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.

Sun, Nov 1 - Sat, Nov 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select Cape Air flight, departing Sun, Nov 1 from Logan Intl. to Lebanon Municipal, returning Sat, Nov 7, priced at $155 found 1 day ago
Sun, Nov 1 - Sat, Nov 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$165 Roundtrip, found 1 day ago
$165
Roundtrip
found 1 day ago
Select Cape Air flight, departing Sun, Nov 1 from Logan Intl. to Lebanon Municipal, returning Sat, Nov 7, priced at $165 found 1 day ago
Mon, Oct 19 - Mon, Oct 19
BOS
Logan Intl.
LEB
Lebanon Municipal
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select Cape Air flight, departing Mon, Oct 19 from Logan Intl. to Lebanon Municipal, returning Mon, Oct 19, priced at $170 found 1 day ago
Mon, Oct 19 - Mon, Oct 19
BOS
Logan Intl.
LEB
Lebanon Municipal
$175 Roundtrip, found 1 day ago
$175
Roundtrip
found 1 day ago
Select Cape Air flight, departing Mon, Oct 19 from Logan Intl. to Lebanon Municipal, returning Mon, Oct 19, priced at $175 found 1 day ago
Mon, Aug 17 - Sat, Aug 22
BOS
Logan Intl.
LEB
Lebanon Municipal
$178 Roundtrip, found 23 hours ago
$178
Roundtrip
found 23 hours ago
Select Cape Air flight, departing Mon, Aug 17 from Logan Intl. to Lebanon Municipal, returning Sat, Aug 22, priced at $178 found 23 hours ago
Mon, Oct 19 - Mon, Oct 19
BOS
Logan Intl.
LEB
Lebanon Municipal
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Select Cape Air flight, departing Mon, Oct 19 from Logan Intl. to Lebanon Municipal, returning Mon, Oct 19, priced at $180 found 1 day ago
Fri, Oct 16 - Sun, Oct 18
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day 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 1 day ago
Mon, Aug 31 - Fri, Sep 4
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$183 Roundtrip, found 15 hours ago
$183
Roundtrip
found 15 hours ago
Select Cape Air flight, departing Mon, Aug 31 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Sep 4, priced at $183 found 15 hours ago
Sat, Sep 26 - Fri, Oct 9
JFK
John F. Kennedy Intl.
LEB
Lebanon Municipal
$438 Roundtrip, found 1 day ago
$438
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Sep 26 from John F. Kennedy Intl. to Lebanon Municipal, returning Fri, Oct 9, priced at $438 found 1 day 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

Aug 30 - Sep 1

2 night stay

Sacramento (SMF) to Springfield (VSF)

United • Non-stop roundtrip • Coach
Price was $720, price is now $672 per person
$672
per person
found 10 hours ago
Mountain Green Resort
4.0-star property

Mountain Green Resort

Sep 10 - Sep 12

2 night stay

Trenton (TTN) to Rutland (RUT)

American Airlines • Coach

Rutland (RUT) to Trenton (TTN)

Cape Air • Coach
Price was $1,760, price is now $1,457 per person
$1,457
per person
found 20 hours ago
Lake Bomoseen Lodge
3.5-star property

Lake Bomoseen Lodge

Sep 22 - Sep 25

3 night stay

Little Rock (LIT) to Rutland (RUT)

American Airlines • Coach

Rutland (RUT) to Little Rock (LIT)

Cape Air • Coach
Price was $1,069, price is now $981 per person
$981
per person
found 7 hours ago
Don't see what you're looking for?
See all available trips from Sacramento 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! (1,288 reviews)
"Staff were not the least bit empathetic about try to cancel/refund a booking after a death of immediate family. Ignored messages. I do not recommend this place."

Reviewed on Aug 15, 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! (864 reviews)
"Lovely resort in a lovely place. Pool was closed for renovations, but restaurant nd bar was great with great food and drinks."

Reviewed on Aug 15, 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 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 $438. 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.