Cheap Flight Deals to Windsor VT from CA $868

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How to find cheap flights to Windsor?

The cheapest prices found with in the last 7 days for return flights were CA $564 and CA $868 for one-way flights to Windsor for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
DCANorth ClarendonJanuary 17 to January 19CA $581
*Prices include taxes and fees

Your guide to flights to Windsor, VT

JetBlue Airways, American Airlines, Delta, Cape Air fly to Windsor, so use Travelocity to search, find, and compare some truly tempting deals from the 4 airlines—that way you can be sure you’ve found the best deal for you. A flight to Windsor VT currently costs between CA $564 and CA $868. Prices vary, but for the best fares, travel in December when prices are at their lowest.  

Top tips for finding cheap flights to Windsor  

The cheapest flight for a round trip to Windsor is currently CA $564. When you search for flights to Windsor, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Windsor for nearby days.  The cheapest month to travel to Windsor is February from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Windsor 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Windsor with Travelocity 

We have top deals on plane tickets even for last minute flights to Windsor, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Windsor for less. 

Find The Perfect Hotel For After Your Flight

Luxury Hotels in Windsor

Snapdragon Inn

Snapdragon Inn

3.5 out of 5
26 Main Street, Windsor, VT
Stay at this 3.5-star B&B in Windsor. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Old Constitution House and South Congregational ...
9.4/10 Exceptional! (17 reviews)
"The history of the house is provided. Beutiful house and grounds."

Reviewed on 4 Aug. 2019

Snapdragon 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.

Need a car after flight to Windsor?

Frequently asked questions

Which airlines fly to Windsor?
Getting ready to make some amazing new memories in Windsor? Cape Air is one of the top airline companies that service this destination.
What airport is best to fly into Windsor?
Before securing your flight to Windsor, keep in mind that it has two airports. Lebanon Municipal Airport (LEB) is 18 kilometers from the center of the city, while Rutland Southern Vermont Regional Airport is approximately 40 kilometers from the downtown area.
Where to stay in Windsor
Life is one epic journey, so why not get out there and really experience it in Windsor? You can start by selecting from the 57 sensational properties available there through Travelocity.If you’re looking for comfortable accommodations in Windsor, we suggest the Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel and the Windsor Mansion Inn. Secure a room and then start organizing all those amazing getaway experiences.
Places to visit in Windsor
0 Want more options? 0
How to get through airport security fast when traveling to Windsor
These clever tips and hints about airport security checks will save you lots of time and energy on your journey to Windsor:

  • Have your boarding pass and passport within easy reach. They’ll be the first things you’ll be told to produce by security staff.
  • Take off your belt and shoes before arriving at the security checkpoint. Items like these are not permitted to pass through the body scanner.
  • Electronic goods such as laptops, phones and cameras will need to be sent through the X-ray machine separately. Make sure they’re within easy reach.
  • Traveling with a new cologne? As long as it’s no greater than 3.4 ounces (100 milliliters) and it’s stored in a clear resealable plastic bag, you can keep it with you in your carry-on luggage.
  • Undo your shoelaces as you approach the body scanner. Depending on the type of shoes you’ve got on, security may ask you to remove them.
  • Pack any multi-tools or other dangerous items inside your checked luggage. Airport security won’t permit these aboard the aircraft.

Plane Tickets To Windsor

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Windsor. Browse through our inventory to explore a wide range of cheap flights to Windsor to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Windsor as you anxiously await to exit the plane and explore what Windsor has to offer. Considering all the amazing local food and culture in Windsor, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Windsor to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Windsor without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Windsor with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Windsor today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.