Cheap Flights to Windsor County from $77 (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, just found
$155
Roundtrip
just found
Select Cape Air flight, departing Sun, Nov 1 from Logan Intl. to Lebanon Municipal, returning Sat, Nov 7, priced at $155 just found
Sun, Nov 1 - Sat, Nov 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$165 Roundtrip, just found
$165
Roundtrip
just found
Select Cape Air flight, departing Sun, Nov 1 from Logan Intl. to Lebanon Municipal, returning Sat, Nov 7, priced at $165 just found
Mon, Oct 19 - Mon, Oct 19
BOS
Logan Intl.
LEB
Lebanon Municipal
$170 Roundtrip, found 6 days ago
$170
Roundtrip
found 6 days ago
Select Cape Air flight, departing Mon, Oct 19 from Logan Intl. to Lebanon Municipal, returning Mon, Oct 19, priced at $170 found 6 days ago
Wed, Nov 25 - Sun, Nov 29
BOS
Logan Intl.
LEB
Lebanon Municipal
$175 Roundtrip, found 3 days ago
$175
Roundtrip
found 3 days ago
Select Cape Air flight, departing Wed, Nov 25 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 29, priced at $175 found 3 days ago
Fri, Oct 16 - Sun, Oct 18
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 6 days ago
$180
Roundtrip
found 6 days 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 6 days ago
Fri, Feb 12 - Mon, Feb 15
HPN
Westchester County
LEB
Lebanon Municipal
$200 Roundtrip, found 2 days ago
$200
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Feb 12 from Westchester County to Lebanon Municipal, returning Mon, Feb 15, priced at $200 found 2 days ago
Sat, Nov 14 - Sat, Nov 21
PHL
Philadelphia Intl.
RUT
Rutland Southern Vermont Regional
$452 Roundtrip, found 1 day ago
$452
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Nov 14 from Philadelphia Intl. to Rutland Southern Vermont Regional, returning Sat, Nov 21, priced at $452 found 1 day ago
Thu, Sep 3 - Thu, Sep 10
PHL
Philadelphia Intl.
LEB
Lebanon Municipal
$453 Roundtrip, found 14 hours ago
$453
Roundtrip
found 14 hours ago
Select Delta flight, departing Thu, Sep 3 from Philadelphia Intl. to Lebanon Municipal, returning Thu, Sep 10, priced at $453 found 14 hours ago
Thu, Sep 10 - Sat, Sep 12
TTN
Mercer
RUT
Rutland Southern Vermont Regional
$486 Roundtrip, found 5 days ago
$486
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Sep 10 from Mercer to Rutland Southern Vermont Regional, returning Sat, Sep 12, priced at $486 found 5 days ago

Best Windsor County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Deerfield Valley Inn
2.0-star property

Deerfield Valley Inn

Oct 9 - Oct 13

4 night stay

Philadelphia (PHL) to Springfield (VSF)

American Airlines • Roundtrip • Coach
Price was $971, price is now $833 per person
$833
per person
found 1 day ago
Latchis Hotel
2.5-star property

Latchis Hotel

Oct 9 - Oct 13

4 night stay

Philadelphia (PHL) to Springfield (VSF)

American Airlines • Roundtrip • Coach
Price was $1,077, price is now $901 per person
$901
per person
found 1 day ago
The Landgrove
3.5-star property

The Landgrove

Oct 9 - Oct 13

4 night stay

Philadelphia (PHL) to Rutland (RUT)

American Airlines • Roundtrip • Coach
Price was $1,277, price is now $1,074 per person
$1,074
per person
found 1 day ago
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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 $486. 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.