Cheap Flights to Dutchess County from $51 (2026/2027)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Dutchess County's top cities

A river with boats docked on the shore, surrounded by autumn-colored trees.

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.

Wed, Dec 9 - Sat, Dec 12
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$102 Roundtrip, found 4 hours ago
$102
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Dec 9 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Dec 12, priced at $102 found 4 hours ago
Wed, Dec 2 - Wed, Jan 6
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$102 Roundtrip, just found
$102
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Dec 2 from Raleigh - Durham Intl. to Westchester County, returning Wed, Jan 6, priced at $102 just found
Sat, Jan 30 - Tue, Feb 2
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Jan 30 from Raleigh - Durham Intl. to Westchester County, returning Tue, Feb 2, priced at $107 found 2 days ago
Fri, Dec 4 - Tue, Dec 15
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$112 Roundtrip, found 2 hours ago
$112
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Raleigh - Durham Intl. to Westchester County, returning Tue, Dec 15, priced at $112 found 2 hours ago
Wed, Nov 18 - Wed, Dec 2
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Nov 18 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Dec 2, priced at $117 found 1 day ago
Tue, Nov 3 - Wed, Nov 4
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$122 Roundtrip, found 1 hour ago
$122
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Tue, Nov 3 from Raleigh - Durham Intl. to Westchester County, returning Wed, Nov 4, priced at $122 found 1 hour ago
Sat, Nov 14 - Tue, Nov 17
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$123 Roundtrip, found 6 days ago
$123
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Nov 14 from Raleigh - Durham Intl. to Westchester County, returning Tue, Nov 17, priced at $123 found 6 days ago
Thu, Feb 11 - Sat, Feb 20
PIE
St. Petersburg-Clearwater Intl.
SWF
Stewart Intl.
$132 Roundtrip, found 3 hours ago
$132
Roundtrip
found 3 hours ago
Select Allegiant Air flight, departing Thu, Feb 11 from St. Petersburg-Clearwater Intl. to Stewart Intl., returning Sat, Feb 20, priced at $132 found 3 hours ago
OriginDestinationTravel DatesFlights From*
FLLNewburghNovember 1 to November 15$100
PIENewburghJanuary 7 to January 10$141
MCOWest HarrisonNovember 12 to November 17$144
MCONewburghDecember 3 to December 6$147
RSWNewburghJanuary 9 to January 13$190
TPAWest HarrisonDecember 5 to December 11$205
FLLWest HarrisonDecember 11 to January 12$231
DJTWest HarrisonNovember 3 to November 7$233
JAXWest HarrisonNovember 7 to November 11$263
RSWWest HarrisonDecember 8 to December 15$297
CLTWest HarrisonNovember 18 to November 22$345
ATLWest HarrisonNovember 6 to November 8$410
ORDWest HarrisonDecember 19 to January 10$437
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCONewburghOctober 17 to October 24$250
FLLNewburghOctober 18 to October 25$270
RSWNewburghOctober 17 to October 21$332
MCOWest HarrisonOctober 17 to October 20$350
TPANewburghOctober 17 to November 4$378
FLLWest HarrisonOctober 16 to October 22$464
DJTWest HarrisonOctober 17 to October 27$483
ORDWest HarrisonOctober 17 to October 30$499
RSWWest HarrisonOctober 16 to October 18$535
TPAWest HarrisonOctober 17 to October 20$563
ATLWest HarrisonOctober 16 to October 18$613
CLTWest HarrisonOctober 16 to November 3$853
JAXWest HarrisonOctober 16 to October 20$1,072
*Prices include taxes and fees

Best Dutchess County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Seven Beach Lane
2.0-star property

Seven Beach Lane

Oct 30 - Nov 2

3 night stay

Orlando (MCO) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $973, price is now $579 per person
$579
per person
found 18 hours ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Oct 12 - Oct 15

3 night stay

Atlanta (ATL) to New Haven (HVN)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $3,271, price is now $1,711 per person
$1,711
per person
found 2 hours ago
Hotel Riu Plaza Manhattan Times Square
4.0-star property

Hotel Riu Plaza Manhattan Times Square

Dec 23 - Dec 27

4 night stay

Atlanta (ATL) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $2,174, price is now $1,267 per person
$1,267
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Orlando to Dutchess County
View all trips

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 Bananas Comedy Club and Casperkill Golf Club are located nearby.
9/10 Wonderful! (1,112 reviews)
"Guest room was designed well. Very clean. Comfortable bed. Great shower, strong pressure, like a massage. Breakfast was excellent , fresh and hot. Will be back"

Reviewed on Oct 10, 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.
Opens in a new windowBeekman Arms and Delamater Inn
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

2.5 out of 5
835 Route 52 Fishkill NY
Book a stay at this business-friendly 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 Blodgett Memorial Library and Fishkill Ridge are located nearby.
Opens in a new windowComfort Suites Fishkill near Interstate 84
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Studio 6 Extended Stay Fishkill Westage Center NY

Studio 6 Extended Stay Fishkill Westage Center NY

2.5 out of 5
55 W Merritt Blvd Fishkill NY
Stay at this hotel in Fishkill. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Van Wyck Homestead Museum and Fishkill Golf Course are located nearby.
6/10 (1,004 reviews)
"I had a reservation and the hotel over booked, NO ROOM!"

Reviewed on Oct 10, 2026

Opens in a new windowStudio 6 Extended Stay Fishkill Westage Center NY
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 $100. 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 $100. 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 $100 and $1,072. 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.