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

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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.

OriginDestinationTravel DatesFlights From*
FLLNewburghDecember 3 to December 6$86
PIENewburghNovember 1 to November 15$132
MCONewburghOctober 3 to October 3$147
MCOWest HarrisonOctober 28 to November 17$168
RSWNewburghOctober 3 to October 7$206
FLLWest HarrisonDecember 7 to December 10$224
JAXWest HarrisonOctober 20 to October 27$242
DJTWest HarrisonOctober 27 to November 3$251
TPAWest HarrisonOctober 30 to November 2$251
RSWWest HarrisonNovember 2 to November 5$314
ATLWest HarrisonOctober 28 to October 31$338
ORDWest HarrisonNovember 11 to November 16$417
CLTWest HarrisonOctober 7 to October 10$455
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCONewburghSeptember 19 to September 30$186
TPANewburghSeptember 19 to September 26$237
RSWNewburghSeptember 19 to September 23$240
TPAWest HarrisonSeptember 19 to September 29$391
MCOWest HarrisonSeptember 19 to September 24$445
DJTWest HarrisonSeptember 20 to October 29$478
RSWWest HarrisonSeptember 19 to September 22$527
CLTWest HarrisonSeptember 18 to September 21$590
FLLWest HarrisonSeptember 20 to September 21$625
ATLWest HarrisonSeptember 18 to September 21$706
JAXWest HarrisonSeptember 19 to September 26$1,060
ORDWest HarrisonSeptember 18 to September 21$1,284
*Prices include taxes and fees

Best Dutchess County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Lotte New York Palace
Beechmont - Perfect for Family Retreat!
The William Hotel Midtown, New York
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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! (1,015 reviews)
"The Beekman Arms is conveniently located in the heart of downtown Rhinebeck, walking distance to great restaurants and shops. The rooms are dated, but clean, comfortable, and quite spacious. The staff is amazing."

Reviewed on Sep 14, 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.
9/10 Wonderful! (1,070 reviews)
"Fantastic staff, very clean room and a great breakfast. Highly recommend this hotel"

Reviewed on Sep 14, 2026

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.
8.8/10 Excellent! (1,004 reviews)
"The room was clean and quiet. The mattress was on the soft side. The toilet made a screeching sound for a few minutes after use that thankfully stopped. The bathroom was quite dated. There is a complimentary breakfast with pre-made omlettes, toast, cereal etc with paper plates and plastic cutlery. ..."

Reviewed on Sep 13, 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 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, 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 $1,284. 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.