Flights To Windsor County - Cheap Flights Starting at CA $124

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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.

Fri, Sep 4 - Tue, Sep 8
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $261 Roundtrip, found 2 days ago
CA $261
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Sep 4 from Logan Intl. to Lebanon Municipal, returning Tue, Sep 8, priced at CA $261 found 2 days ago
Fri, Sep 4 - Tue, Sep 8
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $275 Roundtrip, found 2 days ago
CA $275
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Sep 4 from Logan Intl. to Lebanon Municipal, returning Tue, Sep 8, priced at CA $275 found 2 days ago
Thu, Sep 3 - Tue, Sep 8
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
CA $280 Roundtrip, found 7 hours ago
CA $280
Roundtrip
found 7 hours ago
Select Cape Air flight, departing Thu, Sep 3 from Logan Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 8, priced at CA $280 found 7 hours ago
Fri, Sep 4 - Tue, Sep 8
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $289 Roundtrip, found 2 days ago
CA $289
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Sep 4 from Logan Intl. to Lebanon Municipal, returning Tue, Sep 8, priced at CA $289 found 2 days ago
Thu, Sep 3 - Tue, Sep 8
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
CA $293 Roundtrip, found 7 hours ago
CA $293
Roundtrip
found 7 hours ago
Select Cape Air flight, departing Thu, Sep 3 from Logan Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 8, priced at CA $293 found 7 hours ago
Fri, Sep 4 - Tue, Sep 8
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $303 Roundtrip, found 2 days ago
CA $303
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Sep 4 from Logan Intl. to Lebanon Municipal, returning Tue, Sep 8, priced at CA $303 found 2 days ago
Thu, Sep 3 - Tue, Sep 8
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
CA $307 Roundtrip, found 7 hours ago
CA $307
Roundtrip
found 7 hours ago
Select Cape Air flight, departing Thu, Sep 3 from Logan Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 8, priced at CA $307 found 7 hours ago
Fri, Sep 4 - Tue, Sep 8
BOS
Logan Intl.
LEB
Lebanon Municipal
CA $317 Roundtrip, found 2 days ago
CA $317
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Sep 4 from Logan Intl. to Lebanon Municipal, returning Tue, Sep 8, priced at CA $317 found 2 days ago
Price found within the past 48 hours. Click for updated prices.
Latchis Hotel
2.5-star property

Latchis Hotel

Sep 4 - Sep 7

3 night stay

Rochester (ROC) to Springfield (VSF)

American Airlines • Non-stop • Coach

Springfield (VSF) to Rochester (ROC)

Delta • Non-stop • Coach
Price was CA $1,137, price is now CA $986 per person
CA $986
per person
found 1 day ago
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 4 hours ago
Deerfield Valley Inn
2.0-star property

Deerfield Valley Inn

Oct 9 - Oct 12

3 night stay

Toronto (YTO) to Springfield (VSF)

United • Non-stop roundtrip • Coach
Price was CA $1,346, price is now CA $1,209 per person
CA $1,209
per person
found 14 hours ago
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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.
9.4/10 Exceptional! (1,297 reviews)
"Excellent quiet location for a relaxing vacation. Housekeeping and other staff were pleasant. Disappointed there was no dresser or closet for 2 people to unpack our clothing for a full week stay"

Reviewed on Aug 22, 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! (598 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 $261 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 11 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 September. 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 $261. 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 $261 and CA $317. 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.