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 $161

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

American Airlines
Thu, Jul 3 - Mon, Jul 7
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$161 Roundtrip, found 3 days ago
$161
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Jul 3 from Raleigh - Durham Intl. to Westchester County, returning Mon, Jul 7, priced at $161 found 3 days ago
Breeze Airways
Mon, Jul 21 - Fri, Jul 25
MCO
Orlando Intl.
HPN
Westchester County
$161 Roundtrip, found 1 day ago
$161
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Jul 21 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $161 found 1 day ago
Breeze Airways
Mon, Jul 21 - Fri, Jul 25
MCO
Orlando Intl.
HPN
Westchester County
$164 Roundtrip, found 1 day ago
$164
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Jul 21 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $164 found 1 day ago
Breeze Airways
Mon, Jul 21 - 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 Mon, Jul 21 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $167 found 1 day ago
JetBlue Airways
Sat, Jul 19 - Mon, Jul 21
MCO
Orlando Intl.
HPN
Westchester County
$170 Roundtrip, found 2 days ago
$170
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, Jul 19 from Orlando Intl. to Westchester County, returning Mon, Jul 21, priced at $170 found 2 days ago
Breeze Airways
Mon, Jul 21 - Fri, Jul 25
MCO
Orlando Intl.
HPN
Westchester County
$172 Roundtrip, found 1 day ago
$172
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Jul 21 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $172 found 1 day ago
Breeze Airways
Tue, Jul 15 - Mon, Jul 21
CHS
Charleston Intl.
HPN
Westchester County
$175 Roundtrip, found 1 day ago
$175
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Jul 15 from Charleston Intl. to Westchester County, returning Mon, Jul 21, priced at $175 found 1 day ago
Breeze Airways
Tue, Jul 15 - Mon, Jul 21
CHS
Charleston Intl.
HPN
Westchester County
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Jul 15 from Charleston Intl. to Westchester County, returning Mon, Jul 21, priced at $180 found 1 day ago
Delta
Fri, Jul 4 - Tue, Jul 8
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$184 Roundtrip, found 1 day ago
$184
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 4 from Raleigh - Durham Intl. to Westchester County, returning Tue, Jul 8, priced at $184 found 1 day ago
JetBlue Airways
Tue, Jul 22 - Tue, Jul 22
MCO
Orlando Intl.
HPN
Westchester County
$185 Roundtrip, found 13 hours ago
$185
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Tue, Jul 22 from Orlando Intl. to Westchester County, returning Tue, Jul 22, priced at $185 found 13 hours ago
JetBlue Airways
Mon, Jul 21 - Fri, Jul 25
MCO
Orlando Intl.
HPN
Westchester County
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Jul 21 from Orlando Intl. to Westchester County, returning Fri, Jul 25, priced at $189 found 1 day ago
JetBlue Airways
Tue, Jul 22 - Tue, Jul 22
MCO
Orlando Intl.
HPN
Westchester County
$191 Roundtrip, found 13 hours ago
$191
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Tue, Jul 22 from Orlando Intl. to Westchester County, returning Tue, Jul 22, priced at $191 found 13 hours ago
American Airlines
Tue, Jul 22 - Tue, Jul 22
MCO
Orlando Intl.
HPN
Westchester County
$195 Roundtrip, found 13 hours ago
$195
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Tue, Jul 22 from Orlando Intl. to Westchester County, returning Tue, Jul 22, priced at $195 found 13 hours ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$206 Roundtrip, found 4 days ago
$206
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $206 found 4 days ago
Breeze Airways
Thu, Jul 3 - Sun, Jul 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jul 3 from Orlando Intl. to Stewart Intl., returning Sun, Jul 6, priced at $224 found 1 day ago
Breeze Airways
Mon, Jul 21 - Thu, Jul 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$506 Roundtrip, found 5 days ago
$506
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Mon, Jul 21 from Raleigh - Durham Intl. to Stewart Intl., returning Thu, Jul 24, priced at $506 found 5 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 $161, 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 $161 right now, why wait?

Poughkeepsie Flight Information
Destination airport
Westchester County
Destination airport IATA code
HPN
Roundtrip price
$200

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! (1,002 reviews)
"Great customer service"

Reviewed on Jun 11, 2025

Get rates
Hampton Inn & Suites Poughkeepsie
DoubleTree by Hilton Poughkeepsie
DoubleTree by Hilton Poughkeepsie
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! (1,002 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
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! (1,000 reviews)
"Room was very clean, loved the white sheets and blankets and staff was perfessional"

Reviewed on Jun 8, 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! (1,000 reviews)
"Clean and updated, nice stay."

Reviewed on Jun 7, 2025

Get rates
Courtyard by Marriott 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! (1,001 reviews)
"Very nice. Recently renovated and nicely done! Room was very comfortable- nice amenities with a Keurig and nice size refrigerator/freezer! Comfy mattress and pillows. Bathroom large and nice amenities!"

Reviewed on Jun 9, 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! (261 reviews)
"Great place. Definitely worth the stay"

Reviewed on Jun 7, 2025

Get rates
Home2 Suites By Hilton Poughkeepsie
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! (151 reviews)
"Environmentally carbon neutral in a beautiful, sophisticated, customer-service focused property"

Reviewed on Jun 13, 2025

Get rates
The Heartwood
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! (738 reviews)
"Older property, well kept, friendly staff. The only thing I didn’t like was my room was in the basement floor and across from my door is housekeeping. In the morning I could here staff rolling carts down their hall and out of that area."

Reviewed on Jun 8, 2025

Get rates
Holiday Inn Poughkeepsie by IHG
See all 2,473 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.