Cheap Flights to Windsor County from $77 (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.

Tue, Mar 23 - Tue, Mar 30
BOS
Logan Intl.
LEB
Lebanon Municipal
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select Cape Air flight, departing Tue, Mar 23 from Logan Intl. to Lebanon Municipal, returning Tue, Mar 30, priced at $155 found 1 day ago
Wed, Nov 25 - Sun, Nov 29
BOS
Logan Intl.
LEB
Lebanon Municipal
$165 Roundtrip, found 1 day ago
$165
Roundtrip
found 1 day ago
Select Cape Air flight, departing Wed, Nov 25 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 29, priced at $165 found 1 day ago
Mon, Oct 19 - Mon, Oct 19
BOS
Logan Intl.
LEB
Lebanon Municipal
$170 Roundtrip, found 5 days ago
$170
Roundtrip
found 5 days ago
Select Cape Air flight, departing Mon, Oct 19 from Logan Intl. to Lebanon Municipal, returning Mon, Oct 19, priced at $170 found 5 days ago
Wed, Nov 25 - Sun, Nov 29
BOS
Logan Intl.
LEB
Lebanon Municipal
$175 Roundtrip, found 1 day ago
$175
Roundtrip
found 1 day ago
Select Cape Air flight, departing Wed, Nov 25 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 29, priced at $175 found 1 day ago
Sun, Aug 30 - Sun, Sep 6
BOS
Logan Intl.
LEB
Lebanon Municipal
$178 Roundtrip, found 16 hours ago
$178
Roundtrip
found 16 hours ago
Select Cape Air flight, departing Sun, Aug 30 from Logan Intl. to Lebanon Municipal, returning Sun, Sep 6, priced at $178 found 16 hours ago
Thu, Oct 22 - Thu, Oct 22
BOS
Logan Intl.
LEB
Lebanon Municipal
$180 Roundtrip, found 2 days ago
$180
Roundtrip
found 2 days ago
Select Cape Air flight, departing Thu, Oct 22 from Logan Intl. to Lebanon Municipal, returning Thu, Oct 22, priced at $180 found 2 days ago
Fri, Oct 16 - Sun, Oct 18
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 4 days ago
$180
Roundtrip
found 4 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 4 days ago
Fri, Oct 9 - Mon, Oct 12
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$183 Roundtrip, found 16 hours ago
$183
Roundtrip
found 16 hours ago
Select Cape Air flight, departing Fri, Oct 9 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Oct 12, priced at $183 found 16 hours ago
Fri, Feb 12 - Mon, Feb 15
HPN
Westchester County
LEB
Lebanon Municipal
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Cape Air flight, departing Fri, Feb 12 from Westchester County to Lebanon Municipal, returning Mon, Feb 15, priced at $200 found 1 day ago

Best Windsor County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Mount Snow Lodging by Vail Resorts
3.0-star property

Mount Snow Lodging by Vail Resorts

Oct 3 - Oct 10

7 night stay

New Orleans (MSY) to Springfield (VSF)

Breeze Airways • Non-stop • Coach

Springfield (VSF) to New Orleans (MSY)

American Airlines • Non-stop • Coach
Price was $1,303, price is now $1,022 per person
$1,022
per person
found 20 hours ago
The Landgrove
3.5-star property

The Landgrove

Oct 3 - Oct 10

7 night stay

New Orleans (MSY) to Rutland (RUT)

Breeze Airways • Non-stop • Coach

Rutland (RUT) to New Orleans (MSY)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,760, price is now $1,273 per person
$1,273
per person
found 20 hours ago
1846 Inn and Tavern
3.0-star property

1846 Inn and Tavern

Oct 3 - Oct 10

7 night stay

New Orleans (MSY) to Springfield (VSF)

Breeze Airways • Non-stop • Coach

Springfield (VSF) to New Orleans (MSY)

American Airlines • Non-stop • Coach
Price was $1,371, price is now $1,092 per person
$1,092
per person
found 20 hours ago
Don't see what you're looking for?
See all available trips from New Orleans to Windsor County
View all trips

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! (1,289 reviews)
"From check in to check out the stay was great. The room was impeccably clean. The staff was friendly. The property was well-‘maintained. The pool was open and clean. Morning breakfast was good. The location is in walking distance to the gorge and restaurants. I’d definitely be back for another ..."

Reviewed on Aug 19, 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! (865 reviews)
"Laundry room in the building, get beds."

Reviewed on Aug 16, 2026

Opens in a new windowHoliday Inn Club Vacations Mount Ascutney Resort by IHG
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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.
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 March. 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 $200. 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.