Flights To Windsor County - Cheap Flights Starting at CA $581

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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.

Thu, Oct 15 - Sun, Oct 18
OMA
Eppley Field
LEB
Lebanon Municipal
CA $1,234 Roundtrip, found 16 hours ago
CA $1,234
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Thu, Oct 15 from Eppley Field to Lebanon Municipal, returning Sun, Oct 18, priced at CA $1,234 found 16 hours ago
Thu, Oct 15 - Sun, Oct 18
OMA
Eppley Field
LEB
Lebanon Municipal
CA $1,256 Roundtrip, found 16 hours ago
CA $1,256
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Thu, Oct 15 from Eppley Field to Lebanon Municipal, returning Sun, Oct 18, priced at CA $1,256 found 16 hours ago
Thu, Oct 15 - Sun, Oct 18
OMA
Eppley Field
LEB
Lebanon Municipal
CA $1,379 Roundtrip, found 16 hours ago
CA $1,379
Roundtrip
found 16 hours ago
Select Delta flight, departing Thu, Oct 15 from Eppley Field to Lebanon Municipal, returning Sun, Oct 18, priced at CA $1,379 found 16 hours ago
Thu, Oct 15 - Sun, Oct 18
OMA
Eppley Field
LEB
Lebanon Municipal
CA $1,399 Roundtrip, found 16 hours ago
CA $1,399
Roundtrip
found 16 hours ago
Select Delta flight, departing Thu, Oct 15 from Eppley Field to Lebanon Municipal, returning Sun, Oct 18, priced at CA $1,399 found 16 hours ago
Thu, Oct 15 - Sun, Oct 18
OMA
Eppley Field
LEB
Lebanon Municipal
CA $1,468 Roundtrip, found 16 hours ago
CA $1,468
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Thu, Oct 15 from Eppley Field to Lebanon Municipal, returning Sun, Oct 18, priced at CA $1,468 found 16 hours ago
Thu, Oct 15 - Sun, Oct 18
OMA
Eppley Field
LEB
Lebanon Municipal
CA $1,491 Roundtrip, found 16 hours ago
CA $1,491
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Thu, Oct 15 from Eppley Field to Lebanon Municipal, returning Sun, Oct 18, priced at CA $1,491 found 16 hours ago
Thu, Oct 15 - Sun, Oct 18
OMA
Eppley Field
LEB
Lebanon Municipal
CA $1,596 Roundtrip, found 16 hours ago
CA $1,596
Roundtrip
found 16 hours ago
Select Delta flight, departing Thu, Oct 15 from Eppley Field to Lebanon Municipal, returning Sun, Oct 18, priced at CA $1,596 found 16 hours ago
Thu, Oct 15 - Sun, Oct 18
OMA
Eppley Field
LEB
Lebanon Municipal
CA $1,602 Roundtrip, found 16 hours ago
CA $1,602
Roundtrip
found 16 hours ago
Select Delta flight, departing Thu, Oct 15 from Eppley Field to Lebanon Municipal, returning Sun, Oct 18, priced at CA $1,602 found 16 hours ago
Price found within the past 48 hours. Click for updated prices.
My Place Hotel-Randolph VT
2.0-star property

My Place Hotel-Randolph VT

Oct 2 - Oct 4

2 night stay

Toronto (YYZ) to Rutland (RUT)

United • Non-stop roundtrip • Coach
Price was CA $1,255, price is now CA $1,106 per person
CA $1,106
per person
found 1 day ago
Castle Hill Resort And Spa
3.5-star property

Castle Hill Resort And Spa

Sep 4 - Sep 6

2 night stay

Toronto (YYZ) to Rutland (RUT)

WestJet • Non-stop roundtrip • Coach
Price was CA $1,418, price is now CA $1,257 per person
CA $1,257
per person
found 1 day ago
Latchis Hotel
2.5-star property

Latchis Hotel

Sep 4 - Sep 6

2 night stay

Toronto (YYZ) to Springfield (VSF)

WestJet • Non-stop roundtrip • Coach
Price was CA $1,352, price is now CA $1,208 per person
CA $1,208
per person
found 1 day ago
Don't see what you're looking for?
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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.
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! (599 reviews)
"Amazing! Will visit again."

Reviewed on Aug 7, 2026

Opens in a new windowWoodstock Inn & Resort
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
485 Hotel Road Brownsville VT
Stay at this resort in Brownsville. Enjoy a business center, a fireplace in the lobby, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions Mount Ascutney and Mt Ascutney State Park are located nearby.
9/10 Wonderful! (868 reviews)
"The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus."

Reviewed on Aug 22, 2026

Opens in a new windowHoliday Inn Club Vacations Mount Ascutney Resort by IHG
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On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Union Arena Community Center and Five Elm Arches are located nearby.
9.4/10 Exceptional! (1,011 reviews)
"Staff was friendly and the room was clean. Nice social atmosphere, game rooms."

Reviewed on Aug 20, 2026

Opens in a new windowOn The River Inn
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 $1,234 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 October. 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 $1,234. 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 $1,234 and CA $1,602. 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.