Windsor Vacation Packages

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Your Windsor Vacation

When you book a vacation package to Windsor, all the organizing is taken care of beforehand. This gives you more time to discover some of the best things about this riverfront city, such as its cosmopolitan vibe, diversity and friendly locals. You'll want to sightsee during your trip to Windsor. Carve out some time for big-name attractions such as Detroit Windsor Tunnel, Caesars Casino and Caesars Windsor. Expedia is here to help you escape your routine. Tailor your vacation to Windsor to suit your travel style, whatever that may look like.

Where to stay in Windsor

Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
Willistead Park Trail Trailhead featuring a park, heritage elements and a house

Walkerville

Heritage precinct with large houses, wide streets, and abundant greenery, Walkerville boasts attractions like Willistead Manor, the Via Rail station, and the recently reopened Old Walkerville Theatre.

Find hotel + flight trips in Walkerville

Windsor Hotel Deals

Caesars Windsor
Caesars Windsor
4 out of 5
377 Riverside Dr E, Windsor, ON
The price is CA $152 per night from Apr. 21 to Apr. 22
CA $152
CA $204 total
includes taxes & fees
Apr 21 - Apr 22
8.4/10 Very Good! (1,888 reviews)
"Clean room"

Reviewed on Apr. 18, 2024

Caesars Windsor
Holiday Inn Express Windsor Waterfront, an IHG Hotel
Holiday Inn Express Windsor Waterfront, an IHG Hotel
2.5 out of 5
33 Riverside Drive East, Windsor, ON
Fully refundable
The price is CA $156 per night from May 2 to May 3
CA $156
CA $184 total
includes taxes & fees
May 2 - May 3
8.6/10 Excellent! (1,002 reviews)
"Good location."

Reviewed on Apr. 17, 2024

Holiday Inn Express Windsor Waterfront, an IHG Hotel
DoubleTree by Hilton Windsor Hotel & Suites
DoubleTree by Hilton Windsor Hotel & Suites
4 out of 5
333 Riverside Dr W, Windsor, ON
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from May 12 to May 13
CA $154
CA $181 total
includes taxes & fees
May 12 - May 13
7.8/10 Good! (1,002 reviews)
"Great location on river. Close to casino and dining."

Reviewed on Apr. 16, 2024

DoubleTree by Hilton Windsor Hotel & Suites
See all 321 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.

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Frequently asked questions

How much does a Windsor vacation package cost?
From as low as , you can customize your Windsor vacation package. Simply bundle flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Windsor?
Just imagine all the wonderful things you could do in Windsor with a wad of extra cash in your pocket. Watch your savings stack up when you bundle your flights and hotel into a Windsor vacation package. You have plenty of choice when you book with Expedia too. In fact, you can pick from more than 550 air carriers and 1,000,000 properties around the globe. Whether you’re vacationing with the entire family or traveling solo, organizing a trip to Windsor is better with a package.
Where should I stay in Windsor?
We recommend staying near the action. Many travelers favor hotels within easy reach of popular sights, such as Detroit Windsor Tunnel, Caesars Casino and University of Windsor.
What are the top hotels in Windsor?
Travelers going to Windsor often book Caesars Windsor or Best Western Plus Waterfront Hotel. You’ll find them in Walkerville. Another happening neighborhood is East Windsor. Hampton Inn & Suites by Hilton Windsor and Holiday Inn Express Windsor Waterfront, an IHG Hotel are popular options in this part of town.
How far in advance should I book my Windsor vacation?
Browse Expedia to compare international fares ASAP. In most cases, you can purchase a ticket up to a year prior to departure. If you can’t see your preferred carrier, or you’ve left things to the last moment, don’t despair. Cheap fares to Windsor sometimes emerge just weeks before the date of departure.
What does an Expedia Windsor travel package include?
It comes down to what you want. If you’re traveling by yourself, you might decide to combine flights and hotels. Bringing the entire family to Windsor? A travel package that includes hotels, flights and rental cars might suit you better. Expedia gives you the flexibility and freedom to customize your travel package.
What should I know before booking a Windsor travel package?
Booking all the parts of your trip together is a simple way to save. Combine your flights, car rentals and hotels into one little package. But it’s not just hotels. Expedia offers all kinds of properties, including vacation rentals such as mountain cabins and city residences. The list is almost endless!
Can I choose my airline with a Windsor Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you certainly can. Just pick your preferred air carrier and put together your ideal Windsor vacation.
If I'm not able to travel, can I cancel my Windsor vacation package?
Yes you can, and we’ll help you every step of the way. You may be able to cancel or change your Windsor vacation package at no cost if you booked in the last 24 hours. But you may be charged a fee by your hotel, airline or car rental company if you booked more than 24 hours ago. If your circumstances suddenly change, browse our Customer Service Portal for further information.

Discover the most popular places to visit in Windsor

Image for Caesars Casino

Caesars Casino

4.5/5(93 reviews)

Why not try your luck with a visit to Caesars Casino during your time in Windsor? Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area.

Caesars Casino
Image for Caesars Windsor

Caesars Windsor

4.5/5(269 reviews)

Why not try your luck with a visit to Caesars Windsor during your visit to Windsor? Stroll along the riverfront or visit the casinos in this vibrant area.

Caesars Windsor
Image for Ambassador Bridge

Ambassador Bridge

1.5/5(3 reviews)

You can learn about the history of Windsor with a visit to Ambassador Bridge. Stroll along the riverfront or experience the great live music in this vibrant area.

Ambassador Bridge

What to do in Windsor

Image for Motor City Ghosts Tour

Motor City Ghosts Tour

CA $45
Per adult
Motor City Ghosts Tour
Image for Detroit: Architectural Beauty and Hidden Gems Walking Tour

Detroit: Architectural Beauty and Hidden Gems Walking Tour

CA $176
Per adult
Detroit: Architectural Beauty and Hidden Gems Walking Tour
See all activities in Windsor

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.