Flights To Windsor County - Cheap Flights Starting at CA $800

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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, Jun 11 - Sun, Jun 14
MSP
Minneapolis - St. Paul Intl.
RUT
Rutland Southern Vermont Regional
CA $1,152 Roundtrip, found 21 hours ago
CA $1,152
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Thu, Jun 11 from Minneapolis - St. Paul Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 14, priced at CA $1,152 found 21 hours ago
Thu, Jun 11 - Sun, Jun 14
MSP
Minneapolis - St. Paul Intl.
RUT
Rutland Southern Vermont Regional
CA $1,168 Roundtrip, found 21 hours ago
CA $1,168
Roundtrip
found 21 hours ago
Select Delta flight, departing Thu, Jun 11 from Minneapolis - St. Paul Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 14, priced at CA $1,168 found 21 hours ago
Thu, Jun 11 - Sun, Jun 14
MSP
Minneapolis - St. Paul Intl.
RUT
Rutland Southern Vermont Regional
CA $1,174 Roundtrip, found 21 hours ago
CA $1,174
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Thu, Jun 11 from Minneapolis - St. Paul Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 14, priced at CA $1,174 found 21 hours ago
Thu, Jun 11 - Sun, Jun 14
MSP
Minneapolis - St. Paul Intl.
RUT
Rutland Southern Vermont Regional
CA $1,182 Roundtrip, found 21 hours ago
CA $1,182
Roundtrip
found 21 hours ago
Select Delta flight, departing Thu, Jun 11 from Minneapolis - St. Paul Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 14, priced at CA $1,182 found 21 hours ago
Thu, Jun 11 - Sun, Jun 14
MSP
Minneapolis - St. Paul Intl.
RUT
Rutland Southern Vermont Regional
CA $1,189 Roundtrip, found 21 hours ago
CA $1,189
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Thu, Jun 11 from Minneapolis - St. Paul Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 14, priced at CA $1,189 found 21 hours ago
Thu, Jun 11 - Sun, Jun 14
MSP
Minneapolis - St. Paul Intl.
RUT
Rutland Southern Vermont Regional
CA $1,196 Roundtrip, found 21 hours ago
CA $1,196
Roundtrip
found 21 hours ago
Select Delta flight, departing Thu, Jun 11 from Minneapolis - St. Paul Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 14, priced at CA $1,196 found 21 hours ago
Thu, Jun 11 - Sun, Jun 14
MSP
Minneapolis - St. Paul Intl.
RUT
Rutland Southern Vermont Regional
CA $1,210 Roundtrip, found 21 hours ago
CA $1,210
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Thu, Jun 11 from Minneapolis - St. Paul Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 14, priced at CA $1,210 found 21 hours ago
Thu, Jun 11 - Sun, Jun 14
MSP
Minneapolis - St. Paul Intl.
RUT
Rutland Southern Vermont Regional
CA $1,211 Roundtrip, found 21 hours ago
CA $1,211
Roundtrip
found 21 hours ago
Select Delta flight, departing Thu, Jun 11 from Minneapolis - St. Paul Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 14, priced at CA $1,211 found 21 hours ago

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! (1,199 reviews)
"There were some issues with the layout of the room, namely that the bathroom and the kitchen share the same space! There was a main room with beds, tv and chairs (no problems in this room), and then a dividing barn door. On the other side of the barn door was a sink. To the right of the sink was ..."

Reviewed on May 27, 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! (580 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."

Reviewed on May 22, 2026

Opens in a new windowWoodstock Inn & Resort
Hotel Coolidge

Hotel Coolidge

3 out of 5
39 South Main Street White River Junction VT
Book a stay at this business-friendly hotel in White River Junction. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Briggs Opera House and Barrette Center for the Arts are located nearby.
8.2/10 Very Good! (1,001 reviews)
"Breakfast was amazing and the room was very comfortable."

Reviewed on May 26, 2026

Opens in a new windowHotel Coolidge
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The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
8.8/10 Excellent! (931 reviews)
"Yes"

Reviewed on May 18, 2026

Opens in a new windowThe Shire Woodstock
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 $1,152 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 June. 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 $1,152. 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 $1,152 and CA $1,211. 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.