Cheap Flights to Dutchess County from $50 (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 14 - Sun, Jan 17
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$98 Roundtrip, found 23 hours ago
$98
Roundtrip
found 23 hours ago
Select Allegiant Air flight, departing Thu, Jan 14 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Jan 17, priced at $98 found 23 hours ago
Thu, Jan 28 - Sun, Jan 31
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Thu, Jan 28 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Jan 31, priced at $100 found 2 days ago
Sat, Jan 16 - Sat, Jan 23
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$102 Roundtrip, found 20 hours ago
$102
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Sat, Jan 16 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Jan 23, priced at $102 found 20 hours ago
Thu, Jan 28 - Sun, Jan 31
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$107 Roundtrip, found 3 hours ago
$107
Roundtrip
found 3 hours ago
Select Allegiant Air flight, departing Thu, Jan 28 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Jan 31, priced at $107 found 3 hours ago
Thu, Jan 7 - Sun, Jan 17
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$109 Roundtrip, found 3 days ago
$109
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Thu, Jan 7 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Jan 17, priced at $109 found 3 days ago
Thu, Jan 21 - Sun, Jan 24
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$110 Roundtrip, found 2 days ago
$110
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Thu, Jan 21 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Jan 24, priced at $110 found 2 days ago
Thu, Jan 14 - Sun, Jan 17
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$113 Roundtrip, found 2 days ago
$113
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Thu, Jan 14 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Jan 17, priced at $113 found 2 days ago
Thu, Feb 4 - Sun, Feb 7
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$115 Roundtrip, found 3 hours ago
$115
Roundtrip
found 3 hours ago
Select Allegiant Air flight, departing Thu, Feb 4 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Feb 7, priced at $115 found 3 hours ago
Wed, Jan 6 - Sat, Jan 9
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$122 Roundtrip, found 3 hours ago
$122
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Wed, Jan 6 from Raleigh - Durham Intl. to Westchester County, returning Sat, Jan 9, priced at $122 found 3 hours ago
Mon, Dec 7 - Mon, Dec 14
SFB
Orlando Sanford Intl.
SWF
Stewart Intl.
$126 Roundtrip, found 3 days ago
$126
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Mon, Dec 7 from Orlando Sanford Intl. to Stewart Intl., returning Mon, Dec 14, priced at $126 found 3 days ago
OriginDestinationTravel DatesFlights From*
FLLNewburghJanuary 14 to January 17$98
PIENewburghJanuary 17 to January 24$124
MCOWest HarrisonJanuary 7 to January 12$154
MCONewburghJanuary 29 to February 6$154
RSWNewburghJanuary 30 to February 3$181
TPAWest HarrisonJanuary 7 to January 11$193
FLLWest HarrisonJanuary 29 to January 31$221
ATLWest HarrisonDecember 27 to January 1$279
DJTWest HarrisonDecember 8 to December 10$293
RSWWest HarrisonJanuary 8 to January 11$306
JAXWest HarrisonDecember 8 to December 15$347
ORDWest HarrisonDecember 19 to January 2$403
CLTWest HarrisonDecember 28 to December 30$420
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCONewburghNovember 13 to November 21$237
RSWNewburghNovember 14 to November 18$277
FLLNewburghNovember 15 to November 22$288
PIENewburghNovember 15 to November 22$343
JAXWest HarrisonNovember 14 to November 22$363
MCOWest HarrisonNovember 13 to November 16$396
TPAWest HarrisonNovember 14 to November 21$437
FLLWest HarrisonNovember 13 to November 16$520
DJTWest HarrisonNovember 15 to November 18$533
RSWWest HarrisonNovember 13 to November 17$534
ATLWest HarrisonNovember 14 to November 16$661
CLTWest HarrisonNovember 13 to November 17$800
ORDWest HarrisonNovember 13 to November 23$875
*Prices include taxes and fees

Best Dutchess County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Langham, New York, Fifth Avenue
5.0-star property

The Langham, New York, Fifth Avenue

Jan 8 - Jan 11

3 night stay

Atlanta (ATL) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Price was $1,420, price is now $812 per person
$812
per person
found 1 day ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Nov 19 - Nov 23

4 night stay

Los Angeles (LAX) to New Haven (HVN)

Alaska Airlines • Coach

New Haven (HVN) to Los Angeles (LAX)

JetBlue Airways • Coach
Save 100% on your flight
Price was $3,262, price is now $1,690 per person
$1,690
per person
found 2 hours ago
JW Marriott Essex House New York
4.5-star property

JW Marriott Essex House New York

Jan 20 - Jan 24

4 night stay

Atlanta (ATL) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Price was $1,529, price is now $888 per person
$888
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 Bananas Comedy Club and Casperkill Golf Club are located nearby.
9/10 Wonderful! (1,160 reviews)
"Clean room, comfy beds, and amazing breakfast (with vegan options!). Would stay again!"

Reviewed on Nov 9, 2026

Opens in a new windowHyatt Place Poughkeepsie / Hudson Valley
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
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! (1,009 reviews)
"There are a large selection of houses which make up the hotel (indeed, much of downtown Rhinebeck) and I would have benefitted from knowing more about the choices."

Reviewed on Nov 8, 2026

Opens in a new windowBeekman Arms and Delamater Inn
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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.
7.6/10 Good! (623 reviews)
"Room was uninhabitable."

Reviewed on Nov 8, 2026

Opens in a new windowQuality Inn Poughkeepsie
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 $98. 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 18 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 $98. 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 $98 and $875. 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.