Search Cheap Flights to
Highland

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Highland Flights as Low as $119

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

Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Stewart Intl., returning Sun, Sep 7, priced at $119 found 1 day ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$124 Roundtrip, found 1 day ago
$124
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Stewart Intl., returning Sun, Sep 7, priced at $124 found 1 day ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$127 Roundtrip, found 4 days ago
$127
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Stewart Intl., returning Sun, Sep 7, priced at $127 found 4 days ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$130 Roundtrip, found 1 day ago
$130
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Stewart Intl., returning Sun, Sep 7, priced at $130 found 1 day ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$131 Roundtrip, found 3 days ago
$131
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Stewart Intl., returning Sun, Sep 7, priced at $131 found 3 days ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$136 Roundtrip, found 3 days ago
$136
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Stewart Intl., returning Sun, Sep 7, priced at $136 found 3 days ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$137 Roundtrip, found 4 days ago
$137
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Stewart Intl., returning Sun, Sep 7, priced at $137 found 4 days ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$141 Roundtrip, found 3 days ago
$141
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Stewart Intl., returning Sun, Sep 7, priced at $141 found 3 days ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 2 days ago
$164
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 $164 found 2 days ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$169 Roundtrip, found 2 days ago
$169
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 $169 found 2 days ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$174 Roundtrip, found 2 days ago
$174
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 $174 found 2 days ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$180 Roundtrip, found 2 days ago
$180
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 $180 found 2 days ago
Breeze Airways
Tue, Aug 19 - Thu, Aug 21
MCO
Orlando Intl.
SWF
Stewart Intl.
$180 Roundtrip, found 6 days ago
$180
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Tue, Aug 19 from Orlando Intl. to Stewart Intl., returning Thu, Aug 21, priced at $180 found 6 days ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$185 Roundtrip, found 2 days ago
$185
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 $185 found 2 days ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$233 Roundtrip, found 5 days ago
$233
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $233 found 5 days ago
Breeze Airways
Fri, Nov 21 - Fri, Nov 28
RSW
Southwest Florida Intl.
SWF
Stewart Intl.
$747 Roundtrip, found 1 day ago
$747
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Nov 21 from Southwest Florida Intl. to Stewart Intl., returning Fri, Nov 28, priced at $747 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 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 $119, 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 $119 right now, why wait?

Highland Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$118

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! (855 reviews)
"The staff was super friendly"

Reviewed on Aug 10, 2025

Get rates
SureStay Plus Hotel by Best Western Highland Poughkeepsie
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
Stay at this 3-star 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! (510 reviews)
"Comfortable place to stay"

Reviewed on Aug 7, 2025

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The Crossroads Hotel, Newburgh
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
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! (472 reviews)
"Beautiful renovated hotel. We loved our stay here"

Reviewed on Aug 10, 2025

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Wingate by Wyndham Fishkill
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! (1,002 reviews)
"The bathroom needed some work. The edges and corners have a lot of dirt build up"

Reviewed on Aug 3, 2025

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Holiday Inn Express Poughkeepsie by IHG
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! (1,009 reviews)
"Great location and clean."

Reviewed on Aug 11, 2025

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Americas Best Value Inn New Paltz
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! (1,007 reviews)
"Other than the arcade being a joke and taking our money while literally 2 games worked, we had a nice stay. Chose the hotel for pool and arcade, so slightly disappointed. Pool was nice, clean and warm. We had it to ourselves which was nice. Front desk staff was extremely friendly and helpful."

Reviewed on Aug 8, 2025

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Best Western Plus Kingston Hotel And Conference Center
Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

2.5 out of 5
4142 Albany Post Rd, Hyde Park, NY
Book a stay at this business-friendly hotel in Hyde Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,005 reviews)
"Kind staff, nice rooms (too small for our toddler to move around), nice breakfast: eggs, sausage, juices, waffle, etc. nice mix of hot and cold stuff. Will definitely come back!"

Reviewed on Aug 11, 2025

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Quality Inn Hyde Park Poughkeepsie North
See all 1,524 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.