Flights To Windsor County - Cheap Flights Starting at CA $495

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Windsor County's top cities

A red convertible car parked in front of a brick house with black shutters and a white picket fence.

Woodstock

Flights
Woodstock

How Much Does it Cost To Fly To Windsor County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Mon, Jan 11 - Fri, Jan 22
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $906 Roundtrip, found 1 day ago
CA $906
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Jan 11 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Fri, Jan 22, priced at CA $906 found 1 day ago
Mon, Jan 11 - Fri, Jan 22
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $977 Roundtrip, found 1 day ago
CA $977
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Jan 11 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Fri, Jan 22, priced at CA $977 found 1 day ago
Mon, Jul 26 - Mon, Aug 23
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,034 Roundtrip, found 2 days ago
CA $1,034
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Jul 26 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Mon, Aug 23, priced at CA $1,034 found 2 days ago
Mon, Jan 11 - Fri, Jan 22
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,062 Roundtrip, found 1 day ago
CA $1,062
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Jan 11 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Fri, Jan 22, priced at CA $1,062 found 1 day ago
Mon, Jan 11 - Fri, Jan 22
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,069 Roundtrip, found 1 day ago
CA $1,069
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Jan 11 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Fri, Jan 22, priced at CA $1,069 found 1 day ago
Mon, Jan 11 - Fri, Jan 22
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,070 Roundtrip, found 1 day ago
CA $1,070
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Jan 11 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Fri, Jan 22, priced at CA $1,070 found 1 day ago
Mon, Jan 11 - Fri, Jan 22
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,077 Roundtrip, found 1 day ago
CA $1,077
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Jan 11 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Fri, Jan 22, priced at CA $1,077 found 1 day ago
Mon, Jan 11 - Fri, Jan 22
YUL
Pierre Elliott Trudeau Intl.
LEB
Lebanon Municipal
CA $1,078 Roundtrip, found 1 day ago
CA $1,078
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Jan 11 from Pierre Elliott Trudeau Intl. to Lebanon Municipal, returning Fri, Jan 22, priced at CA $1,078 found 1 day ago
Price found within the past 48 hours. Click for updated prices.
The Landgrove
3.5-star property

The Landgrove

Nov 19 - Nov 24

5 night stay

Edmonton (YEA) to Rutland (RUT)

United • Roundtrip • Coach
Price was CA $1,681, price is now CA $1,377 per person
CA $1,377
per person
found 14 hours ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0-star property

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Oct 23 - Oct 26

3 night stay

Montreal (YUL) to Rutland (RUT)

United • Non-stop roundtrip • Coach
Price was CA $1,622, price is now CA $1,411 per person
CA $1,411
per person
found 1 hour ago
Sinclair Inn Bed and Breakfast
4.0-star property

Sinclair Inn Bed and Breakfast

Nov 1 - Nov 5

4 night stay

Toronto (YYZ) to Springfield (VSF)

Delta • Non-stop roundtrip • Coach
Price was CA $1,645, price is now CA $1,473 per person
CA $1,473
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Edmonton to Windsor County
View all trips

Travelers ❤️ These Windsor County 🏨

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Quechee Gorge Bridge and Quechee Gorge Village are located nearby.
9.4/10 Exceptional! (1,376 reviews)
"Great room and nice staff. Good breakfast"

Reviewed on Oct 8, 2026

Opens in a new windowAlign Inn Vermont
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
9.4/10 Exceptional! (615 reviews)
"Lovely feel to the hotel with friendly staff. Room was comfortable and location is excellent. Love Woodstock as a destination. I am never the biggest fan of breakfast, but really enjoyed it for once"

Reviewed on Oct 7, 2026

Opens in a new windowWoodstock Inn & Resort
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
111 Jackson Gore Road Ludlow VT
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Timber Ripper Mountain Coaster are located nearby.
8.6/10 Excellent! (916 reviews)
"Everything about this property was exceptional, EXCEPT the bed. We had an amazing time, enjoyed the lift to view fall colors & mountain coaster. But we had a miserable experience sleeping. The beds are like rock. I know it's the granite state, but get some toppers!"

Reviewed on Oct 6, 2026

Opens in a new windowJackson Gore Village, A Vail Resorts Property
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast in our reviews. Popular attractions Union Arena Community Center and Five Elm Arches are located nearby.
Opens in a new windowThe Jackson
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 Windsor County?
A roundtrip flight to Windsor County cost as little as CA $906 over the last seven days. Once you've selected your travel dates, we'll help you score an amazing deal. This price was available on Travelocity for flights to Windsor County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Windsor County?
There are 15 airlines with flights to Windsor County. If you're thinking about a journey to Chester, opt for Cape Air. This leading carrier operates roughly 91 services per month to Windsor County's main city.
What is the cheapest month to fly to Windsor County?
For the best chance at snapping up a great flight deal, organize your break sometime during January. Based on Travelocity's direct flight demand from January to December last year, it's the most affordable time to hop on a plane to Windsor County.
How can I check my flight status to Windsor County?
Get helpful alerts about your flight status, gate number changes and more with Trips. This handy Travelocity portal is located at the top of our homepage and is the place to view and manage your bookings. Sign in to your account or create a new one in a matter of seconds and you're good to go. You can also use the Travelocity app to see the details of your flight to Windsor County while you're on the move — and even while you're offline. Travelocity's app has all your booking needs covered. Whether you want to organize a shuttle from your airport or share itineraries with any members of your family flying with you, the app is your one-stop travel shop.
How do I find the best deals on flights to Windsor County?
Being flexible with your travel dates will help you grab a fantastic deal. Travelocity makes it super simple to find your ideal fare through the "Flexible dates" feature. Search for your Windsor County flight, then compare the cheapest prices for nearby dates by clicking the Flexible dates box above. Booking early and flying outside of busy periods are other things to consider. In the last seven days, the lowest price for a roundtrip flight to Windsor County was CA $906. 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 Windsor County with Travelocity?
If you're seeking cheap flights to Windsor County, you'll discover some great deals with Travelocity. From cheap family flights with low-cost air carriers to flexible ticket options, we can help you out. Experience a worry-free break with our round-the-clock customer assistance, Price Match Guarantee and free cancellations with most hotels. Start packing your suitcase and get set to jet off to this fabulous destination.
How much is a flight to Windsor County on average?
Based on prices found on Travelocity over the last seven days, roundtrip flights to Windsor County were between CA $906 and CA $1,078. Whenever you're ready to take off, Travelocity will help you find a fare that'll match 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.