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 hour ago
$155
Roundtrip
found 1 hour ago
Select Cape Air flight, departing Sun, Nov 1 from Logan Intl. to Lebanon Municipal, returning Sat, Nov 7, priced at $155 found 1 hour ago
Sun, Nov 1 - Sat, Nov 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$165 Roundtrip, found 1 hour ago
$165
Roundtrip
found 1 hour ago
Select Cape Air flight, departing Sun, Nov 1 from Logan Intl. to Lebanon Municipal, returning Sat, Nov 7, priced at $165 found 1 hour ago
Tue, Oct 20 - Sat, Oct 24
BOS
Logan Intl.
LEB
Lebanon Municipal
$175 Roundtrip, found 2 days ago
$175
Roundtrip
found 2 days ago
Select Cape Air flight, departing Tue, Oct 20 from Logan Intl. to Lebanon Municipal, returning Sat, Oct 24, priced at $175 found 2 days ago
Thu, Sep 10 - Mon, Sep 14
BOS
Logan Intl.
LEB
Lebanon Municipal
$178 Roundtrip, found 1 hour ago
$178
Roundtrip
found 1 hour ago
Select Cape Air flight, departing Thu, Sep 10 from Logan Intl. to Lebanon Municipal, returning Mon, Sep 14, priced at $178 found 1 hour 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 4 days ago
$182
Roundtrip
found 4 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 4 days ago
Tue, Oct 20 - Sat, Oct 24
BOS
Logan Intl.
LEB
Lebanon Municipal
$185 Roundtrip, found 2 days ago
$185
Roundtrip
found 2 days ago
Select Cape Air flight, departing Tue, Oct 20 from Logan Intl. to Lebanon Municipal, returning Sat, Oct 24, priced at $185 found 2 days ago
Fri, Sep 4 - Sun, Sep 6
BOS
Logan Intl.
LEB
Lebanon Municipal
$188 Roundtrip, found 2 days ago
$188
Roundtrip
found 2 days ago
Select Cape Air flight, departing Fri, Sep 4 from Logan Intl. to Lebanon Municipal, returning Sun, Sep 6, priced at $188 found 2 days ago
Mon, Sep 14 - Tue, Sep 15
RIC
Richmond Intl.
LEB
Lebanon Municipal
$550 Roundtrip, found 5 days ago
$550
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Sep 14 from Richmond Intl. to Lebanon Municipal, returning Tue, Sep 15, priced at $550 found 5 days ago
Thu, Sep 17 - Wed, Sep 23
RIC
Richmond Intl.
LEB
Lebanon Municipal
$557 Roundtrip, found 4 days ago
$557
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Sep 17 from Richmond Intl. to Lebanon Municipal, returning Wed, Sep 23, priced at $557 found 4 days ago
Thu, Sep 17 - Wed, Sep 23
RIC
Richmond Intl.
LEB
Lebanon Municipal
$562 Roundtrip, found 4 days ago
$562
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Sep 17 from Richmond Intl. to Lebanon Municipal, returning Wed, Sep 23, priced at $562 found 4 days ago

Best Windsor County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast
4.0-star property

Sinclair Inn Bed and Breakfast

Nov 8 - Nov 14

6 night stay

Portland (PDX) to Springfield (VSF)

United • Non-stop roundtrip • Coach
Price was $1,126, price is now $962 per person
$962
per person
found 21 hours ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0-star property

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Oct 1 - Oct 4

3 night stay

Detroit (DTW) to Rutland (RUT)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,221, price is now $1,046 per person
$1,046
per person
found 2 hours ago
The Landgrove
3.5-star property

The Landgrove

Oct 1 - Oct 4

3 night stay

Detroit (DTW) to Rutland (RUT)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,153, price is now $1,041 per person
$1,041
per person
found 2 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.
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
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! (1,008 reviews)
"Very nice staff, but the property have large space to improve such as the windows, we have very noisy night,"

Reviewed on Aug 30, 2026

Opens in a new windowHotel Coolidge
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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
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 20 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 $562. 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.