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.

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
Tue, Oct 20 - Sat, Oct 24
BOS
Logan Intl.
LEB
Lebanon Municipal
$175 Roundtrip, found 1 day ago
$175
Roundtrip
found 1 day ago
Select Cape Air flight, departing Tue, Oct 20 from Logan Intl. to Lebanon Municipal, returning Sat, Oct 24, priced at $175 found 1 day ago
Sat, Oct 17 - Sat, Oct 17
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$177 Roundtrip, found 6 days ago
$177
Roundtrip
found 6 days ago
Select Cape Air flight, departing Sat, Oct 17 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Oct 17, priced at $177 found 6 days ago
Thu, Sep 10 - Mon, Sep 14
BOS
Logan Intl.
LEB
Lebanon Municipal
$178 Roundtrip, found 4 hours ago
$178
Roundtrip
found 4 hours ago
Select Cape Air flight, departing Thu, Sep 10 from Logan Intl. to Lebanon Municipal, returning Mon, Sep 14, priced at $178 found 4 hours ago
Sun, Dec 6 - Sun, Dec 13
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 2 days ago
$180
Roundtrip
found 2 days ago
Select Cape Air flight, departing Sun, Dec 6 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Dec 13, priced at $180 found 2 days ago
Sat, Sep 5 - Sat, Sep 12
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$182 Roundtrip, found 3 days ago
$182
Roundtrip
found 3 days ago
Select Cape Air flight, departing Sat, Sep 5 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 12, priced at $182 found 3 days ago
Tue, Oct 20 - Sat, Oct 24
BOS
Logan Intl.
LEB
Lebanon Municipal
$185 Roundtrip, found 1 day ago
$185
Roundtrip
found 1 day ago
Select Cape Air flight, departing Tue, Oct 20 from Logan Intl. to Lebanon Municipal, returning Sat, Oct 24, priced at $185 found 1 day ago
Thu, May 13 - Sun, May 16
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$590 Roundtrip, found 6 days ago
$590
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Thu, May 13 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Sun, May 16, priced at $590 found 6 days ago

Best Windsor County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Latchis Hotel
2.5-star property

Latchis Hotel

Sep 25 - Sep 28

3 night stay

Newark Liberty Intl. Airport (EWR) to Springfield (VSF)

United • Non-stop roundtrip • Coach
Price was $923, price is now $754 per person
$754
per person
found 5 hours ago
The Shire Woodstock
3.0-star property

The Shire Woodstock

Nov 5 - Nov 8

3 night stay

Newark Liberty Intl. Airport (EWR) to Springfield (VSF)

United • Non-stop • Coach

Springfield (VSF) to Newark Liberty Intl. Airport (EWR)

Cape Air • Non-stop • Coach
Price was $1,322, price is now $1,048 per person
$1,048
per person
found 5 hours ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0-star property

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Sep 25 - Sep 28

3 night stay

Newark Liberty Intl. Airport (EWR) to Rutland (RUT)

United • Non-stop roundtrip • Coach
Price was $1,052, price is now $863 per person
$863
per person
found 5 hours 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! (1,308 reviews)
"First night of three, great room, very comfortable. Went to get coffee, came back, key worked. Went for awesome breakfast provided, key didn't work. Even desk master card didn't work. They were going to change the battery so we went exploring. Got back, still not working so were moved to another ..."

Reviewed on Aug 29, 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.
9.4/10 Exceptional! (599 reviews)
"Amazing! Will visit again."

Reviewed on Aug 7, 2026

Opens in a new windowWoodstock Inn & Resort
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.
9.2/10 Wonderful! (1,001 reviews)
"This was one of the nicest hotels I have ever stayed in! We had a river view room with rocking chairs on the balcony, s’mores kits were offered every night (pick up by the front desk) and 2 fire pits to choose from. Game room was cute (although the air hockey table’s fan wasn’t strong on one side), ..."

Reviewed on Aug 29, 2026

Opens in a new windowOn The River Inn
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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! (868 reviews)
"The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus."

Reviewed on Aug 22, 2026

Opens in a new windowHoliday Inn Club Vacations Mount Ascutney Resort by IHG
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 $590. 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.