Search Cheap Flights to
Poughkeepsie

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Poughkeepsie Flights as Low as $159

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

Breeze Airways
Thu, Jul 17 - Mon, Jul 21
MCO
Orlando Intl.
HPN
Westchester County
$159 Roundtrip, found 7 hours ago
$159
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Thu, Jul 17 from Orlando Intl. to Westchester County, returning Mon, Jul 21, priced at $159 found 7 hours ago
JetBlue Airways
Tue, Jul 22 - Sat, Jul 26
MCO
Orlando Intl.
HPN
Westchester County
$160 Roundtrip, found 5 hours ago
$160
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Tue, Jul 22 from Orlando Intl. to Westchester County, returning Sat, Jul 26, priced at $160 found 5 hours ago
Breeze Airways
Fri, Jul 18 - Fri, Jul 25
MCO
Orlando Intl.
HPN
Westchester County
$162 Roundtrip, found 1 day ago
$162
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jul 18 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $162 found 1 day ago
Breeze Airways
Fri, Jul 18 - Fri, Jul 25
MCO
Orlando Intl.
HPN
Westchester County
$162 Roundtrip, found 1 day ago
$162
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jul 18 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $162 found 1 day ago
Breeze Airways
Mon, Jul 21 - Fri, Jul 25
MCO
Orlando Intl.
HPN
Westchester County
$163 Roundtrip, found 7 hours ago
$163
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Mon, Jul 21 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $163 found 7 hours ago
Breeze Airways
Thu, Jul 24 - Tue, Jul 29
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 7 hours ago
$164
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Thu, Jul 24 from Orlando Intl. to Stewart Intl., returning Tue, Jul 29, priced at $164 found 7 hours ago
Breeze Airways
Fri, Jul 18 - Fri, Jul 25
MCO
Orlando Intl.
HPN
Westchester County
$167 Roundtrip, found 1 day ago
$167
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jul 18 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $167 found 1 day ago
Breeze Airways
Mon, Jul 21 - Fri, Jul 25
MCO
Orlando Intl.
HPN
Westchester County
$168 Roundtrip, found 7 hours ago
$168
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Mon, Jul 21 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $168 found 7 hours ago
Breeze Airways
Thu, Jul 24 - Tue, Jul 29
MCO
Orlando Intl.
SWF
Stewart Intl.
$170 Roundtrip, found 7 hours ago
$170
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Thu, Jul 24 from Orlando Intl. to Stewart Intl., returning Tue, Jul 29, priced at $170 found 7 hours ago
JetBlue Airways
Tue, Jul 22 - Sat, Jul 26
MCO
Orlando Intl.
HPN
Westchester County
$170 Roundtrip, found 5 hours ago
$170
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Tue, Jul 22 from Orlando Intl. to Westchester County, returning Sat, Jul 26, priced at $170 found 5 hours ago
American Airlines
Tue, Jul 22 - Sat, Jul 26
MCO
Orlando Intl.
HPN
Westchester County
$179 Roundtrip, found 5 hours ago
$179
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Tue, Jul 22 from Orlando Intl. to Westchester County, returning Sat, Jul 26, priced at $179 found 5 hours ago
Delta
Tue, Jul 22 - Sat, Jul 26
MCO
Orlando Intl.
HPN
Westchester County
$200 Roundtrip, found 5 hours ago
$200
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Jul 22 from Orlando Intl. to Westchester County, returning Sat, Jul 26, priced at $200 found 5 hours ago
Breeze Airways
Tue, Jul 15 - Sat, Jul 19
CHS
Charleston Intl.
HPN
Westchester County
$202 Roundtrip, found 1 day ago
$202
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Jul 15 from Charleston Intl. to Westchester County, returning Sat, Jul 19, priced at $202 found 1 day ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$206 Roundtrip, found 3 days ago
$206
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $206 found 3 days ago
Fly Play
Wed, Jul 9 - Wed, Aug 20
CDG
Roissy-Charles de Gaulle
SWF
Stewart Intl.
$759 Roundtrip, found 4 days ago
$759
Roundtrip
found 4 days ago
Select Fly Play flight, departing Wed, Jul 9 from Roissy-Charles de Gaulle to Stewart Intl., returning Wed, Aug 20, priced at $759 found 4 days ago
Fly Play
Sun, Jul 13 - Sat, Jul 19
PRG
Vaclav Havel
SWF
Stewart Intl.
$994 Roundtrip, found 22 hours ago
$994
Roundtrip
found 22 hours ago
Select Fly Play flight, departing Sun, Jul 13 from Vaclav Havel to Stewart Intl., returning Sat, Jul 19, priced at $994 found 22 hours ago

Cheap Flights to Poughkeepsie

Fall in love at first flight with your vacation to Poughkeepsie 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 Poughkeepsie on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Poughkeepsie, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Poughkeepsie

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Poughkeepsie 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 Poughkeepsie?

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 Poughkeepsie are in July, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Poughkeepsie?

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 Poughkeepsie.

What airport is best to fly into Poughkeepsie?

When you’re planning your trip to Poughkeepsie, convenience is the name of the game. Luckily, Poughkeepsie Stewart Intl. Airport is nearby so you can deplane and get going on checking off everything on your Poughkeepsie must-do list.

How much are flights to Poughkeepsie?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Poughkeepsie on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $159, 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 Poughkeepsie?

The trick to saving a stack of cash on your flight to Poughkeepsie? 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 $159 right now, why wait?

Poughkeepsie Flight Information
Destination airport
Westchester County
Destination airport IATA code
HPN
Roundtrip price
$199

Last Minute Hotel Deals in Poughkeepsie

Hampton Inn & Suites Poughkeepsie
Hampton Inn & Suites Poughkeepsie
2.5 out of 5
2361 South Rd, Poughkeepsie, NY
Book a stay at this golf hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
8.6/10 Excellent! (1,005 reviews)
"Nice room! Clean property!"

Reviewed on Jun 21, 2025

Get rates
Hampton Inn & Suites Poughkeepsie
DoubleTree by Hilton Poughkeepsie Convention Center
DoubleTree by Hilton Poughkeepsie Convention Center
4 out of 5
40 Civic Center Plz, Poughkeepsie, NY
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! (1,004 reviews)
"Friendly, clean, spacious, and perfectly located for our weekend plans. However, one of the two elevators was out of service the whole time we were there, and that made the wait around checkout time ridiculous. We were able to get parking in the garage every time we needed it, but we took the last ..."

Reviewed on Jun 8, 2025

Get rates
DoubleTree by Hilton Poughkeepsie Convention Center
The Heartwood
The Heartwood
2.5 out of 5
165 College Avenue, Poughkeepsie, NY
Stay at this hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Frances Lehman Loeb Art Center and Vassar Golf Course ...
9.8/10 Exceptional! (159 reviews)
"Nice location, near Vassar College. Modern and well designed and furnished rooms. Tasty restaurant."

Reviewed on Jun 23, 2025

Get rates
The Heartwood
Hyatt Place Poughkeepsie / Hudson Valley
Hyatt Place Poughkeepsie / Hudson Valley
3 out of 5
2165 South Road, Poughkeepsie, NY
Stay at this 3-star business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
8.6/10 Excellent! (1,002 reviews)
"Great stay"

Reviewed on Jun 20, 2025

Get rates
Hyatt Place Poughkeepsie / Hudson Valley
Courtyard by Marriott Poughkeepsie
Courtyard by Marriott Poughkeepsie
3 out of 5
2641 South Road/Route 9, Poughkeepsie, NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,001 reviews)
"It was just one night and it was great!"

Reviewed on Jun 21, 2025

Get rates
Courtyard by Marriott Poughkeepsie
Holiday Inn Poughkeepsie by IHG
Holiday Inn Poughkeepsie by IHG
3 out of 5
2170 South Rd, Poughkeepsie, NY
Stay at this 3-star business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (743 reviews)
"From checking In to checking out, I had an amazing experience."

Reviewed on Jun 22, 2025

Get rates
Holiday Inn Poughkeepsie by IHG
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)
"The hot breakfast has such a wide selection, the beds are super comfortable, the linens and towels are crisp and clean, room is in great condition. Sorry to see the pool is not and will not be in service. Gym was decent. Not a lot of people attending so there was no wait to use machines. I love the ..."

Reviewed on Jun 20, 2025

Get rates
Holiday Inn Express Poughkeepsie by IHG
Home2 Suites By Hilton Poughkeepsie
Home2 Suites By Hilton Poughkeepsie
3 out of 5
2619 South Road, Poughkeepsie, NY
Stay at this 3-star business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Locust Grove and McCann Golf ...
9.2/10 Wonderful! (268 reviews)
"A wonderful stay was had! The facility is central to food and shopping! The facility is very clean, the staff ver hospitable. We thoroughly enjoyed our stay!"

Reviewed on Jun 22, 2025

Get rates
Home2 Suites By Hilton Poughkeepsie
See all 2,484 properties in Poughkeepsie
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.