Cheap Flights to Windsor County from $76 (2026/2027)

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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.

Sun, Nov 1 - Sat, Nov 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$155 Roundtrip, found 15 hours ago
$155
Roundtrip
found 15 hours ago
Select Cape Air flight, departing Sun, Nov 1 from Logan Intl. to Lebanon Municipal, returning Sat, Nov 7, priced at $155 found 15 hours ago
Sun, Nov 1 - Sat, Nov 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$165 Roundtrip, found 15 hours ago
$165
Roundtrip
found 15 hours ago
Select Cape Air flight, departing Sun, Nov 1 from Logan Intl. to Lebanon Municipal, returning Sat, Nov 7, priced at $165 found 15 hours ago
Mon, Oct 19 - Mon, Oct 19
BOS
Logan Intl.
LEB
Lebanon Municipal
$170 Roundtrip, found 23 hours ago
$170
Roundtrip
found 23 hours ago
Select Cape Air flight, departing Mon, Oct 19 from Logan Intl. to Lebanon Municipal, returning Mon, Oct 19, priced at $170 found 23 hours ago
Mon, Oct 19 - Mon, Oct 19
BOS
Logan Intl.
LEB
Lebanon Municipal
$175 Roundtrip, found 23 hours ago
$175
Roundtrip
found 23 hours ago
Select Cape Air flight, departing Mon, Oct 19 from Logan Intl. to Lebanon Municipal, returning Mon, Oct 19, priced at $175 found 23 hours ago
Mon, Aug 17 - Sat, Aug 22
BOS
Logan Intl.
LEB
Lebanon Municipal
$178 Roundtrip, found 2 hours ago
$178
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Mon, Aug 17 from Logan Intl. to Lebanon Municipal, returning Sat, Aug 22, priced at $178 found 2 hours ago
Mon, Oct 19 - Mon, Oct 19
BOS
Logan Intl.
LEB
Lebanon Municipal
$180 Roundtrip, found 23 hours ago
$180
Roundtrip
found 23 hours ago
Select Cape Air flight, departing Mon, Oct 19 from Logan Intl. to Lebanon Municipal, returning Mon, Oct 19, priced at $180 found 23 hours ago
Fri, Oct 16 - Sun, Oct 18
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 12 hours ago
$180
Roundtrip
found 12 hours ago
Select Cape Air flight, departing Fri, Oct 16 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Oct 18, priced at $180 found 12 hours ago
Fri, Sep 11 - Thu, Sep 17
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$183 Roundtrip, found 1 hour ago
$183
Roundtrip
found 1 hour ago
Select Cape Air flight, departing Fri, Sep 11 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Sep 17, priced at $183 found 1 hour ago
Mon, Sep 21 - Sat, Sep 26
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$334 Roundtrip, found 15 hours ago
$334
Roundtrip
found 15 hours ago
Select Delta flight, departing Mon, Sep 21 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $334 found 15 hours ago

Best Windsor County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village, A Vail Resorts Property
3.0-star property

Jackson Gore Village, A Vail Resorts Property

Oct 7 - Oct 12

5 night stay

Minneapolis (MSP) to Springfield (VSF)

American Airlines • Coach

Springfield (VSF) to Minneapolis (MSP)

Cape Air • Coach
Price was $1,244, price is now $1,066 per person
$1,066
per person
found 1 day ago
Okemo Mountain Lodging by Vail Resorts
3.5-star property

Okemo Mountain Lodging by Vail Resorts

Oct 7 - Oct 12

5 night stay

Minneapolis (MSP) to Springfield (VSF)

American Airlines • Coach

Springfield (VSF) to Minneapolis (MSP)

Cape Air • Coach
Price was $1,542, price is now $1,313 per person
$1,313
per person
found 1 day ago
Winterplace at Okemo, A Vail Resorts Property
4.0-star property

Winterplace at Okemo, A Vail Resorts Property

Oct 7 - Oct 12

5 night stay

Minneapolis (MSP) to Springfield (VSF)

American Airlines • Coach

Springfield (VSF) to Minneapolis (MSP)

Cape Air • Coach
Price was $1,456, price is now $1,249 per person
$1,249
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.
9.4/10 Exceptional! (1,285 reviews)
"It is a great location with shops and restaurants within walking distance and Quechee Gorge. The hotel is very clean, great breakfast and wonderful calm, quiet and friendly atmosphere. atmosphere."

Reviewed on Aug 14, 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 Quechee Gorge Bridge and Middle Covered Bridge 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! (863 reviews)
"Perfect"

Reviewed on Aug 7, 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! (1,008 reviews)
"Everything was good I cannot complain"

Reviewed on Aug 12, 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 $155 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 16 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 November. 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 $155. 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 $155 and $334. 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.
What can I expect on a flight to Windsor County?
If you have a long-haul flight to Windsor County, you can usually expect drinks, food and entertainment to be included. Airlines endeavor to make longer flights as comfortable as they can. Shorter trips — as well as flights offered by budget airlines — may not come with such inclusions. If you're on the lookout for cheap flights for family vacations with a budget carrier, you'll usually have to pay extra for meals and entertainment.