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Windsor Vacation Packages

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Top Hotels in Windsor

Best Western Plus Waterfront Hotel
Best Western Plus Waterfront Hotel
2.5 out of 5
277 Riverside Drive West, Windsor, ON
Free cancellationReserve now, pay when you stay
The price is CA $113 per night from Apr 23 to Apr 24
4.3/5Excellent! (2,085 reviews)
"Excellent location. Walking distance to beautiful gardens along the river. Only one microwave available in the lobby to warm up your self serve breakfast - not enough. There was no wipes available to clean the microwave for the use of the next passenger."

Reviewed on Apr. 7, 2021

Best Western Plus Waterfront Hotel
Hampton Inn & Suites by Hilton Windsor
Hampton Inn & Suites by Hilton Windsor
2.5 out of 5
1840 Huron Church Road, Windsor, ON
Free cancellationReserve now, pay when you stay
The price is CA $108 per night from Apr 25 to Apr 26
4.1/5Very Good! (848 reviews)
"It was located in the convenient place for my short business trip to Windsor."

Reviewed on Mar. 19, 2021

Hampton Inn & Suites by Hilton Windsor
Stonecroft Inn
Stonecroft Inn
3 out of 5
3032 Dougall Ave, Windsor, ON
Free cancellationReserve now, pay when you stay
The price is CA $105 per night from Apr 19 to Apr 20
4.6/5Exceptional! (113 reviews)
"The room is clean. Staffs are friendly."

Reviewed on Apr. 4, 2021

Stonecroft Inn
See all 124 properties in Windsor
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.

Top things to do in Windsor

Image for City Scavenger Hunts by Operation City Quest of Ohio

City Scavenger Hunts by Operation City Quest of Ohio

CA $13
Per adult
City Scavenger Hunts by Operation City Quest of Ohio
Image for Crazy Dash Walking Adventure of Michigan

Crazy Dash Walking Adventure of Michigan

CA $13
Per adult
Crazy Dash Walking Adventure of Michigan
Image for 3Quest Challenge Scavenger hunts of Michigan

3Quest Challenge Scavenger hunts of Michigan

CA $13
Per adult
3Quest Challenge Scavenger hunts of Michigan
See all activities in Windsor

What are the advantages of a road trip to Windsor?

Taking a Windsor road trip is the best way to travel while hitting all the stops along the way. There’s never been a better time to put all your road trip ideas to good use. Expedia offers incredible deals on hotels in Windsor, and you can save big when you opt for one of our packages in Windsor. Our packages combine your hotel and car rental into one low price, saving you more on both. 

How to plan a road trip to Windsor?

Planning a road trip is easy when you make all your itinerary bookings in one place—Expedia. You might take a camping road trip where all you need is a car and some gear. Car rentals are available in the pick-up and drop-off locations of your choosing. You might take a highway getaway to that city you’ve been dreaming of, bundling your hotel and car bookings for deep road trip discounts. 

What to do on a road trip to Windsor?

To make the most of any road trip adventure, you’ll want to have a road trip itinerary. That way, you won’t miss any of the road trip activities on your list. You can search for things to do in Windsor and other destinations before adding it to your plan.  

How to rent a car for a road trip?

Renting a car for a road trip is often the best way to travel. Don’t put miles or strain on your own vehicle and instead put your mind at ease when you opt for a safe car rental. Expedia offers wow-worthy deals on car rentals so you can choose the perfect car for your journey and preferences. Get the whole gang to pile in and hit the road for a great price. Vacation rentals in Windsor are waiting for you to arrive. Expedia will help you get there for less.

Frequently asked questions

How much does a Windsor vacation package cost?
From as low as , you can build your own Windsor vacation package. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
If I'm not able to travel, can I cancel my Windsor vacation package?
You can cancel or amend your booking, but whether or not you’ll incur a charge will depend on what and when you booked. If you’ve locked in a Windsor vacation package in the last 24 hours, it may be possible to cancel and rebook for free. For later changes, your airline, hotel or car rental company may impose additional costs. Browse our Customer Service Portal for further information.
How do I get a cheap travel package to Windsor?
Bundle your flights and hotels with Expedia and save an impressive C$590. With over 400 partner airlines and 321,000 hotel options globally, your Windsor vacation package can be customized exactly to suit your travel style. With all that extra money, why not throw in some interesting tours and activities? That’s the easiest way to unlock even more discounts. Your dream vacation in Windsor is closer than you thought!
What are the top hotels in Windsor?
Many people traveling to Windsor often stay in Wheatley. Omstead’s On Erie and Blue Butterfly Bed and Breakfast are popular options in this neighborhood. But it’s not the only exciting place in town! South Central is another top area and where you’ll find IACC Centers - Hotel Downtown Windsor and Bexon Rooms - Hotel Downtown Windsor.
When is the best time of year to visit Windsor?
If your definition of “best” means when you’ll get the best deals, pack your bags and head for Windsor in March. By contrast, November is the most expensive month to take a break here. Peak season falls in July, August, June and is an exciting time to visit — but be prepared for bigger crowds and longer queues. October, December, November is usually a quieter time of the year.
How far in advance should I book my Windsor vacation?
It depends on the air carrier, but you can normally compare international fares on Expedia up to a year in advance. While it’s a good idea to book ahead of time, lucky travelers will occasionally score a cheaper ticket just weeks prior to departure dates.
What does an Expedia Windsor travel package include?
From airfares and hotels to car rentals, Expedia can help you shape a Windsor package that’s perfect for you. Vacationing for a week or longer? Check out a hotel, flight and rental car bundle. If you’re taking a quick break, a flight and hotel deal may suit you better. Tours and activities can be added after you’ve booked. Our vacation packages make it a breeze to plan and save.
What should I know before booking a Windsor travel package?
Our prices are always low. However, you’ll pick up an even better deal when you book your hotels, flights and car rentals together. With an Expedia travel package, you’ll always get transparent pricing and loads of choice.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
With one of our vacation packages, you can customize both your trip and a payment plan. Expedia can help reduce financial stress relating to your journey with a Book Now, Pay Later solution, thanks to our proud partnership with online lender Affirm. That way, all you have to concentrate on is preparing to take to the skies.
Can I choose my airline with a Windsor Expedia vacation package?
Yes, the choice is yours. We have access to over 550 partner airlines globally, so you can tailor your Windsor getaway according to your budget and needs.

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