Cheap Flights to Dutchess County from $48 (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.

Sat, Nov 14 - Wed, Nov 18
MCO
Orlando Intl.
SWF
Stewart Intl.
$35 Roundtrip, found 5 days ago
$35
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Nov 14 from Orlando Intl. to Stewart Intl., returning Wed, Nov 18, priced at $35 found 5 days ago
Wed, Nov 11 - Wed, Nov 11
MCO
Orlando Intl.
SWF
Stewart Intl.
$40 Roundtrip, found 5 days ago
$40
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Stewart Intl., returning Wed, Nov 11, priced at $40 found 5 days ago
Wed, Nov 11 - Wed, Nov 11
MCO
Orlando Intl.
SWF
Stewart Intl.
$83 Roundtrip, found 5 days ago
$83
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Stewart Intl., returning Wed, Nov 11, priced at $83 found 5 days ago
Wed, Dec 16 - Wed, Jan 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$89 Roundtrip, found 5 days ago
$89
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Dec 16 from Orlando Intl. to Stewart Intl., returning Wed, Jan 6, priced at $89 found 5 days ago
Sat, Nov 21 - Tue, Dec 1
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$91 Roundtrip, found 5 days ago
$91
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Nov 21 from Raleigh - Durham Intl. to Westchester County, returning Tue, Dec 1, priced at $91 found 5 days ago
Thu, Jan 7 - Sun, Jan 17
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$96 Roundtrip, found 1 hour ago
$96
Roundtrip
found 1 hour ago
Select Allegiant Air flight, departing Thu, Jan 7 from Fort Lauderdale - Hollywood Intl. to Stewart Intl., returning Sun, Jan 17, priced at $96 found 1 hour ago
Sat, Dec 5 - Sat, Jan 23
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$102 Roundtrip, just found
$102
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Dec 5 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Jan 23, priced at $102 just found
Thu, Feb 11 - Sat, Feb 20
PIE
St. Petersburg-Clearwater Intl.
SWF
Stewart Intl.
$132 Roundtrip, found 3 days ago
$132
Roundtrip
found 3 days 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 days ago
OriginDestinationTravel DatesFlights From*
MCONewburghNovember 14 to November 18$35
FLLNewburghJanuary 7 to January 17$96
PIENewburghJanuary 7 to January 10$133
MCOWest HarrisonNovember 18 to November 23$176
RSWNewburghJanuary 9 to January 16$177
TPAWest HarrisonJanuary 22 to January 25$212
FLLWest HarrisonJanuary 8 to January 10$224
DJTWest HarrisonNovember 10 to November 14$227
RSWWest HarrisonJanuary 16 to January 25$294
ATLWest HarrisonNovember 14 to November 21$299
ORDWest HarrisonDecember 9 to December 16$307
JAXWest HarrisonNovember 17 to November 19$359
CLTWest HarrisonNovember 21 to November 25$476
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
FLLNewburghNovember 1 to November 22$127
MCONewburghNovember 1 to November 14$164
RSWNewburghOctober 31 to November 7$240
TPANewburghOctober 31 to November 2$311
ORDWest HarrisonOctober 30 to November 2$393
MCOWest HarrisonNovember 1 to November 5$425
TPAWest HarrisonOctober 31 to November 2$425
DJTWest HarrisonNovember 1 to November 9$482
RSWWest HarrisonOctober 30 to November 20$531
FLLWest HarrisonOctober 30 to November 2$597
ATLWest HarrisonOctober 30 to November 1$633
JAXWest HarrisonNovember 1 to November 2$1,089
*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!

Dec 8 - Dec 11

3 night stay

Dallas (DFW) to New Haven (HVN)

Southwest Airlines • Coach

New Haven (HVN) to Dallas (DFW)

Frontier Airlines • Coach
Price was $2,280, price is now $1,097 per person
$1,097
per person
found 1 day ago
Lotte New York Palace
4.5-star property

Lotte New York Palace

Dec 13 - Dec 17

4 night stay

Atlanta (ATL) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Price was $2,599, price is now $1,247 per person
$1,247
per person
found 1 day ago
Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

Dec 11 - Dec 14

3 night stay

Atlanta (ATL) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Price was $2,055, price is now $1,122 per person
$1,122
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! (1,144 reviews)
"The beds were terribly uncomfortable (lumpy) and the rooms were dingy,"

Reviewed on Oct 25, 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! (1,006 reviews)
"Room was run down but comfortable. Front desk was overwhelmed at check in and check out didn’t answer the phone during the day."

Reviewed on Oct 25, 2026

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.
9.2/10 Wonderful! (1,009 reviews)
"The hotel appeared clean but when I decided to take the stairs instead of the elevator I was met with a very dirty stairwell. It was very off putting. The headboard of the bed was also very dusty and doesn’t look like it gets cleaned regularly. The pillows were the worst I have ever encountered in ..."

Reviewed on Oct 26, 2026

Opens in a new windowComfort Suites Fishkill near Interstate 84
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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 (1,015 reviews)
"I really liked Mike he was very welcoming and helpful."

Reviewed on Oct 26, 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 $35. 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, November 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 $35. 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 $35 and $1,089. 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.