Flights To Dutchess County - Cheap Flights Starting at CA $87

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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.

Wed, Jul 29 - Sat, Aug 1
MCO
Orlando Intl.
HPN
Westchester County
CA $214 Roundtrip, found 5 days ago
CA $214
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Jul 29 from Orlando Intl. to Westchester County, returning Sat, Aug 1, priced at CA $214 found 5 days ago
Thu, Jun 11 - Sat, Jun 13
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $237 Roundtrip, found 2 days ago
CA $237
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jun 11 from Orlando Intl. to Stewart Intl., returning Sat, Jun 13, priced at CA $237 found 2 days ago
Wed, Jul 29 - Tue, Aug 4
MCO
Orlando Intl.
HPN
Westchester County
CA $238 Roundtrip, found 6 days ago
CA $238
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Jul 29 from Orlando Intl. to Westchester County, returning Tue, Aug 4, priced at CA $238 found 6 days ago
Thu, Sep 17 - Wed, Sep 23
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $242 Roundtrip, found 12 hours ago
CA $242
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Thu, Sep 17 from Orlando Intl. to Stewart Intl., returning Wed, Sep 23, priced at CA $242 found 12 hours ago
Wed, Jul 29 - Sat, Aug 1
MCO
Orlando Intl.
HPN
Westchester County
CA $248 Roundtrip, found 5 days ago
CA $248
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Wed, Jul 29 from Orlando Intl. to Westchester County, returning Sat, Aug 1, priced at CA $248 found 5 days ago
Tue, Jun 23 - Tue, Jul 14
MCO
Orlando Intl.
HPN
Westchester County
CA $250 Roundtrip, found 5 days ago
CA $250
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Tue, Jun 23 from Orlando Intl. to Westchester County, returning Tue, Jul 14, priced at CA $250 found 5 days ago
Thu, Aug 27 - Sun, Aug 30
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $253 Roundtrip, found 3 days ago
CA $253
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Aug 27 from Orlando Intl. to Stewart Intl., returning Sun, Aug 30, priced at CA $253 found 3 days ago
Thu, Jun 4 - Sat, Jun 6
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $253 Roundtrip, found 2 days ago
CA $253
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jun 4 from Orlando Intl. to Stewart Intl., returning Sat, Jun 6, priced at CA $253 found 2 days ago
Mon, Jun 8 - Sat, Jun 13
YYZ
Pearson Intl.
HPN
Westchester County
CA $401 Roundtrip, found 2 days ago
CA $401
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Jun 8 from Pearson Intl. to Westchester County, returning Sat, Jun 13, priced at CA $401 found 2 days ago
Mon, Jun 8 - Sat, Jun 13
YYZ
Pearson Intl.
HPN
Westchester County
CA $479 Roundtrip, found 2 days ago
CA $479
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Jun 8 from Pearson Intl. to Westchester County, returning Sat, Jun 13, priced at CA $479 found 2 days ago
Mon, Jun 8 - Sat, Jun 13
YYZ
Pearson Intl.
HPN
Westchester County
CA $484 Roundtrip, found 2 days ago
CA $484
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Jun 8 from Pearson Intl. to Westchester County, returning Sat, Jun 13, priced at CA $484 found 2 days ago
OriginDestinationTravel datesFlights from*
MCOWest HarrisonJuly 29 to August 1CA $214
MCONewburghJune 11 to June 13CA $237
TPAWest HarrisonAugust 21 to August 24CA $249
PBIWest HarrisonJuly 21 to July 23CA $271
TPANewburghJune 10 to June 13CA $291
FLLWest HarrisonJuly 27 to August 4CA $333
RSWNewburghAugust 19 to August 21CA $362
RSWWest HarrisonAugust 20 to August 21CA $375
ATLWest HarrisonJuly 1 to July 19CA $543
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
TPAWest HarrisonMay 29 to June 1CA $583
FLLWest HarrisonMay 31 to June 1CA $911
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
New York Marriott Marquis
4.5-star property

New York Marriott Marquis

Jun 30 - Jul 3

3 night stay

Buffalo (BUF) to Newark Liberty Intl. Airport (EWR)

American Airlines • Coach

Newark Liberty Intl. Airport (EWR) to Buffalo (BUF)

Delta • Coach
Price was CA $1,559, price is now CA $891 per person
CA $891
per person
found 1 day ago
The Towers at Lotte New York Palace
5.0-star property

The Towers at Lotte New York Palace

Jul 12 - Jul 15

3 night stay

Buffalo (BUF) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Price was CA $3,309, price is now CA $1,745 per person
CA $1,745
per person
found 1 day ago
Topping Rose House
4.5-star property

Topping Rose House

Jul 12 - Jul 15

3 night stay

Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)

Porter Airlines • Roundtrip • Coach
Price was CA $2,781, price is now CA $1,699 per person
CA $1,699
per person
found 17 hours ago
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Travelers ❤️ These Dutchess County 🏨

Studio 6 Extended Stay Fishkill Route 9 NY

Studio 6 Extended Stay Fishkill Route 9 NY

2.5 out of 5
25 Merritt Blvd Fishkill NY
Stay at this hotel in Fishkill. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Van Wyck Homestead Museum and Fishkill Golf Course are located nearby.
6.6/10 (1,001 reviews)
"Was not able to stay there due to accommodations. It’s a good thing though. The place smelt like dog urine and looked run down. Still waiting on my refund and it’s been 5 days."

Reviewed on May 19, 2026

Opens in a new windowStudio 6 Extended Stay Fishkill Route 9 NY
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 WiFi, free parking, and breakfast (surcharge). 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! (1,007 reviews)
"If you stay here make sure they don’t put you on the 1st floor. My family and I will never be staying at this hotel again. We were put on the 1st floor and our room floor had water coming up from the seems everywhere. I told the front desk and the man there came to see and gave me extra towels to ..."

Reviewed on May 26, 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 Fishkill Golf Course are located nearby.
8.2/10 Very Good! (109 reviews)
"Nothing fancy, no frills. cold breakfast"

Reviewed on May 26, 2026

Opens in a new windowSpark by Hilton Fishkill
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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 Blodgett Memorial Library and Van Wyck Homestead Museum are located nearby.
6.2/10 (964 reviews)
"We showed up for our reservation and we're told they overbooked and we did not have a room. The staff indicated we were on our own to find a new place to stay."

Reviewed on May 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 CA $214. 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 20 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, July 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 CA $214. 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 CA $214 and CA $911. 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.