Cheap Flights to Dutchess County from $43 (2026/2027)

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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, Dec 3 - Sun, Dec 6
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$86 Roundtrip, found 2 hours ago
$86
Roundtrip
found 2 hours ago
Select Allegiant Air flight, departing Thu, Dec 3 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Dec 6, priced at $86 found 2 hours ago
Thu, Dec 3 - Thu, Dec 10
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$90 Roundtrip, found 1 day ago
$90
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Thu, Dec 3 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Thu, Dec 10, priced at $90 found 1 day ago
Fri, Nov 13 - Mon, Nov 16
SFB
Orlando Sanford Intl.
SWF
Stewart Intl.
$94 Roundtrip, found 2 days ago
$94
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Fri, Nov 13 from Orlando Sanford Intl. to Stewart Intl., returning Mon, Nov 16, priced at $94 found 2 days ago
Sun, Nov 1 - Sun, Nov 15
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$99 Roundtrip, found 3 hours ago
$99
Roundtrip
found 3 hours ago
Select Allegiant Air flight, departing Sun, Nov 1 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Nov 15, priced at $99 found 3 hours ago
Fri, Nov 13 - Mon, Nov 16
SFB
Orlando Sanford Intl.
SWF
Stewart Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Fri, Nov 13 from Orlando Sanford Intl. to Stewart Intl., returning Mon, Nov 16, priced at $100 found 1 day ago
Thu, Nov 5 - Sun, Nov 15
PIE
St. Petersburg-Clearwater Intl.
SWF
Stewart Intl.
$140 Roundtrip, found 1 day ago
$140
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Thu, Nov 5 from St. Petersburg-Clearwater Intl. to Stewart Intl., returning Sun, Nov 15, priced at $140 found 1 day ago
Thu, Jan 21 - Sat, Jan 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$146 Roundtrip, found 6 days ago
$146
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Jan 21 from Orlando Intl. to Stewart Intl., returning Sat, Jan 23, priced at $146 found 6 days ago
Tue, Oct 27 - Tue, Nov 17
MCO
Orlando Intl.
HPN
Westchester County
$152 Roundtrip, found 3 days ago
$152
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Oct 27 from Orlando Intl. to Westchester County, returning Tue, Nov 17, priced at $152 found 3 days ago
OriginDestinationTravel DatesFlights From*
FLLNewburghDecember 3 to December 6$86
PIENewburghNovember 1 to November 15$140
MCONewburghOctober 14 to October 17$150
MCOWest HarrisonNovember 3 to November 10$151
RSWNewburghOctober 3 to October 28$205
FLLWest HarrisonOctober 30 to November 1$227
TPAWest HarrisonOctober 30 to November 2$245
DJTWest HarrisonNovember 10 to November 18$251
RSWWest HarrisonDecember 14 to December 16$332
JAXWest HarrisonNovember 25 to November 26$358
ATLWest HarrisonOctober 21 to October 28$372
ORDWest HarrisonNovember 20 to November 21$437
CLTWest HarrisonOctober 14 to October 18$462
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCONewburghSeptember 26 to October 3$198
RSWNewburghSeptember 26 to October 3$232
PIENewburghSeptember 27 to October 4$241
RSWWest HarrisonSeptember 27 to October 2$433
MCOWest HarrisonSeptember 25 to September 28$474
FLLWest HarrisonSeptember 25 to September 27$487
TPAWest HarrisonSeptember 26 to September 28$498
ORDWest HarrisonSeptember 25 to September 28$523
CLTWest HarrisonSeptember 25 to September 26$548
DJTWest HarrisonSeptember 26 to October 1$549
ATLWest HarrisonSeptember 26 to October 5$568
*Prices include taxes and fees

Best Dutchess County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Nov 6 - Nov 8

2 night stay

Atlanta (ATL) to New Haven (HVN)

Xtra Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,574, price is now $886 per person
$886
per person
found 1 day ago
Lotte New York Palace
4.5-star property

Lotte New York Palace

Dec 7 - Dec 10

3 night stay

Atlanta (ATL) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Price was $2,618, price is now $1,282 per person
$1,282
per person
found 1 day ago
Ink 48 Hotel
4.5-star property

Ink 48 Hotel

Dec 10 - Dec 15

5 night stay

Atlanta (ATL) to New York (JFK)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,938, price is now $1,088 per person
$1,088
per person
found 1 day ago
Don't see what you're looking for?
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Travelers ❤️ These Dutchess County 🏨

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 rooms in our reviews. Popular attractions Frances Lehman Loeb Art Center and Vassar Golf Course are located nearby.
Opens in a new windowQuality Inn Poughkeepsie
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! (1,008 reviews)
"Very nice place. Old and cozy. Had a fireplace in our room which was rather large and even had a decanter of sherry which was a nice touch. Location was great and within walking distance to the fairgrounds which is why we were visiting for the Hudson Valley wine and food festival"

Reviewed on Sep 19, 2026

Opens in a new windowBeekman Arms and Delamater Inn
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 Bananas Comedy Club and Casperkill Golf Club are located nearby.
Opens in a new windowHyatt Place Poughkeepsie / Hudson Valley
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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.
8.6/10 Excellent! (1,004 reviews)
"The room was large and clean if not a bit outdated, especially the bathroom and the carpet in the room. A few times while walking the hall there was a slight odor of dampness."

Reviewed on Sep 18, 2026

Opens in a new windowHoliday Inn Express Poughkeepsie by IHG
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 $86. 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 15 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, December 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 $86. 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 $86 and $568. 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.
How long is the average flight to Dutchess County?
The length of your direct flight to Dutchess County depends on your departure point. So you know what to expect, here are the average flight times for some top routes to Dutchess County:

  • Myrtle Beach, SC (MYR-Myrtle Beach Intl.) to Stewart Intl. Airport (SWF) - 1 hour and 50 minutes
  • St. Petersburg, FL (PIE-St. Petersburg-Clearwater Intl.) to Stewart Intl. Airport (SWF) - 2 hours and 45 minutes
  • Savannah, GA (SAV-Savannah - Hilton Head Intl.) to Stewart Intl. Airport (SWF) - 1 hour and 57 minutes

What can I expect on a flight to Dutchess County?
If you're about to hop on a long-haul flight to Dutchess County, you can normally expect meals, drinks and entertainment on board. Airlines endeavor to make longer flights as comfortable as they can for passengers. Shorter trips — as well as flights offered by low-cost airlines — may not have such inclusions. If you're after cheap flights for family vacations with a low-priced carrier, it's likely you'll pay extra for things like snacks and drinks.