Search Cheap Flights toHighland
Photo by Karen Wirtz
Search 400 airlines and 321,000 hotels worldwide.
Stop Planning & Start Exploring
FREE 24 hour cancellation on most flights
Highland Flights as Low as $117
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, Feb 28 - Sun, Mar 2
MCO
Orlando Intl.
SWF
Stewart Intl.
$117 Roundtrip, found 4 hours ago
$117
Roundtrip
found 4 hours ago
Thu, May 1 - Sun, May 4
MCO
Orlando Intl.
SWF
Stewart Intl.
$122 Roundtrip, found 11 hours ago
$122
Roundtrip
found 11 hours ago
Tue, Mar 25 - Sun, Mar 30
MCO
Orlando Intl.
SWF
Stewart Intl.
$127 Roundtrip, found 3 hours ago
$127
Roundtrip
found 3 hours ago
Thu, Jan 30 - Sun, Feb 2
MCO
Orlando Intl.
SWF
Stewart Intl.
$155 Roundtrip, found 6 days ago
$155
Roundtrip
found 6 days ago
Fri, May 2 - Sun, May 4
MCO
Orlando Intl.
SWF
Stewart Intl.
$156 Roundtrip, found 3 days ago
$156
Roundtrip
found 3 days ago
Fri, Jan 24 - Mon, Jan 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Thu, Feb 20 - Sun, Feb 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$206 Roundtrip, found 3 days ago
$206
Roundtrip
found 3 days ago
Fri, Jan 24 - Sun, Jan 26
MCO
Orlando Intl.
SWF
Stewart Intl.
$213 Roundtrip, found 16 hours ago
$213
Roundtrip
found 16 hours ago
Fri, Apr 25 - Sun, Apr 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$243 Roundtrip, found 1 day ago
$243
Roundtrip
found 1 day ago
Fri, Feb 14 - Mon, Feb 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$321 Roundtrip, found 5 days ago
$321
Roundtrip
found 5 days ago
Sun, Jun 1 - Mon, Jun 16
DUB
Dublin
SWF
Stewart Intl.
$721 Roundtrip, found 12 hours ago
$721
Roundtrip
found 12 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 February, 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 11 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?
Destination airport | Stewart Intl. |
Destination airport IATA code | SWF |
Roundtrip price | $117 |
Last Minute Hotel Deals in Highland
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W, I-87 Exit 18 to I-9W, Highland, NY
The price is $120 per night from Jan 29 to Jan 30
$120
includes taxes & fees
Jan 29 - Jan 30
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! (800 reviews)
"Super cute and charming accommodations. Room was modern and very clean. Complimentary coffee and hot chocolate in lobby was a nice touch on a very cold winter day! Lobby also very clean and decorated nicely. There weren’t any smells as some hotels / motels may have. I was very pleased and felt the ..."
Reviewed on Jan 9, 2025
Rodeway Inn & Suites New Paltz - Hudson Valley
601 Main Street, Highland, NY
The price is $101 per night from Jan 26 to Jan 27
$101
includes taxes & fees
Jan 26 - Jan 27
Stay at this motel in Highland. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.2/10 Good! (670 reviews)
"We had a very good experience. The only thing that made things a little difficult for us is that the bed in the room was very high off the floor. For shorter people, like my wife, that made getting into and out of bed harder than it should."
Reviewed on Nov 30, 2024
HYATT house Fishkill/Poughkeepsie
100 Westage Business Center Dr., Fishkill, NY
The price is $111 per night from Jan 31 to Feb 1
$111
includes taxes & fees
Jan 31 - Feb 1
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! (1,001 reviews)
"Everyone has been very helpful and even letting us arrange our schedule to check in early due to a snow storm during our travels."
Reviewed on Jan 20, 2025
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road, Poughkeepsie, NY
The price is $113 per night from Jan 24 to Jan 25
$113
includes taxes & fees
Jan 24 - Jan 25
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! (1,012 reviews)
"Second stay when visiting family from Atlanta. Looking forward to our next stay."
Reviewed on Jan 20, 2025
Best Western Fishkill Inn & Suites
14 Schuyler Blvd, Fishkill, NY
The price is $104 per night from Jan 30 to Jan 31
$104
includes taxes & fees
Jan 30 - Jan 31
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! (750 reviews)
"Amazing"
Reviewed on Jan 19, 2025
Wildflower Farms, Auberge Resorts Collection
2702 Main St, Gardiner, NY
The price is $1,050 per night from Feb 3 to Feb 4
$1,050
includes taxes & fees
Feb 3 - Feb 4
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! (43 reviews)
"Amazing getaway from the city!"
Reviewed on Jan 17, 2025
DoubleTree by Hilton Poughkeepsie
40 Civic Center Plz, Poughkeepsie, NY
The price is $122 per night from Jan 27 to Jan 28
$122
includes taxes & fees
Jan 27 - Jan 28
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! (1,001 reviews)
Great stay for a good price.
"Great room. High quality linens and towels. Nice bathroom. Staff was responsive with a noise issue."
Reviewed on Jan 12, 2025
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
25 OLD VINEYARD PLACE, Hyde Park, NY
The price is $161 per night from Feb 17 to Feb 18
$161
includes taxes & fees
Feb 17 - Feb 18
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! (246 reviews)
"My daughter goes to school right across the street from this hotel. I was one of the first guests when they first opened and it’s just absolutely beautiful, the staff are very friendly, but as the months have gone by. It’s gotten very expensive. I would love it if the price went down a little so ..."
Reviewed on Jan 21, 2025
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.
Popular Flight Routes
- Atlanta to New York
- Detroit to Las Vegas
- Dallas to Atlanta
- Dallas to Yosemite National Park
- Toronto to Edmonton
- Chicago to Tulum
- Houston to Lake Tahoe
- Chicago to Las Vegas
- Dallas to Miami
- Dallas to Lake Tahoe
- New York to Miami
- New York to Las Vegas
- Miami to Atlanta
- Minneapolis St Paul to Fort Walton Beach Destin
- Dallas to Branson
- Cleveland to Vero Beach
- Managua to Miami
- Atlanta to Boston
- Austin to Tulum
- Calgary to Vancouver
Flights to Our Favorite Destinations
- Flights to Las Vegas
- Flights to New York
- Flights to Orlando
- Flights to Miami
- Flights to Gatlinburg
- Flights to Key West
- Flights to Chicago
- Flights to San Diego
- Flights to Los Angeles
- Flights to Fort Lauderdale
- Flights to Honolulu
- Flights to New Orleans
- Flights to Nashville
- Flights to Pigeon Forge
- Flights to Kissimmee
- Flights to Boston
Top Highland Hotels
- Rodeway Inn & Suites New Paltz - Hudson Valley
- HYATT house Fishkill/Poughkeepsie
- Hyatt Place Poughkeepsie / Hudson Valley
- Best Western Fishkill Inn & Suites
- Courtyard by Marriott Kingston
- Hampton Inn by Hilton New Paltz
- Best Western Plus Kingston Hotel And Conference Center
- Hampton Inn & Suites Newburgh Stewart Airport
- Hampton Inn Kingston
- Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
- Courtyard by Marriott Poughkeepsie
- Homewood Suites by Hilton Poughkeepsie