Cheap Flights to Dutchess County from $41 (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.

Fri, Sep 11 - Mon, Sep 14
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$82 Roundtrip, found 1 day ago
$82
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Sep 11 from Raleigh - Durham Intl. to Westchester County, returning Mon, Sep 14, priced at $82 found 1 day ago
Wed, Sep 9 - Sat, Sep 12
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$87 Roundtrip, just found
$87
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Sep 9 from Raleigh - Durham Intl. to Westchester County, returning Sat, Sep 12, priced at $87 just found
Wed, Aug 26 - Mon, Aug 31
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$92 Roundtrip, found 1 hour ago
$92
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Wed, Aug 26 from Raleigh - Durham Intl. to Westchester County, returning Mon, Aug 31, priced at $92 found 1 hour ago
Thu, Sep 17 - Mon, Sep 21
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$97 Roundtrip, found 14 hours ago
$97
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Thu, Sep 17 from Raleigh - Durham Intl. to Westchester County, returning Mon, Sep 21, priced at $97 found 14 hours ago
Sat, Sep 26 - Wed, Sep 30
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Sep 26 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Sep 30, priced at $102 found 1 day ago
Wed, Sep 16 - Wed, Sep 23
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$102 Roundtrip, found 15 hours ago
$102
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Wed, Sep 16 from Raleigh - Durham Intl. to Westchester County, returning Wed, Sep 23, priced at $102 found 15 hours ago
Fri, Oct 2 - Sat, Oct 10
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Oct 2 from Raleigh - Durham Intl. to Westchester County, returning Sat, Oct 10, priced at $107 found 1 day ago
Thu, Sep 3 - Sun, Sep 6
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$109 Roundtrip, found 1 day ago
$109
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 3 from Raleigh - Durham Intl. to Westchester County, returning Sun, Sep 6, priced at $109 found 1 day ago
Tue, Aug 25 - Fri, Aug 28
MCO
Orlando Intl.
HPN
Westchester County
$116 Roundtrip, found 4 days ago
$116
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Tue, Aug 25 from Orlando Intl. to Westchester County, returning Fri, Aug 28, priced at $116 found 4 days ago
OriginDestinationTravel DatesFlights From*
TPANewburghSeptember 12 to September 16$130
MCONewburghSeptember 10 to September 16$142
MCOWest HarrisonAugust 25 to August 26$147
TPAWest HarrisonAugust 26 to September 1$185
RSWNewburghSeptember 12 to September 16$194
PBIWest HarrisonSeptember 23 to September 27$209
RSWWest HarrisonAugust 10 to August 14$210
FLLWest HarrisonSeptember 29 to October 1$214
JAXWest HarrisonJuly 30 to August 4$259
ATLWest HarrisonJuly 22 to July 29$284
ORDWest HarrisonOctober 17 to October 24$395
CLTWest HarrisonSeptember 5 to September 6$396
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCONewburghJuly 11 to July 18$240
TPAWest HarrisonJuly 11 to July 18$295
RSWNewburghJuly 11 to July 25$308
MCOWest HarrisonJuly 12 to July 13$346
RSWWest HarrisonJuly 12 to July 18$403
PBIWest HarrisonJuly 11 to July 13$420
FLLWest HarrisonJuly 11 to August 2$431
CLTWest HarrisonJuly 11 to July 18$460
JAXWest HarrisonJuly 12 to July 19$464
TPANewburghJuly 11 to July 18$466
ORDWest HarrisonJuly 10 to July 11$499
ATLWest HarrisonJuly 10 to July 13$655
*Prices include taxes and fees

Best Dutchess County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel St. James
3.0-star property

Hotel St. James

Aug 19 - Aug 23

4 night stay

Atlanta (ATL) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Price was $878, price is now $446 per person
$446
per person
found 1 day ago
2 bedroom luxury Empire State VIEW
2.0-star property

2 bedroom luxury Empire State VIEW

Jul 13 - Jul 15

2 night stay

Dallas (DFW) to New York (JFK)

American Airlines • Coach

New York (JFK) to Dallas (DFW)

Frontier Airlines • Coach
Save 100% on your flight
Price was $2,694, price is now $1,362 per person
$1,362
per person
found 23 hours ago
Radio Hotel
4.0-star property

Radio Hotel

Sep 10 - Sep 14

4 night stay

Atlanta (ATL) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,220, price is now $633 per person
$633
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! (1,008 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! (156 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! (1,009 reviews)
"Comfortable bed, spacious room, nice walk-in shower, convenient location.. but watch out for cars speeding across drop-off area from the bus station across the street!"

Reviewed on Jul 6, 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 $82. 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 16 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 $82. 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 $82 and $655. 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.