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.

Fri, Jan 1 - Thu, Jan 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$135 Roundtrip, found 2 days ago
$135
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Jan 1 from Logan Intl. to Lebanon Municipal, returning Thu, Jan 7, priced at $135 found 2 days ago
Fri, Jan 1 - Thu, Jan 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$145 Roundtrip, found 2 days ago
$145
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Jan 1 from Logan Intl. to Lebanon Municipal, returning Thu, Jan 7, priced at $145 found 2 days ago
Mon, Dec 14 - Mon, Dec 14
BOS
Logan Intl.
LEB
Lebanon Municipal
$150 Roundtrip, found 4 days ago
$150
Roundtrip
found 4 days ago
Select Cape Air flight, departing Mon, Dec 14 from Logan Intl. to Lebanon Municipal, returning Mon, Dec 14, priced at $150 found 4 days ago
Sun, Oct 18 - Sun, Oct 25
BOS
Logan Intl.
LEB
Lebanon Municipal
$155 Roundtrip, found 3 hours ago
$155
Roundtrip
found 3 hours ago
Select Cape Air flight, departing Sun, Oct 18 from Logan Intl. to Lebanon Municipal, returning Sun, Oct 25, priced at $155 found 3 hours ago
Mon, Dec 14 - Mon, Dec 14
BOS
Logan Intl.
LEB
Lebanon Municipal
$160 Roundtrip, found 4 days ago
$160
Roundtrip
found 4 days ago
Select Cape Air flight, departing Mon, Dec 14 from Logan Intl. to Lebanon Municipal, returning Mon, Dec 14, priced at $160 found 4 days ago
Fri, Jan 1 - Thu, Jan 7
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$160 Roundtrip, found 21 hours ago
$160
Roundtrip
found 21 hours ago
Select Cape Air flight, departing Fri, Jan 1 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Jan 7, priced at $160 found 21 hours ago
Sun, Oct 18 - Sun, Oct 25
BOS
Logan Intl.
LEB
Lebanon Municipal
$165 Roundtrip, found 3 hours ago
$165
Roundtrip
found 3 hours ago
Select Cape Air flight, departing Sun, Oct 18 from Logan Intl. to Lebanon Municipal, returning Sun, Oct 25, priced at $165 found 3 hours ago
Sat, Jan 30 - Wed, Feb 3
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select Cape Air flight, departing Sat, Jan 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Feb 3, priced at $170 found 1 day ago
Wed, Dec 23 - Wed, Dec 30
HPN
Westchester County
LEB
Lebanon Municipal
$180 Roundtrip, found 4 days ago
$180
Roundtrip
found 4 days ago
Select Cape Air flight, departing Wed, Dec 23 from Westchester County to Lebanon Municipal, returning Wed, Dec 30, priced at $180 found 4 days ago

Best Windsor County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0-star property

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Nov 11 - Nov 13

2 night stay

Washington (DCA) to Rutland (RUT)

JetBlue Airways • Non-stop • Coach

Rutland (RUT) to Washington (DCA)

Cape Air • Non-stop • Coach
Price was $624, price is now $553 per person
$553
per person
found 1 day ago
Vikings Villages Resort
2.0-star property

Vikings Villages Resort

Nov 11 - Nov 13

2 night stay

Washington (DCA) to Springfield (VSF)

JetBlue Airways • Non-stop • Coach

Springfield (VSF) to Washington (DCA)

Cape Air • Non-stop • Coach
Price was $784, price is now $691 per person
$691
per person
found 1 day ago
Grand Summit Resort, A Vail Resorts Property
3.0-star property

Grand Summit Resort, A Vail Resorts Property

Nov 11 - Nov 13

2 night stay

Washington (DCA) to Springfield (VSF)

JetBlue Airways • Non-stop • Coach

Springfield (VSF) to Washington (DCA)

Cape Air • Non-stop • Coach
Price was $649, price is now $578 per person
$578
per person
found 1 day ago
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Travelers ❤️ These Windsor County 🏨

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
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! (1,397 reviews)
"Staff friendly. Clean room. Maybe more breakfast options."

Reviewed on Oct 15, 2026

Opens in a new windowAlign Inn Vermont
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! (937 reviews)
"After check in, we went to our room (516). When we walked in, there were people already there and they had slept in our beds! We were initially quite upset and I immediately went to the front desk and complained. To the benefit of management and the staff, they apologized many times for the misstep. ..."

Reviewed on Oct 16, 2026

Opens in a new windowJackson Gore Village, A Vail Resorts Property
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Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
8.8/10 Excellent! (1,000 reviews)
"My sister and I needed a very last minute place to stay after our VRBO rental was not what we thought. The ladies at the front desk were really nice and very help. The beds and pillows were very comfortable and the room was very clean. The only issue is the area, it’s a bit of a drive if you want ..."

Reviewed on Oct 13, 2026

Opens in a new windowPointe at Castle Hill Resort
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 January. 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 $180. 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.