Deals on vacations and trips to Windsor

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Windsor flight + hotel vacation packages

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Best Western Plus Waterfront Hotel
Caesars Windsor
Comfort Inn & Suites Ambassador Bridge

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Popular places to visit

Windsor Vacations

Windsor, Ontario, shares its booming industrial past with its sister city across the river, Detroit. Nowadays, this quiet Canadian city is known for nature more than machines. Windsor becomes more reminiscent of its roots as a French agricultural town daily, as tourists embark on Windsor vacations for a piece of economical serenity. Known for its proud multicultural population, Windsor's small-town feel but big city cosmopolitanism make for an ideal combination.

Major Attractions

Simply strolling through Windsor and stopping in all the cultural shops and restaurants is attraction enough. Start in downtown and head east to visit the North African and Middle Eastern neighborhoods, west to taste some Asian influences, and south to experience Windsor's Little Italy. Don't miss the Serbian Heritage Museum for more multicultural fun, and Willistead Manor for a taste of Windsor's sophisticated past. Head to the Dieppe Gardens by the river for a relaxing environment and extraordinary view of Detroit's skyline. And no vacation in Windsor is complete without visiting Odette Sculpture Park, heralded as an outdoor museum.

Recurring Events and Festivals

Reflective of its multicultural atmosphere, Windsor has a variety of festivals throughout the year. Patriotic people should search for Windsor vacation packages in July to experience the Windsor-Detroit International Freedom Festival, a joint celebration of Canada Day and American Independence day. Later in July is Bluesfest International, a fantastic event showcasing local music which appeals to music lovers everywhere. But the most famous festival of all is the Windsor Emancipation Celebration Festival in early August. In the past, more than a quarter million people flocked from all over to attend this event in Windsor, the largest of its kind. While the event is no longer quite so huge, it still has all the wonders and fervor of years past.

Windsor hotels will put you in the center of the action, close to all that this post-industrial Canadian gem has to offer. Search for Windsor rental cars on Travelocity and benefit from the Travelocity Price Guarantee. We'll match a lower price and refund the difference!

Frequently asked questions

How much are vacation packages to Windsor?
With Travelocity vacation packages, you could be living it up in Windsor for as little as $445. Activities, hotels and flights — we’re a one-stop shop for all of them. You can save some cash just for bundling together your bookings. And with all that taken care of before you set off, you won’t have a care in the world.
How long should my Windsor vacation be?
Most people lock in their hotel for 2 nights in Windsor. But that doesn’t necessarily mean you have to follow suit. How long you stick around depends on what sorts of things you want to do during your vacation. If you want to see every corner of this amazing location, stay another night or two (or even an extra week!).
Where can I get the best vacation package deals for Windsor?
Head straight to Travelocity. With access to 400 air carriers and an impressive 1,000,000 hotels around the world, finding the best Windsor package deal couldn’t be simpler.
Why should I book my Windsor vacation bundle with Travelocity?
You’ll not only enjoy big savings, but you’ll also have access to our 24/7 customer support, top-notch service and a Price Match Guarantee. Wander across the world, discover hidden gems and make unforgettable memories — we’ll take care of the little details.
Can I save on my Windsor car rental if I combine it with hotels and flights?
Bundling your car, flight and hotel into a Windsor vacation package is a great way to land the best deal. Plus, having your own car rental gives you the freedom to get to all those famous sights you’re itching to see. Located 110 mi from Windsor, Geneva State Park is one place that should be on your agenda. Put together a driving playlist and make a day trip of it.
Which airport is best for Windsor?
Detroit Metropolitan Wayne County Airport (DTW) is one of the best airports for Windsor. It’s located 17 mi west of the bustling downtown area. Other options available to you are Bishop Intl. Airport (FNT) (60 mi away from central Windsor) and Windsor Airport (YQG) (5 mi away from central Windsor).
What is there to do in Windsor?
You’ll notice a certain magic as you wander through the streets of Windsor. Detroit Windsor Tunnel and Caesars Casino are just two attractions that make this city such a sought-after destination, so put them at the top of your must-see list.
Where should I stay when visiting Windsor?
The Comfort Inn & Suites Ambassador Bridge is the top choice of many visitors. Book as soon as possible before it’s too late.

Photos of local treasures

Browse Windsor vacation photos for more inspiration

Windsor which includes a city
Walkerville showing autumn leaves and a city
Willistead Park Trail Trailhead featuring a park, heritage elements and a house
Wolfville showing a sunset
Point Pelee National Park which includes wetlands and a bridge