Flights To Dutchess County - Cheap Flights Starting at CA $98

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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, Sep 10 - Mon, Sep 14
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $220 Roundtrip, found 3 days ago
CA $220
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Stewart Intl., returning Mon, Sep 14, priced at CA $220 found 3 days ago
Thu, Aug 27 - Sun, Aug 30
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $243 Roundtrip, found 4 days ago
CA $243
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Aug 27 from Orlando Intl. to Stewart Intl., returning Sun, Aug 30, priced at CA $243 found 4 days ago
Thu, Jul 23 - Sat, Jul 25
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $254 Roundtrip, found 6 hours ago
CA $254
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Thu, Jul 23 from Orlando Intl. to Stewart Intl., returning Sat, Jul 25, priced at CA $254 found 6 hours ago
Tue, Sep 1 - Sun, Sep 6
MCO
Orlando Intl.
HPN
Westchester County
CA $257 Roundtrip, found 12 hours ago
CA $257
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando Intl. to Westchester County, returning Sun, Sep 6, priced at CA $257 found 12 hours ago
Thu, Oct 22 - Sun, Oct 25
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $259 Roundtrip, found 3 days ago
CA $259
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Oct 22 from Orlando Intl. to Stewart Intl., returning Sun, Oct 25, priced at CA $259 found 3 days ago
Thu, Sep 24 - Sat, Oct 3
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $265 Roundtrip, found 4 days ago
CA $265
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Sep 24 from Orlando Intl. to Stewart Intl., returning Sat, Oct 3, priced at CA $265 found 4 days ago
Wed, Sep 30 - Fri, Oct 2
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $270 Roundtrip, found 1 day ago
CA $270
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 30 from Orlando Intl. to Stewart Intl., returning Fri, Oct 2, priced at CA $270 found 1 day ago
Tue, Jul 21 - Sat, Jul 25
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $274 Roundtrip, found 2 days ago
CA $274
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Tue, Jul 21 from Orlando Intl. to Stewart Intl., returning Sat, Jul 25, priced at CA $274 found 2 days ago
Tue, Sep 1 - Wed, Sep 9
YYC
Calgary Intl.
HPN
Westchester County
CA $531 Roundtrip, found 9 hours ago
CA $531
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Sep 1 from Calgary Intl. to Westchester County, returning Wed, Sep 9, priced at CA $531 found 9 hours ago
Sat, Sep 12 - Sat, Sep 19
YYZ
Pearson Intl.
HPN
Westchester County
CA $534 Roundtrip, found 3 days ago
CA $534
Roundtrip
found 3 days ago
Select WestJet flight, departing Sat, Sep 12 from Pearson Intl. to Westchester County, returning Sat, Sep 19, priced at CA $534 found 3 days ago
Tue, Sep 1 - Wed, Sep 9
YYC
Calgary Intl.
HPN
Westchester County
CA $661 Roundtrip, found 9 hours ago
CA $661
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Sep 1 from Calgary Intl. to Westchester County, returning Wed, Sep 9, priced at CA $661 found 9 hours ago
OriginDestinationTravel datesFlights from*
MCONewburghSeptember 10 to September 14CA $220
MCOWest HarrisonSeptember 1 to September 6CA $257
TPAWest HarrisonSeptember 16 to September 22CA $337
PBIWest HarrisonJuly 28 to August 1CA $344
FLLWest HarrisonJuly 25 to August 1CA $359
JAXWest HarrisonAugust 22 to August 26CA $410
ORDWest HarrisonJuly 23 to July 26CA $577
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
MCONewburghJuly 11 to July 25CA $299
MCOWest HarrisonJuly 10 to July 12CA $545
TPAWest HarrisonJuly 12 to July 15CA $676
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Echo Valley Cottages
3.0-star property

Echo Valley Cottages

Aug 10 - Aug 17

7 night stay

Toronto (YYZ) to New York (JFK)

American Airlines • Non-stop roundtrip • Coach
Price was CA $1,980, price is now CA $1,332 per person
CA $1,332
per person
found 1 day ago
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

Aug 6 - Aug 9

3 night stay

Montreal (YUL) to New York (JFK)

Air Canada • Roundtrip • Coach
Price was CA $3,514, price is now CA $2,204 per person
CA $2,204
per person
found 1 day ago
Hotel Riu Plaza Manhattan Times Square
4.0-star property

Hotel Riu Plaza Manhattan Times Square

Aug 9 - Aug 14

5 night stay

Halifax (YHZ) to Newark Liberty Intl. Airport (EWR)

Air Canada • Non-stop roundtrip • Coach
Price was CA $2,681, price is now CA $1,784 per person
CA $1,784
per person
found 1 day ago
Don't see what you're looking for?
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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 Casperkill Golf Club are located nearby.
9/10 Wonderful! (1,011 reviews)
"Almost new property! Good size rooms and an incredible breakfast!"

Reviewed on Jul 7, 2026

Opens in a new windowHyatt Place Poughkeepsie / Hudson Valley
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Book a stay at this golf hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Van Wyck Homestead Museum and Blodgett Memorial Library are located nearby.
8.4/10 Very good! (158 reviews)
"Room is clean, which is important to me. Staff is friendly, breakfast, ok."

Reviewed on Jul 6, 2026

Opens in a new windowSpark by Hilton Fishkill
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.
8.4/10 Very good! (1,010 reviews)
"Unfortunately the air conditioning was not working when we arrived. The staff told us before we checked in & we had the option to go elsewhere. We decided to stay because tge location was perfect for us. The parking garage was very clean & felt safe being there. The staff was outstanding, always ..."

Reviewed on Jul 7, 2026

Opens in a new windowDoubleTree by Hilton Poughkeepsie Convention Center
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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! (922 reviews)
"Overall, we enjoyed our stay, but it came close to being a disaster for us. Before we stayed our first night we came close to asking to cancel our reservation. This issue is that the Beekman Arms has multiple properties so one needs to be careful when booking a room. The photos do not indicate whether ..."

Reviewed on Jul 7, 2026

Opens in a new windowBeekman Arms and Delamater Inn
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 $220. 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, September 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 $220. 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 $220 and CA $676. 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.