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.

Thu, Jan 21 - Wed, Jan 27
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$82 Roundtrip, found 13 hours ago
$82
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Thu, Jan 21 from Raleigh - Durham Intl. to Westchester County, returning Wed, Jan 27, priced at $82 found 13 hours ago
Thu, Dec 3 - Sun, Dec 6
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$86 Roundtrip, just found
$86
Roundtrip
just found
Select Allegiant Air flight, departing Thu, Dec 3 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Dec 6, priced at $86 just found
Thu, Oct 22 - Sun, Oct 25
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$90 Roundtrip, found 3 hours ago
$90
Roundtrip
found 3 hours ago
Select Allegiant Air flight, departing Thu, Oct 22 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Oct 25, priced at $90 found 3 hours ago
Fri, Jan 15 - Sun, Jan 17
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$92 Roundtrip, found 2 days ago
$92
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jan 15 from Raleigh - Durham Intl. to Westchester County, returning Sun, Jan 17, priced at $92 found 2 days ago
Thu, Nov 12 - Sun, Nov 15
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$94 Roundtrip, just found
$94
Roundtrip
just found
Select Allegiant Air flight, departing Thu, Nov 12 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Nov 15, priced at $94 just found
Thu, Oct 1 - Sun, Oct 4
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$95 Roundtrip, found 3 hours ago
$95
Roundtrip
found 3 hours ago
Select Allegiant Air flight, departing Thu, Oct 1 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Oct 4, priced at $95 found 3 hours ago
Mon, Sep 21 - Wed, Sep 23
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$97 Roundtrip, found 3 days ago
$97
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Mon, Sep 21 from Raleigh - Durham Intl. to Westchester County, returning Wed, Sep 23, priced at $97 found 3 days ago
Sat, Sep 26 - Wed, Sep 30
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$108 Roundtrip, found 2 days ago
$108
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Sep 26 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Sep 30, priced at $108 found 2 days ago
OriginDestinationTravel DatesFlights From*
FLLNewburghOctober 1 to October 25$86
PIENewburghDecember 3 to December 10$117
MCONewburghSeptember 14 to September 19$148
MCOWest HarrisonOctober 24 to October 27$153
RSWNewburghSeptember 12 to September 26$188
DJTWest HarrisonOctober 27 to November 1$219
TPAWest HarrisonNovember 14 to November 16$221
FLLWest HarrisonNovember 6 to November 8$221
JAXWest HarrisonOctober 27 to November 4$239
CLTWest HarrisonDecember 3 to December 9$277
RSWWest HarrisonOctober 23 to October 27$277
ATLWest HarrisonSeptember 19 to September 23$312
ORDWest HarrisonOctober 23 to October 24$397
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
FLLNewburghAugust 30 to September 3$240
RSWNewburghAugust 29 to September 2$258
MCONewburghAugust 29 to September 5$307
PIENewburghAugust 30 to September 3$309
ORDWest HarrisonAugust 28 to September 1$402
FLLWest HarrisonAugust 28 to August 30$411
ATLWest HarrisonAugust 29 to September 19$451
RSWWest HarrisonAugust 29 to September 1$454
MCOWest HarrisonAugust 29 to September 1$467
TPAWest HarrisonAugust 30 to September 1$481
DJTWest HarrisonAugust 29 to August 30$489
CLTWest HarrisonAugust 28 to August 30$550
JAXWest HarrisonAugust 28 to September 6$574
*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!

Sep 3 - Sep 6

3 night stay

Atlanta (ATL) to New Haven (HVN)

Frontier Airlines • Roundtrip • Coach
Price was $2,295, price is now $1,077 per person
$1,077
per person
found 19 hours ago
Seven Beach Lane
2.0-star property

Seven Beach Lane

Oct 15 - Oct 20

5 night stay

San Juan (SJU) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $2,284, price is now $1,225 per person
$1,225
per person
found 1 day ago
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

Oct 27 - Nov 1

5 night stay

Atlanta (ATL) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Price was $4,330, price is now $2,340 per person
$2,340
per person
found 1 day ago
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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 Bananas Comedy Club are located nearby.
9/10 Wonderful! (1,050 reviews)
"Déjeuner vraiment bon et complet. Tout était bien les matelas de notre chambre était soso mais sinon tout était très bien"

Reviewed on Aug 22, 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.
8.2/10 Very Good! (984 reviews)
"Very nice walk through history in this gorgeous Inn. Centrally located and walkable to all the town has to offer. I loved the room - so nicely appointed - even included sherry! The towels even had a lavender smell to them which was a nice touch."

Reviewed on Aug 21, 2026

Opens in a new windowBeekman Arms and Delamater Inn
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! (1,014 reviews)
"No comments"

Reviewed on Aug 21, 2026

Opens in a new windowHoliday Inn Express Poughkeepsie by IHG
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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.
Opens in a new windowDoubleTree by Hilton Poughkeepsie Convention Center
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 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, January 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 $574. 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.