Cheap Flights to Windsor County from $90 (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, Sep 11 - Mon, Sep 14
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 Fri, Sep 11 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Sep 14, priced at $180 found 2 days ago
Thu, Jul 16 - Sun, Jul 19
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$184 Roundtrip, found 10 hours ago
$184
Roundtrip
found 10 hours ago
Select Cape Air flight, departing Thu, Jul 16 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Jul 19, priced at $184 found 10 hours ago
Mon, Jun 15 - Wed, Jun 17
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$186 Roundtrip, found 6 hours ago
$186
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Mon, Jun 15 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Jun 17, priced at $186 found 6 hours ago
Fri, Sep 11 - Mon, Sep 14
BOS
Logan Intl.
LEB
Lebanon Municipal
$190 Roundtrip, found 2 days ago
$190
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, Sep 11 from Logan Intl. to Lebanon Municipal, returning Mon, Sep 14, priced at $190 found 2 days ago
Mon, Jun 15 - Wed, Jun 17
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$190 Roundtrip, found 6 hours ago
$190
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Mon, Jun 15 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Jun 17, priced at $190 found 6 hours ago
Fri, Jul 17 - Sun, Jul 19
BOS
Logan Intl.
LEB
Lebanon Municipal
$194 Roundtrip, found 8 hours ago
$194
Roundtrip
found 8 hours ago
Select JetBlue Airways flight, departing Fri, Jul 17 from Logan Intl. to Lebanon Municipal, returning Sun, Jul 19, priced at $194 found 8 hours ago
Mon, Jun 15 - Wed, Jun 17
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$196 Roundtrip, found 6 hours ago
$196
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Mon, Jun 15 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Jun 17, priced at $196 found 6 hours ago
Thu, Aug 27 - Wed, Sep 2
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$383 Roundtrip, found 2 days ago
$383
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Aug 27 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Wed, Sep 2, priced at $383 found 2 days ago

Best Windsor County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Lake Bomoseen Lodge
3.5-star property

Lake Bomoseen Lodge

Jun 10 - Jun 12

2 night stay

Dallas (DFW) to Rutland (RUT)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $746, price is now $692 per person
$692
per person
found 3 hours ago
My Place Hotel-Randolph VT
2.0-star property

My Place Hotel-Randolph VT

Aug 2 - Aug 8

6 night stay

Cincinnati (CVG) to Lebanon (LEB)

American Airlines • Non-stop roundtrip • Coach
Price was $878, price is now $711 per person
$711
per person
found 1 day ago
Vikings Villages Resort
2.0-star property

Vikings Villages Resort

Jun 10 - Jun 12

2 night stay

Dallas (DFW) to Springfield (VSF)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $793, price is now $709 per person
$709
per person
found 3 hours ago
Don't see what you're looking for?
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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! (1,200 reviews)
"There were some issues with the layout of the room, namely that the bathroom and the kitchen share the same space! There was a main room with beds, tv and chairs (no problems in this room), and then a dividing barn door. On the other side of the barn door was a sink. To the right of the sink was ..."

Reviewed on May 27, 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! (580 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."

Reviewed on May 22, 2026

Opens in a new windowWoodstock Inn & Resort
Hotel Coolidge

Hotel Coolidge

3 out of 5
39 South Main Street White River Junction VT
Book a stay at this business-friendly hotel in White River Junction. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Briggs Opera House and Barrette Center for the Arts are located nearby.
8.2/10 Very Good! (1,001 reviews)
"Breakfast was amazing and the room was very comfortable."

Reviewed on May 26, 2026

Opens in a new windowHotel Coolidge
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The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
8.8/10 Excellent! (931 reviews)
"Yes"

Reviewed on May 18, 2026

Opens in a new windowThe Shire Woodstock
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 $180 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 15 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 September. 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 $180. 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 $180 and $383. 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.