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

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.

Fri, Jan 1 - Thu, Jan 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$135 Roundtrip, found 5 hours ago
$135
Roundtrip
found 5 hours ago
Select Cape Air flight, departing Fri, Jan 1 from Logan Intl. to Lebanon Municipal, returning Thu, Jan 7, priced at $135 found 5 hours ago
Fri, Jan 1 - Thu, Jan 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$145 Roundtrip, found 5 hours ago
$145
Roundtrip
found 5 hours ago
Select Cape Air flight, departing Fri, Jan 1 from Logan Intl. to Lebanon Municipal, returning Thu, Jan 7, priced at $145 found 5 hours ago
Mon, Dec 14 - Mon, Dec 14
BOS
Logan Intl.
LEB
Lebanon Municipal
$150 Roundtrip, found 1 day ago
$150
Roundtrip
found 1 day ago
Select Cape Air flight, departing Mon, Dec 14 from Logan Intl. to Lebanon Municipal, returning Mon, Dec 14, priced at $150 found 1 day ago
Sun, Nov 1 - Wed, Nov 4
BOS
Logan Intl.
LEB
Lebanon Municipal
$155 Roundtrip, found 3 hours ago
$155
Roundtrip
found 3 hours ago
Select Cape Air flight, departing Sun, Nov 1 from Logan Intl. to Lebanon Municipal, returning Wed, Nov 4, priced at $155 found 3 hours ago
Thu, Nov 5 - Sun, Nov 8
BOS
Logan Intl.
LEB
Lebanon Municipal
$158 Roundtrip, found 5 days ago
$158
Roundtrip
found 5 days ago
Select Cape Air flight, departing Thu, Nov 5 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 8, priced at $158 found 5 days ago
Mon, Dec 14 - Mon, Dec 14
BOS
Logan Intl.
LEB
Lebanon Municipal
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Select Cape Air flight, departing Mon, Dec 14 from Logan Intl. to Lebanon Municipal, returning Mon, Dec 14, priced at $160 found 1 day ago
Fri, Jan 1 - Thu, Jan 7
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Select Cape Air flight, departing Fri, Jan 1 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Jan 7, priced at $160 found 1 day ago
Sun, Nov 1 - Wed, Nov 4
BOS
Logan Intl.
LEB
Lebanon Municipal
$165 Roundtrip, found 3 hours ago
$165
Roundtrip
found 3 hours ago
Select Cape Air flight, departing Sun, Nov 1 from Logan Intl. to Lebanon Municipal, returning Wed, Nov 4, priced at $165 found 3 hours ago
Fri, Jan 8 - Sat, Jan 9
HPN
Westchester County
LEB
Lebanon Municipal
$180 Roundtrip, found 9 hours ago
$180
Roundtrip
found 9 hours ago
Select Cape Air flight, departing Fri, Jan 8 from Westchester County to Lebanon Municipal, returning Sat, Jan 9, priced at $180 found 9 hours ago

Best Windsor County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Solitude Village at Okemo by Vail Resorts
4.0-star property

Solitude Village at Okemo by Vail Resorts

Oct 13 - Oct 17

4 night stay

Atlanta (ATL) to Springfield (VSF)

American Airlines • Coach

Springfield (VSF) to Atlanta (ATL)

Cape Air • Coach
Price was $1,481, price is now $1,394 per person
$1,394
per person
found 9 hours ago
The Suites at Killington Center
3.5-star property

The Suites at Killington Center

Oct 13 - Oct 17

4 night stay

Atlanta (ATL) to Rutland (RUT)

American Airlines • Coach

Rutland (RUT) to Atlanta (ATL)

Cape Air • Coach
Price was $1,596, price is now $1,429 per person
$1,429
per person
found 9 hours ago
Winterplace at Okemo, A Vail Resorts Property
4.0-star property

Winterplace at Okemo, A Vail Resorts Property

Oct 13 - Oct 17

4 night stay

Atlanta (ATL) to Springfield (VSF)

American Airlines • Coach

Springfield (VSF) to Atlanta (ATL)

Cape Air • Coach
Price was $1,584, price is now $1,484 per person
$1,484
per person
found 9 hours ago
Don't see what you're looking for?
See all available trips from Atlanta to Windsor County
View all trips

Frequently asked questions

How much is the cheapest flight to Windsor County?
A roundtrip flight to Windsor County cost as little as $135 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 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 $135. 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 $135 and $180. 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.