Windsor Holidays

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Our guide on where to stay in Windsor

Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
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Walkerville

If you're spending some time in Walkerville, Willistead Manor and Olde Walkerville Neighborhood are top sights worth seeing.

Find hotel + flight trips in Walkerville

Our pick of the best Windsor Hotel Deals

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 NZ$215 per night from 9 Jun to 10 Jun
NZ$215
per night
9 Jun - 10 Jun
8.6/10 Excellent! (1,003 reviews)
"Very nice place, great service!"

Reviewed on 20 May 2024

Holiday Inn Express Windsor Waterfront, an IHG Hotel
Caesars Windsor
Caesars Windsor
4 out of 5
377 Riverside Dr E, Windsor, ON
The price is NZ$227 per night from 9 Jun to 10 Jun
NZ$227
per night
9 Jun - 10 Jun
8.2/10 Very Good! (1,950 reviews)
"The check-in wait was significant. Another employee helping with check-in would have been appreciated. Other than that - the property was beautiful, the service was excellent, and everything was great!"

Reviewed on 20 May 2024

Caesars Windsor
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 NZ$245 per night from 2 Jun to 3 Jun
NZ$245
per night
2 Jun - 3 Jun
7.8/10 Good! (1,008 reviews)
"The staff was beyond helpful and helped provide everything my family needed. The pool was amazing and the whole overall aura of the place was very inviting and chic. Highly recommend, and I hope to be back soon."

Reviewed on 19 May 2024

DoubleTree by Hilton Windsor Hotel & Suites
See all 309 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.

Frequently asked questions

How much does a Windsor holiday package cost?
From as low as , you can customize your Windsor holiday 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 holiday 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 holidaying with the entire family or travelling solo, organising a trip to Windsor is better with a package.
Where should I stay in Windsor?
We recommend staying near the action. Many travellers 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?
Travellers going to Windsor often book Caesars Windsor or Best Western Plus Waterfront Hotel. You’ll find them in Walkerville. Another happening neighbourhood 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 holiday?
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 travelling 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 holiday homes such as mountain cabins and city residences. The list is almost endless!
Can I choose my airline with a Windsor Expedia holiday 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 holiday.
If I'm not able to travel, can I cancel my Windsor holiday package?
Yes you can, and we’ll help you every step of the way. You may be able to cancel or change your Windsor holiday 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

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Caesars Casino

Why not try your luck with a visit to Caesars Casino during your travels in Windsor? Discover the top-notch restaurants and acclaimed theatre scene in this vibrant area.

Caesars Casino
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Caesars Windsor

4/5(1 review)

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

Caesars Windsor
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Windsor Riverfront

After visiting Windsor Riverfront, make a plan to see the other sights and activities in Windsor.

Windsor Riverfront

What to do in Windsor

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Motor City Ghosts Tour

NZ$54
Per adult
Motor City Ghosts Tour
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Roasting Experience at 14th Coffee Co

NZ$114
Per adult
Roasting Experience at 14th Coffee Co
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Detroit: Architectural Beauty and Hidden Gems Walking Tour

NZ$211
Per adult
Detroit: Architectural Beauty and Hidden Gems Walking Tour
See all activities in Windsor

More holiday ideas

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