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Poughkeepsie

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Poughkeepsie Flights as Low as $166

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

Breeze Airways
Thu, Jul 24 - Mon, Jul 28
MCO
Orlando Intl.
HPN
Westchester County
$166 Roundtrip, found 4 days ago
$166
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jul 24 from Orlando Intl. to Westchester County, returning Mon, Jul 28, priced at $166 found 4 days ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$180 Roundtrip, found 3 days ago
$180
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Aug 14 from Orlando Intl. to Stewart Intl., returning Sun, Aug 17, priced at $180 found 3 days ago
Breeze Airways
Mon, Jul 28 - Thu, Jul 31
MCO
Orlando Intl.
HPN
Westchester County
$181 Roundtrip, found 1 day ago
$181
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Jul 28 from Orlando Intl. to Westchester County, returning Thu, Jul 31, priced at $181 found 1 day ago
Breeze Airways
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$183 Roundtrip, found 3 days ago
$183
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Jul 25 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $183 found 3 days ago
JetBlue Airways
Sat, Jul 26 - Mon, Jul 28
MCO
Orlando Intl.
HPN
Westchester County
$185 Roundtrip, found 4 days ago
$185
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sat, Jul 26 from Orlando Intl. to Westchester County, returning Mon, Jul 28, priced at $185 found 4 days ago
JetBlue Airways
Mon, Jul 28 - Thu, Jul 31
MCO
Orlando Intl.
HPN
Westchester County
$185 Roundtrip, found 1 day ago
$185
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Jul 28 from Orlando Intl. to Westchester County, returning Thu, Jul 31, priced at $185 found 1 day ago
Breeze Airways
Mon, Jul 28 - Thu, Jul 31
MCO
Orlando Intl.
HPN
Westchester County
$186 Roundtrip, found 1 day ago
$186
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Jul 28 from Orlando Intl. to Westchester County, returning Thu, Jul 31, priced at $186 found 1 day ago
Breeze Airways
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$188 Roundtrip, found 3 days ago
$188
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Jul 25 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $188 found 3 days ago
Breeze Airways
Thu, Jul 31 - Sun, Aug 3
MCO
Orlando Intl.
SWF
Stewart Intl.
$190 Roundtrip, found 4 hours ago
$190
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Thu, Jul 31 from Orlando Intl. to Stewart Intl., returning Sun, Aug 3, priced at $190 found 4 hours ago
Breeze Airways
Thu, Jul 24 - Tue, Jul 29
MCO
Orlando Intl.
SWF
Stewart Intl.
$190 Roundtrip, found 6 days ago
$190
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Jul 24 from Orlando Intl. to Stewart Intl., returning Tue, Jul 29, priced at $190 found 6 days ago
Breeze Airways
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$192 Roundtrip, found 2 days ago
$192
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jul 25 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $192 found 2 days ago
Breeze Airways
Fri, Jul 18 - Fri, Jul 25
MCO
Orlando Intl.
HPN
Westchester County
$192 Roundtrip, found 4 days ago
$192
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jul 18 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $192 found 4 days ago
Breeze Airways
Fri, Aug 1 - Sun, Aug 3
MCO
Orlando Intl.
SWF
Stewart Intl.
$193 Roundtrip, found 4 days ago
$193
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Stewart Intl., returning Sun, Aug 3, priced at $193 found 4 days ago
American Airlines
Mon, Jul 28 - Thu, Jul 31
MCO
Orlando Intl.
HPN
Westchester County
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Jul 28 from Orlando Intl. to Westchester County, returning Thu, Jul 31, priced at $200 found 1 day ago
Delta
Mon, Jul 28 - Thu, Jul 31
MCO
Orlando Intl.
HPN
Westchester County
$312 Roundtrip, found 1 day ago
$312
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Jul 28 from Orlando Intl. to Westchester County, returning Thu, Jul 31, priced at $312 found 1 day ago
Fly Play
Sat, Jul 19 - Sat, Jul 26
CDG
Roissy-Charles de Gaulle
SWF
Stewart Intl.
$755 Roundtrip, found 3 days ago
$755
Roundtrip
found 3 days ago
Select Fly Play flight, departing Sat, Jul 19 from Roissy-Charles de Gaulle to Stewart Intl., returning Sat, Jul 26, priced at $755 found 3 days 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 $166, 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 $166 right now, why wait?

Poughkeepsie Flight Information
Destination airport
Westchester County
Destination airport IATA code
HPN
Roundtrip price
$169

Last Minute Hotel Deals in Poughkeepsie

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 ...
7.8/10 Good! (368 reviews)
"Hotel was nicely situated to the walk way over the Hudson fireworks. Staff was very friendly. Suggestions-heat the pool. Also Room we were in was situated next to the stairwell. It was a little hard to sleep due to stairwell door slamming and people walking in stairwell throughout the evening. Would ..."

Reviewed on Jul 11, 2025

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Quality Inn 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! (1,004 reviews)
"We found this wonderful location to be just perfect!! Our check-in was a breeze, and the clerk was extremely accommodating. After a quiet night's rest we had the hotel's great hot breakfast. Plenty of free parking, right off a very convenient commercial corridor; I highly recommend this Holiday Inn, ..."

Reviewed on Jul 13, 2025

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Holiday Inn Express Poughkeepsie by IHG
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! (1,006 reviews)
"The staff was friendly and well trained. We added several rooms as my Kin showed up unexpectedly for this informal family reunion. The pool was great as well as the breakfast. I would have like to see housekeeping on the second day but on demand they provided fresh towels and trash removal. The EVS ..."

Reviewed on Jul 13, 2025

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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! (1,001 reviews)
Great visit!
"From the time I arrived the stay was perfect. The staff at the desk, the informative way I was checked in…. The cookies ❤️❤️❤️❤️. The room was perfect, loved the shower. Loved the size of the room and the TV. I ate breakfast on the second day. Trinity was fantastic as was the young bus boy, very ..."

Reviewed on Jul 10, 2025

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DoubleTree by Hilton Poughkeepsie Convention Center
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! (752 reviews)
"Very quiet"

Reviewed on Jul 8, 2025

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Holiday Inn Poughkeepsie by IHG
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! (168 reviews)
"The hotel is modern but so warm and inviting. The beds are extremely comfortable. The complimentary breakfast was tasty and I truly appreciated being able to order a cappuccino as well. Perfect stop on our road trip through Vassar!"

Reviewed on Jul 8, 2025

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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! (1,003 reviews)
"I like everything."

Reviewed on Jul 1, 2025

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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 ...
8.8/10 Excellent! (1,008 reviews)
"Staff was amazing"

Reviewed on Jul 13, 2025

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Courtyard by Marriott Poughkeepsie
See all 2,487 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.