Flights To Dutchess County - Cheap Flights Starting at CA $65

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Poughkeepsie

Flights
Poughkeepsie

How Much Does it Cost To Fly To Dutchess County?

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

Thu, Jan 7 - Wed, Jan 13
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $112 Roundtrip, found 15 hours ago
CA $112
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Thu, Jan 7 from Raleigh - Durham Intl. to Westchester County, returning Wed, Jan 13, priced at CA $112 found 15 hours ago
Sat, Sep 12 - Tue, Sep 22
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $129 Roundtrip, found 6 days ago
CA $129
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Sep 12 from Raleigh - Durham Intl. to Westchester County, returning Tue, Sep 22, priced at CA $129 found 6 days ago
Fri, Oct 30 - Sun, Nov 1
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $148 Roundtrip, found 6 days ago
CA $148
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Oct 30 from Raleigh - Durham Intl. to Westchester County, returning Sun, Nov 1, priced at CA $148 found 6 days ago
Mon, Sep 14 - Thu, Sep 17
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $150 Roundtrip, found 5 days ago
CA $150
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Mon, Sep 14 from Raleigh - Durham Intl. to Westchester County, returning Thu, Sep 17, priced at CA $150 found 5 days ago
Wed, Oct 14 - Mon, Oct 19
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $194 Roundtrip, found 5 days ago
CA $194
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Oct 14 from Raleigh - Durham Intl. to Westchester County, returning Mon, Oct 19, priced at CA $194 found 5 days ago
Sat, Oct 3 - Sat, Oct 10
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
CA $199 Roundtrip, found 3 days ago
CA $199
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Oct 3 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Oct 10, priced at CA $199 found 3 days ago
Thu, Sep 10 - Wed, Sep 23
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $209 Roundtrip, found 3 days ago
CA $209
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Stewart Intl., returning Wed, Sep 23, priced at CA $209 found 3 days ago
Mon, Sep 14 - Wed, Sep 23
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $210 Roundtrip, found 3 days ago
CA $210
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Mon, Sep 14 from Orlando Intl. to Stewart Intl., returning Wed, Sep 23, priced at CA $210 found 3 days ago
Sat, Sep 12 - Tue, Sep 22
YYZ
Pearson Intl.
HPN
Westchester County
CA $517 Roundtrip, found 1 day ago
CA $517
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 12 from Pearson Intl. to Westchester County, returning Tue, Sep 22, priced at CA $517 found 1 day ago
Sat, Sep 12 - Tue, Sep 22
YYZ
Pearson Intl.
HPN
Westchester County
CA $517 Roundtrip, found 1 day ago
CA $517
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Sep 12 from Pearson Intl. to Westchester County, returning Tue, Sep 22, priced at CA $517 found 1 day ago
Thu, Sep 10 - Sat, Sep 19
YYZ
Pearson Intl.
HPN
Westchester County
CA $594 Roundtrip, found 1 day ago
CA $594
Roundtrip
found 1 day ago
Select WestJet flight, departing Thu, Sep 10 from Pearson Intl. to Westchester County, returning Sat, Sep 19, priced at CA $594 found 1 day ago
OriginDestinationTravel datesFlights from*
MCONewburghSeptember 10 to September 23CA $209
TPANewburghSeptember 9 to September 12CA $217
FLLWest HarrisonOctober 2 to October 4CA $311
MCOWest HarrisonSeptember 25 to September 27CA $338
TPAWest HarrisonSeptember 12 to September 15CA $338
DJTWest HarrisonSeptember 23 to October 3CA $344
RSWWest HarrisonSeptember 12 to September 19CA $412
ATLWest HarrisonOctober 24 to November 14CA $428
JAXWest HarrisonNovember 5 to November 8CA $641
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
MCONewburghAugust 28 to August 30CA $579
FLLWest HarrisonAugust 28 to September 6CA $597
RSWWest HarrisonAugust 28 to September 1CA $699
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square
4.0-star property

Hotel Riu Plaza Manhattan Times Square

Oct 2 - Oct 5

3 night stay

Buffalo (BUF) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Price was CA $2,161, price is now CA $1,300 per person
CA $1,300
per person
found 1 day ago
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

Oct 2 - Oct 5

3 night stay

Buffalo (BUF) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Price was CA $3,566, price is now CA $1,780 per person
CA $1,780
per person
found 1 day ago
The Towers at Lotte New York Palace
5.0-star property

The Towers at Lotte New York Palace

Oct 19 - Oct 23

4 night stay

Toronto (YTO) to New York (JFK)

Porter Airlines • Roundtrip • Coach
Price was CA $5,322, price is now CA $3,264 per person
CA $3,264
per person
found 1 day ago
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Travelers ❤️ These Dutchess County 🏨

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions SplashDown Beach and Bananas Comedy Club are located nearby.
Opens in a new windowHyatt Place Poughkeepsie / Hudson Valley
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
Book a stay at this business-friendly inn in Rhinebeck. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Starr Library and Dutchess County Fairgrounds are located nearby.
Opens in a new windowBeekman Arms and Delamater Inn
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. Popular attractions Locust Grove and McCann Golf Course are located nearby.
8.8/10 Excellent! (1,014 reviews)
"No comments"

Reviewed on Aug 21, 2026

Opens in a new windowHoliday Inn Express Poughkeepsie by IHG
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DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz Poughkeepsie NY
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions McCann Ice Arena and Cunneen-Hackett Cultural Center are located nearby.
Opens in a new windowDoubleTree by Hilton Poughkeepsie Convention Center
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.

Frequently asked questions

How much is the cheapest flight to Dutchess County?
The next trip you take doesn't have to make a huge dent in your budget. In the last seven days, the cheapest roundtrip flight to Dutchess County cost CA $112. Find your ideal fare and spend the dollars you save on awesome experiences. This price was available on Travelocity for flights to Dutchess County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Dutchess County?
You can pick from 20 airline companies when you want to lock in your flight to Dutchess County. Let Allegiant Air fly you there. This highly rated carrier has 26 services a month to Poughkeepsie, Dutchess County's gateway city.
What is the cheapest month to fly to Dutchess County?
If you're planning a getaway in Dutchess County, January is the cheapest month to travel there. This is according to Travelocity's direct return flight demand from January to December last year. Select your ideal travel dates and reserve your seat today.
How can I check my flight status to Dutchess County?
"Trips" is your one-stop shop when it comes to the ins and outs of your flight to Dutchess County. This handy customer portal lets you organize everything in the one place, from checking your flight status to updating or canceling your booking. Click on Trips at the top of the Travelocity homepage and then create an account or sign in. Alternatively, download the Travelocity app and access your info on the go. Whether you have the family flying with you or you're a solo wanderer, all your bookings are right there in your grasp.
How do I find the best deals on flights to Dutchess County?
It's wise to book well in advance, and if you can, avoid flying during the busy tourist season. Another smart way to save is by clicking the "Flexible dates" box at the top of the page after searching for your flights. This lets you compare prices for nearby days. In the last seven days, the lowest price for a return flight to Dutchess County was CA $112. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Dutchess County with Travelocity?
A memorable vacation is only a click of a button away when you arrange your trip with Travelocity. With great deals on cheap family flights, places to stay and more, we make it easy to locate the best prices to suit your needs. You can also enjoy our 24/7 customer assistance and free cancellations on most hotels throughout every step of the process. Wander wisely with us and snag your cheap flights to Dutchess County today.
What are the most popular flight routes to Dutchess County?
To help you choose your flights to Dutchess County, here's our list of some of the major routes:

  • Myrtle Beach, SC (MYR-Myrtle Beach Intl.) to Stewart Intl. Airport (SWF) - 17 flights a month.
  • St. Petersburg, FL (PIE-St. Petersburg-Clearwater Intl.) to Stewart Intl. Airport (SWF) - 8 flights a month.
  • Savannah, GA (SAV-Savannah - Hilton Head Intl.) to Stewart Intl. Airport (SWF) - 8 flights a month.

How much is a flight to Dutchess County on average?
Get your next break off to a great start by picking up an incredible deal with Travelocity. In the last seven days, roundtrip flights to Dutchess County cost between CA $112 and CA $699. Browse our site and secure an airfare that matches your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.