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.

Sat, Feb 13 - Sat, Feb 20
BOS
Logan Intl.
LEB
Lebanon Municipal
$135 Roundtrip, found 2 days ago
$135
Roundtrip
found 2 days ago
Select Cape Air flight, departing Sat, Feb 13 from Logan Intl. to Lebanon Municipal, returning Sat, Feb 20, priced at $135 found 2 days ago
Fri, Jan 1 - Thu, Jan 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$145 Roundtrip, found 3 days ago
$145
Roundtrip
found 3 days ago
Select Cape Air flight, departing Fri, Jan 1 from Logan Intl. to Lebanon Municipal, returning Thu, Jan 7, priced at $145 found 3 days ago
Thu, Nov 5 - Mon, Nov 9
BOS
Logan Intl.
LEB
Lebanon Municipal
$155 Roundtrip, found 4 hours ago
$155
Roundtrip
found 4 hours ago
Select Cape Air flight, departing Thu, Nov 5 from Logan Intl. to Lebanon Municipal, returning Mon, Nov 9, priced at $155 found 4 hours ago
Thu, Nov 5 - Sun, Nov 8
BOS
Logan Intl.
LEB
Lebanon Municipal
$158 Roundtrip, found 4 days ago
$158
Roundtrip
found 4 days ago
Select Cape Air flight, departing Thu, Nov 5 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 8, priced at $158 found 4 days ago
Thu, Nov 5 - Mon, Nov 9
BOS
Logan Intl.
LEB
Lebanon Municipal
$165 Roundtrip, found 4 hours ago
$165
Roundtrip
found 4 hours ago
Select Cape Air flight, departing Thu, Nov 5 from Logan Intl. to Lebanon Municipal, returning Mon, Nov 9, priced at $165 found 4 hours ago
Thu, Nov 5 - Sun, Nov 8
BOS
Logan Intl.
LEB
Lebanon Municipal
$168 Roundtrip, found 4 days ago
$168
Roundtrip
found 4 days ago
Select Cape Air flight, departing Thu, Nov 5 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 8, priced at $168 found 4 days ago
Thu, Nov 5 - Mon, Nov 9
BOS
Logan Intl.
LEB
Lebanon Municipal
$175 Roundtrip, found 4 hours ago
$175
Roundtrip
found 4 hours ago
Select Cape Air flight, departing Thu, Nov 5 from Logan Intl. to Lebanon Municipal, returning Mon, Nov 9, priced at $175 found 4 hours ago
Wed, Dec 23 - Sun, Dec 27
HPN
Westchester County
LEB
Lebanon Municipal
$180 Roundtrip, found 5 days ago
$180
Roundtrip
found 5 days ago
Select Cape Air flight, departing Wed, Dec 23 from Westchester County to Lebanon Municipal, returning Sun, Dec 27, priced at $180 found 5 days ago
Tue, Oct 27 - Thu, Oct 29
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$395 Roundtrip, found 2 days ago
$395
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Oct 27 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Thu, Oct 29, priced at $395 found 2 days ago

Best Windsor County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Landgrove
3.5-star property

The Landgrove

Nov 12 - Nov 15

3 night stay

Raleigh (RDU) to Rutland (RUT)

Breeze Airways • Roundtrip • Coach
Price was $621, price is now $518 per person
$518
per person
found 1 day ago
Mountain Green Resort
4.0-star property

Mountain Green Resort

Oct 10 - Oct 12

2 night stay

Denver (DEN) to Rutland (RUT)

United • Roundtrip • Coach
Price was $3,302, price is now $2,698 per person
$2,698
per person
found 1 day ago
The Weston
5.0-star property

The Weston

Nov 12 - Nov 15

3 night stay

Raleigh (RDU) to Springfield (VSF)

Breeze Airways • Roundtrip • Coach
Price was $1,051, price is now $886 per person
$886
per person
found 1 day 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! (1,380 reviews)
"Room was good size and bathroom area was adequate for two people. There was some audible road noise. Breakfast was ok with cold breakfast sandwiches that could be heated up in the microwave."

Reviewed on Oct 9, 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.
Opens in a new windowWoodstock Inn & Resort
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
111 Jackson Gore Road Ludlow VT
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Timber Ripper Mountain Coaster are located nearby.
8.6/10 Excellent! (918 reviews)
"The staff is amazing here at Jackson Gore Village. There were actually some issues with our stay and we reported to the front desk. The staff was really helpful and took care of the issue immediately. Katie, the manager, followed up the next day and further resolved the issue. The way they treat ..."

Reviewed on Oct 9, 2026

Opens in a new windowJackson Gore Village, A Vail Resorts Property
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The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast in our reviews. Popular attractions Union Arena Community Center and Five Elm Arches are located nearby.
Opens in a new windowThe Jackson
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 $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 February. 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 $395. 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.