Flights To Dutchess County - Cheap Flights Starting at CA $300

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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.

Mon, Jul 20 - Mon, Jul 27
YYZ
Pearson Intl.
HPN
Westchester County
CA $510 Roundtrip, found 1 day ago
CA $510
Roundtrip
found 1 day ago
Select WestJet flight, departing Mon, Jul 20 from Pearson Intl. to Westchester County, returning Mon, Jul 27, priced at CA $510 found 1 day ago
Fri, Jun 12 - Sun, Jun 14
YYZ
Pearson Intl.
HPN
Westchester County
CA $541 Roundtrip, found 2 days ago
CA $541
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Jun 12 from Pearson Intl. to Westchester County, returning Sun, Jun 14, priced at CA $541 found 2 days ago
Tue, Aug 4 - Sat, Aug 8
YYZ
Pearson Intl.
HPN
Westchester County
CA $543 Roundtrip, found 2 days ago
CA $543
Roundtrip
found 2 days ago
Select WestJet flight, departing Tue, Aug 4 from Pearson Intl. to Westchester County, returning Sat, Aug 8, priced at CA $543 found 2 days ago
Sat, May 30 - Tue, Jun 9
YYZ
Pearson Intl.
HPN
Westchester County
CA $560 Roundtrip, found 1 day ago
CA $560
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, May 30 from Pearson Intl. to Westchester County, returning Tue, Jun 9, priced at CA $560 found 1 day ago
Sat, Jun 6 - Sat, Jun 13
YYZ
Pearson Intl.
HPN
Westchester County
CA $576 Roundtrip, found 1 day ago
CA $576
Roundtrip
found 1 day ago
Select WestJet flight, departing Sat, Jun 6 from Pearson Intl. to Westchester County, returning Sat, Jun 13, priced at CA $576 found 1 day ago
Sat, Jun 27 - Wed, Jul 8
YYZ
Pearson Intl.
HPN
Westchester County
CA $577 Roundtrip, found 6 days ago
CA $577
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Jun 27 from Pearson Intl. to Westchester County, returning Wed, Jul 8, priced at CA $577 found 6 days ago
Mon, Jul 20 - Mon, Jul 27
YYZ
Pearson Intl.
HPN
Westchester County
CA $578 Roundtrip, found 1 day ago
CA $578
Roundtrip
found 1 day ago
Select WestJet flight, departing Mon, Jul 20 from Pearson Intl. to Westchester County, returning Mon, Jul 27, priced at CA $578 found 1 day ago
Sat, Jun 27 - Wed, Jul 8
YYZ
Pearson Intl.
HPN
Westchester County
CA $580 Roundtrip, found 6 days ago
CA $580
Roundtrip
found 6 days ago
Select WestJet flight, departing Sat, Jun 27 from Pearson Intl. to Westchester County, returning Wed, Jul 8, priced at CA $580 found 6 days ago
OriginDestinationTravel datesFlights from*
MCOWest HarrisonJuly 29 to August 1CA $214
MCONewburghAugust 27 to August 30CA $253
PBIWest HarrisonJune 17 to June 23CA $263
TPAWest HarrisonJuly 23 to July 27CA $277
TPANewburghJune 10 to June 13CA $291
FLLWest HarrisonJune 16 to June 22CA $327
RSWNewburghAugust 19 to August 21CA $362
RSWWest HarrisonAugust 20 to August 21CA $375
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
MCONewburghMay 29 to May 31CA $262
RSWWest HarrisonMay 29 to June 4CA $501
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.
Topping Rose House
4.5-star property

Topping Rose House

Jul 5 - Jul 8

3 night stay

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

Delta • Roundtrip • Coach
Price was CA $2,752, price is now CA $1,717 per person
CA $1,717
per person
found 1 day ago
Mandarin Oriental, New York
5.0-star property

Mandarin Oriental, New York

Jun 10 - Jun 13

3 night stay

Toronto (YYZ) to New York (JFK)

Porter Airlines • Roundtrip • Coach
Price was CA $5,088, price is now CA $3,089 per person
CA $3,089
per person
found 1 day ago
Hotel Riu Plaza Manhattan Times Square
4.0-star property

Hotel Riu Plaza Manhattan Times Square

Jun 26 - Jul 3

7 night stay

Winnipeg (YWG) to New York (JFK)

Air Canada • Non-stop • Coach

New York (JFK) to Winnipeg (YWG)

United • Non-stop • Coach
Price was CA $3,794, price is now CA $2,397 per person
CA $2,397
per person
found 1 day 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 (1,002 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! (1,002 reviews)
"Good breakfast, clean hotel, and great staff."

Reviewed on May 22, 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! (104 reviews)
"Perfectly good place for a short stay."

Reviewed on May 23, 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 (959 reviews)
"There was no stay. Was told there was no availability. Not happy with the experience at all."

Reviewed on May 23, 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 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, 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.