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 6 hours ago
$135
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Fri, Jan 1 from Logan Intl. to Lebanon Municipal, returning Thu, Jan 7, priced at $135 found 6 hours ago
Sun, Dec 27 - Fri, Jan 1
BOS
Logan Intl.
LEB
Lebanon Municipal
$145 Roundtrip, found 4 hours ago
$145
Roundtrip
found 4 hours ago
Select Cape Air flight, departing Sun, Dec 27 from Logan Intl. to Lebanon Municipal, returning Fri, Jan 1, priced at $145 found 4 hours ago
Mon, Dec 14 - Mon, Dec 14
BOS
Logan Intl.
LEB
Lebanon Municipal
$150 Roundtrip, found 2 days ago
$150
Roundtrip
found 2 days ago
Select Cape Air flight, departing Mon, Dec 14 from Logan Intl. to Lebanon Municipal, returning Mon, Dec 14, priced at $150 found 2 days ago
Sun, Nov 8 - Sun, Nov 15
BOS
Logan Intl.
LEB
Lebanon Municipal
$155 Roundtrip, found 5 hours ago
$155
Roundtrip
found 5 hours ago
Select Cape Air flight, departing Sun, Nov 8 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 15, priced at $155 found 5 hours ago
Thu, Nov 5 - Sun, Nov 8
BOS
Logan Intl.
LEB
Lebanon Municipal
$158 Roundtrip, found 6 days ago
$158
Roundtrip
found 6 days ago
Select Cape Air flight, departing Thu, Nov 5 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 8, priced at $158 found 6 days ago
Mon, Dec 14 - Mon, Dec 14
BOS
Logan Intl.
LEB
Lebanon Municipal
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select Cape Air flight, departing Mon, Dec 14 from Logan Intl. to Lebanon Municipal, returning Mon, Dec 14, priced at $160 found 2 days ago
Fri, Jan 1 - Thu, Jan 7
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days 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 2 days ago
Sun, Nov 8 - Sun, Nov 15
BOS
Logan Intl.
LEB
Lebanon Municipal
$165 Roundtrip, found 5 hours ago
$165
Roundtrip
found 5 hours ago
Select Cape Air flight, departing Sun, Nov 8 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 15, priced at $165 found 5 hours ago
Thu, Jan 28 - Mon, Feb 1
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$290 Roundtrip, found 1 day ago
$290
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Jan 28 from Ronald Reagan Washington National to Lebanon Municipal, returning Mon, Feb 1, priced at $290 found 1 day 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

Dec 24 - Dec 31

7 night stay

Atlanta (ATL) to Springfield (VSF)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $1,003, price is now $784 per person
$784
per person
found 2 hours ago
Vikings Villages Resort
2.0-star property

Vikings Villages Resort

Dec 24 - Dec 31

7 night stay

Atlanta (ATL) to Springfield (VSF)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,529, price is now $1,097 per person
$1,097
per person
found 2 hours ago
Emrose Luxury Cabins
2.0-star property

Emrose Luxury Cabins

Oct 14 - Oct 21

7 night stay

Raleigh (RDU) to Rutland (RUT)

Southwest Airlines • Non-stop • Coach

Rutland (RUT) to Raleigh (RDU)

JetBlue Airways • Non-stop • Coach
Price was $1,451, price is now $1,143 per person
$1,143
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! (1,387 reviews)
"Great location and beautiful property and area. Breakfast was also great easy and quick. Only issue is not with hotel but that area needs more restaurants especially ones open after 6pm."

Reviewed on Oct 11, 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! (617 reviews)
"Room was spacious and very clean upon arrival. Staff was also very attentive and took care all our needs."

Reviewed on Oct 11, 2026

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! (925 reviews)
"Bed was a very uncomfortable Murphy bed which was not disclosed when booking. Property and room did not feel clean. Property amenities were nice and in a convenient location."

Reviewed on Oct 12, 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! (1,004 reviews)
"Room was adequate. Bedding was uncomfortable. We would not revisit this property. We would not recommend to others."

Reviewed on Oct 11, 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 $290. 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.