Flights To Dutchess County - Cheap Flights Starting at CA $72

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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 7 - Sun, Jan 10
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $145 Roundtrip, found 6 hours ago
CA $145
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Thu, Jan 7 from Raleigh - Durham Intl. to Westchester County, returning Sun, Jan 10, priced at CA $145 found 6 hours ago
Thu, Dec 3 - Mon, Dec 7
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $147 Roundtrip, found 3 days ago
CA $147
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Dec 3 from Raleigh - Durham Intl. to Westchester County, returning Mon, Dec 7, priced at CA $147 found 3 days ago
Wed, Dec 9 - Wed, Dec 16
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $152 Roundtrip, found 3 days ago
CA $152
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Dec 9 from Raleigh - Durham Intl. to Westchester County, returning Wed, Dec 16, priced at CA $152 found 3 days ago
Sat, Oct 31 - Sat, Nov 7
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
CA $187 Roundtrip, found 3 days ago
CA $187
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Oct 31 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Nov 7, priced at CA $187 found 3 days ago
Fri, Nov 6 - Mon, Nov 9
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $190 Roundtrip, found 6 days ago
CA $190
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Nov 6 from Raleigh - Durham Intl. to Westchester County, returning Mon, Nov 9, priced at CA $190 found 6 days ago
Sat, Oct 31 - Sat, Nov 7
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
CA $195 Roundtrip, found 7 hours ago
CA $195
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Sat, Oct 31 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Nov 7, priced at CA $195 found 7 hours ago
Sat, Oct 31 - Wed, Nov 4
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
CA $202 Roundtrip, found 3 days ago
CA $202
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Oct 31 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Nov 4, priced at CA $202 found 3 days ago
Tue, Nov 17 - Thu, Nov 19
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $217 Roundtrip, found 3 hours ago
CA $217
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Tue, Nov 17 from Raleigh - Durham Intl. to Westchester County, returning Thu, Nov 19, priced at CA $217 found 3 hours ago
Thu, Nov 5 - Sun, Nov 8
YYZ
Pearson Intl.
HPN
Westchester County
CA $491 Roundtrip, found 7 hours ago
CA $491
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Thu, Nov 5 from Pearson Intl. to Westchester County, returning Sun, Nov 8, priced at CA $491 found 7 hours ago
Sat, Oct 17 - Sat, Oct 24
YYZ
Pearson Intl.
HPN
Westchester County
CA $697 Roundtrip, found 2 days ago
CA $697
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Oct 17 from Pearson Intl. to Westchester County, returning Sat, Oct 24, priced at CA $697 found 2 days ago
Tue, Nov 17 - Mon, Nov 23
YYZ
Pearson Intl.
HPN
Westchester County
CA $817 Roundtrip, found 1 day ago
CA $817
Roundtrip
found 1 day ago
Select WestJet flight, departing Tue, Nov 17 from Pearson Intl. to Westchester County, returning Mon, Nov 23, priced at CA $817 found 1 day ago
OriginDestinationTravel datesFlights from*
MCONewburghDecember 3 to December 7CA $220
TPANewburghNovember 7 to November 14CA $241
MCOWest HarrisonNovember 6 to November 9CA $268
FLLWest HarrisonDecember 4 to December 6CA $345
DJTWest HarrisonNovember 10 to November 15CA $375
TPAWest HarrisonNovember 6 to November 9CA $398
RSWWest HarrisonOctober 26 to October 29CA $573
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
MCONewburghOctober 11 to October 17CA $441
*Prices include taxes and fees
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!

Nov 14 - Nov 17

3 night stay

Montreal (YUL) to New Haven (HVN)

Porter Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $3,263, price is now CA $1,837 per person
CA $1,837
per person
found 1 day ago
Lotte New York Palace
4.5-star property

Lotte New York Palace

Dec 7 - Dec 10

3 night stay

Halifax (YHZ) to New York (JFK)

Air Canada • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $4,703, price is now CA $2,607 per person
CA $2,607
per person
found 1 day ago
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

Dec 11 - Dec 15

4 night stay

Toronto (YTO) to New York (JFK)

Porter Airlines • Roundtrip • Coach
Save 100% on your flight
Price was CA $4,883, price is now CA $2,961 per person
CA $2,961
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Montreal to Dutchess County
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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.
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! (1,005 reviews)
"Cleen room"

Reviewed on Oct 8, 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.
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 (1,009 reviews)
"Put a "security hold" on my credit card which they wound up charging. This place is an utter dump and scammed my credit card as well."

Reviewed on Oct 7, 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 $145. 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, 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 CA $145. 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 $145 and CA $817. 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.