8/10 Good! (1,004 reviews)
"No microwaves in rooms"

Reviewed on Jun 5, 2026

Get rates
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
Book a stay at this business-friendly hotel in Kingston. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
7.4/10 Good! (1,008 reviews)
"First Lady at the desk was rude and dismissive from the start and straight up walked away without saying anything. This then turned into a 25-30 minute wait with nobody at the front desk to assist. When the lady eventually came back, she had an even crappier attitude. The second guy (Kevin) was a ..."

Reviewed on Jun 1, 2026

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Best Western Plus Kingston Hotel And Conference Center
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Book a stay at this golf hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
8.2/10 Very Good! (120 reviews)
"The location is very good, near Fishkill and the highway but on a Friday night drivers without mufflers were making a lot of noise right up to midnight. It’s something they do regularly, I’m told. Also, the heater in our room was hard to regulate and a bit noisy. The breakfast was all right."

Reviewed on Jun 6, 2026

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Spark by Hilton Fishkill
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,012 reviews)
"Overall, I had a very nice and comfortable stay. Breakfast is good, but coffee is awful! The room is comfortable and clean, but marks on the wall/baseboard are not appealing along with rust spots in the shower. The chicken wings were delicious, and bar service on my last night was awesome! However, ..."

Reviewed on Jun 6, 2026

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Hyatt Place Poughkeepsie / Hudson Valley
Studio 6 Extended Stay Fishkill Route 9 NY

Studio 6 Extended Stay Fishkill Route 9 NY

2.5 out of 5
25 Merritt Blvd Fishkill NY
Stay at this hotel in Fishkill. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Van Wyck Homestead Museum and Fishkill Golf Course ...
6.6/10 (1,002 reviews)
"THANK YOU TO EVERYONE THAT WORK'S HERE JUST KNOW THAT YOU ALL ARE AMAZING THANK YOU"

Reviewed on Jun 1, 2026

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Studio 6 Extended Stay Fishkill Route 9 NY
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
2702 Main St Gardiner NY
Book a stay at this 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! (67 reviews)
"Amazing stay! Will be back"

Reviewed on May 16, 2026

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Wildflower Farms, Auberge Collection
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd Newburgh NY
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. ...
7.2/10 Good! (771 reviews)
"Stayed for one night with my family and the room was so clean and smelled good. So happy we found something that works for our future travel."

Reviewed on Jun 5, 2026

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The Crossroads Hotel, Newburgh
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz Poughkeepsie NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
8.6/10 Excellent! (1,008 reviews)
"Having broken AC and not offering a major discount is disgusting. Shame on management - they got guests into a bad position and frankly exploited them"

Reviewed on Jun 6, 2026

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DoubleTree by Hilton Poughkeepsie Convention Center
See all 1,559 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.