Cheap Flights to Windsor County from $79 (2026/2027)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Windsor County's top cities

A red convertible car parked in front of a brick house with black shutters and a white picket fence.

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, Jul 11 - Fri, Jul 17
BOS
Logan Intl.
LEB
Lebanon Municipal
$162 Roundtrip, found 6 days ago
$162
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sat, Jul 11 from Logan Intl. to Lebanon Municipal, returning Fri, Jul 17, priced at $162 found 6 days ago
Mon, Jul 13 - Sun, Jul 19
BOS
Logan Intl.
LEB
Lebanon Municipal
$168 Roundtrip, found 4 days ago
$168
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, Jul 13 from Logan Intl. to Lebanon Municipal, returning Sun, Jul 19, priced at $168 found 4 days ago
Sat, Jul 11 - Mon, Jul 13
BOS
Logan Intl.
LEB
Lebanon Municipal
$172 Roundtrip, found 2 days ago
$172
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, Jul 11 from Logan Intl. to Lebanon Municipal, returning Mon, Jul 13, priced at $172 found 2 days ago
Thu, Jul 23 - Mon, Jul 27
BOS
Logan Intl.
LEB
Lebanon Municipal
$173 Roundtrip, found 19 hours ago
$173
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Thu, Jul 23 from Logan Intl. to Lebanon Municipal, returning Mon, Jul 27, priced at $173 found 19 hours ago
Sat, Jul 25 - Sat, Aug 1
BOS
Logan Intl.
LEB
Lebanon Municipal
$173 Roundtrip, found 4 hours ago
$173
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Sat, Jul 25 from Logan Intl. to Lebanon Municipal, returning Sat, Aug 1, priced at $173 found 4 hours ago
Mon, Jul 13 - Sun, Jul 19
BOS
Logan Intl.
LEB
Lebanon Municipal
$175 Roundtrip, found 4 days ago
$175
Roundtrip
found 4 days ago
Select Cape Air flight, departing Mon, Jul 13 from Logan Intl. to Lebanon Municipal, returning Sun, Jul 19, priced at $175 found 4 days ago
Fri, Sep 25 - Sun, Sep 27
BOS
Logan Intl.
LEB
Lebanon Municipal
$175 Roundtrip, just found
$175
Roundtrip
just found
Select Cape Air flight, departing Fri, Sep 25 from Logan Intl. to Lebanon Municipal, returning Sun, Sep 27, priced at $175 just found
Fri, Oct 16 - Mon, Oct 19
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 7 hours ago
$180
Roundtrip
found 7 hours ago
Select Cape Air flight, departing Fri, Oct 16 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Oct 19, priced at $180 found 7 hours ago
Fri, Jul 31 - Fri, Jul 31
HPN
Westchester County
LEB
Lebanon Municipal
$220 Roundtrip, found 1 day ago
$220
Roundtrip
found 1 day ago
Select Cape Air flight, departing Fri, Jul 31 from Westchester County to Lebanon Municipal, returning Fri, Jul 31, priced at $220 found 1 day ago

Best Windsor County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Deerfield Valley Inn
2.0-star property

Deerfield Valley Inn

Oct 1 - Oct 5

4 night stay

Baltimore (BWI) to Springfield (VSF)

Southwest Airlines • Roundtrip • Coach
Price was $719, price is now $541 per person
$541
per person
found 7 hours ago
Vikings Villages Resort
2.0-star property

Vikings Villages Resort

Oct 1 - Oct 5

4 night stay

Baltimore (BWI) to Springfield (VSF)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $937, price is now $658 per person
$658
per person
found 7 hours ago
Harvest Barn Inn
3.0-star property

Harvest Barn Inn

Oct 1 - Oct 5

4 night stay

Baltimore (BWI) to Rutland (RUT)

Southwest Airlines • Roundtrip • Coach
Price was $701, price is now $546 per person
$546
per person
found 7 hours ago
Don't see what you're looking for?
See all available trips from Baltimore to Windsor County
View all trips

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! (1,239 reviews)
"The Inn is opposite Quechee Gorge so a great location. The room itself could do with updating but was still comfortable. It was easy to check-in and my request for a room away from vending machines and AC generators was honored but it was overlooking the road (US-4) so there was significant noise ..."

Reviewed on Jul 8, 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 Quechee Gorge Bridge and Middle Covered Bridge are located nearby.
9.4/10 Exceptional! (589 reviews)
"Had a short stay with my family to the Woodstock Inn and would love to return some day. Hospitality at its best in a beautiful town. The grounds and amenities were immaculate and authentic to the area. A memorable stay."

Reviewed on Jun 25, 2026

Opens in a new windowWoodstock Inn & Resort
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.
9.4/10 Exceptional! (1,006 reviews)
"convenient location with very comfortable accommodations"

Reviewed on Jul 7, 2026

Opens in a new windowOn The River Inn
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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 Quechee Gorge Bridge and Billings Park and Trail are located nearby.
8.8/10 Excellent! (961 reviews)
"Absolutely beautiful setting! The room was better than expected-- spacious, clean and gorgeously decorated. The location was also great-- everything was walkable. Highly recommend."

Reviewed on Jul 5, 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 $162 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 July. 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 $162. 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 $162 and $220. 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.