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 9 hours ago
CA $112
Roundtrip
found 9 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 9 hours ago
Mon, Sep 14 - Thu, Sep 17
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $150 Roundtrip, found 6 days ago
CA $150
Roundtrip
found 6 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 6 days ago
Wed, Oct 14 - Mon, Oct 19
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $194 Roundtrip, found 6 days ago
CA $194
Roundtrip
found 6 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 6 days ago
Sat, Oct 3 - Sat, Oct 10
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
CA $199 Roundtrip, found 4 days ago
CA $199
Roundtrip
found 4 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 4 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
Wed, Sep 30 - Sun, Oct 4
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $234 Roundtrip, found 3 days ago
CA $234
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Sep 30 from Orlando Intl. to Stewart Intl., returning Sun, Oct 4, priced at CA $234 found 3 days ago
Wed, Sep 30 - Mon, Oct 5
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $236 Roundtrip, found 3 days ago
CA $236
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Sep 30 from Orlando Intl. to Stewart Intl., returning Mon, Oct 5, priced at CA $236 found 3 days ago
Sat, Sep 12 - Tue, Sep 22
YYZ
Pearson Intl.
HPN
Westchester County
CA $517 Roundtrip, found 8 hours ago
CA $517
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, Sep 12 from Pearson Intl. to Westchester County, returning Tue, Sep 22, priced at CA $517 found 8 hours ago
Sat, Sep 12 - Tue, Sep 22
YYZ
Pearson Intl.
HPN
Westchester County
CA $517 Roundtrip, found 8 hours ago
CA $517
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Sat, Sep 12 from Pearson Intl. to Westchester County, returning Tue, Sep 22, priced at CA $517 found 8 hours ago
Sat, Sep 12 - Tue, Sep 22
YYZ
Pearson Intl.
HPN
Westchester County
CA $560 Roundtrip, found 8 hours ago
CA $560
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Sat, Sep 12 from Pearson Intl. to Westchester County, returning Tue, Sep 22, priced at CA $560 found 8 hours 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 $332
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 HarrisonOctober 23 to October 26CA $433
*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.
Seven Beach Lane
2.0-star property

Seven Beach Lane

Oct 4 - Oct 10

6 night stay

Toronto (YYZ) to New York (JFK)

Delta • Coach

New York (JFK) to Toronto (YYZ)

American Airlines • Coach
Price was CA $2,623, price is now CA $1,683 per person
CA $1,683
per person
found 1 day ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Aug 29 - Sep 5

7 night stay

Toronto (YTO) to New Haven (HVN)

Air Canada • Roundtrip • Coach
Price was CA $7,124, price is now CA $3,472 per person
CA $3,472
per person
found 1 day ago
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

Oct 7 - Oct 11

4 night stay

Toronto (YTO) to New York (JFK)

Delta • Coach

New York (JFK) to Toronto (YTO)

American Airlines • Coach
Price was CA $4,895, price is now CA $2,672 per person
CA $2,672
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.
9/10 Wonderful! (1,050 reviews)
"Déjeuner vraiment bon et complet. Tout était bien les matelas de notre chambre était soso mais sinon tout était très bien"

Reviewed on Aug 22, 2026

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.
8.2/10 Very good! (984 reviews)
"Very nice walk through history in this gorgeous Inn. Centrally located and walkable to all the town has to offer. I loved the room - so nicely appointed - even included sherry! The towels even had a lavender smell to them which was a nice touch."

Reviewed on Aug 21, 2026

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.