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.

Sat, Feb 13 - Sat, Feb 20
BOS
Logan Intl.
LEB
Lebanon Municipal
$135 Roundtrip, found 3 days ago
$135
Roundtrip
found 3 days ago
Select Cape Air flight, departing Sat, Feb 13 from Logan Intl. to Lebanon Municipal, returning Sat, Feb 20, priced at $135 found 3 days ago
Fri, Jan 1 - Thu, Jan 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$145 Roundtrip, found 3 days ago
$145
Roundtrip
found 3 days ago
Select Cape Air flight, departing Fri, Jan 1 from Logan Intl. to Lebanon Municipal, returning Thu, Jan 7, priced at $145 found 3 days ago
Mon, Dec 14 - Mon, Dec 14
BOS
Logan Intl.
LEB
Lebanon Municipal
$150 Roundtrip, found 2 hours ago
$150
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Mon, Dec 14 from Logan Intl. to Lebanon Municipal, returning Mon, Dec 14, priced at $150 found 2 hours ago
Sun, Nov 1 - Wed, Nov 4
BOS
Logan Intl.
LEB
Lebanon Municipal
$155 Roundtrip, just found
$155
Roundtrip
just found
Select Cape Air flight, departing Sun, Nov 1 from Logan Intl. to Lebanon Municipal, returning Wed, Nov 4, priced at $155 just found
Thu, Nov 5 - Sun, Nov 8
BOS
Logan Intl.
LEB
Lebanon Municipal
$158 Roundtrip, found 4 days ago
$158
Roundtrip
found 4 days ago
Select Cape Air flight, departing Thu, Nov 5 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 8, priced at $158 found 4 days ago
Mon, Dec 14 - Mon, Dec 14
BOS
Logan Intl.
LEB
Lebanon Municipal
$160 Roundtrip, found 2 hours ago
$160
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Mon, Dec 14 from Logan Intl. to Lebanon Municipal, returning Mon, Dec 14, priced at $160 found 2 hours ago
Fri, Jan 1 - Thu, Jan 7
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$160 Roundtrip, found 9 hours ago
$160
Roundtrip
found 9 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 9 hours ago
Sun, Nov 1 - Wed, Nov 4
BOS
Logan Intl.
LEB
Lebanon Municipal
$165 Roundtrip, just found
$165
Roundtrip
just found
Select Cape Air flight, departing Sun, Nov 1 from Logan Intl. to Lebanon Municipal, returning Wed, Nov 4, priced at $165 just found
Thu, Dec 10 - Sun, Dec 13
SRQ
Sarasota-Bradenton Intl.
RUT
Rutland Southern Vermont Regional
$496 Roundtrip, found 1 day ago
$496
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Dec 10 from Sarasota-Bradenton Intl. to Rutland Southern Vermont Regional, returning Sun, Dec 13, priced at $496 found 1 day ago

Best Windsor County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Vikings Villages Resort
2.0-star property

Vikings Villages Resort

Dec 18 - Dec 20

2 night stay

Houston (IAH) to Springfield (VSF)

Delta • Non-stop • Coach

Springfield (VSF) to Houston (IAH)

American Airlines • Non-stop • Coach
Price was $761, price is now $652 per person
$652
per person
found 11 hours ago
My Place Hotel-Randolph VT
2.0-star property

My Place Hotel-Randolph VT

Dec 20 - Dec 27

7 night stay

Houston (HOU) to Rutland (RUT)

American Airlines • Non-stop roundtrip • Coach
Price was $1,280, price is now $1,100 per person
$1,100
per person
found 1 day ago
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0-star property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Dec 14 - Dec 17

3 night stay

San Antonio (SAT) to Rutland (RUT)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $977, price is now $866 per person
$866
per person
found 14 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! (1,382 reviews)
"Y"

Reviewed on Oct 10, 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.
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.
Opens in a new windowJackson Gore Village, A Vail Resorts Property
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The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast in our reviews. Popular attractions Union Arena Community Center and Five Elm Arches are located nearby.
Opens in a new windowThe Jackson
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 February. 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 $496. 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.