Windsor Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Your Windsor Vacation

Take the stress out of organizing your next exciting adventure with a Windsor vacation package. Whether you're lured here by its history, food or other highlights, this city offers endless possibilities for fun. Every trip to Windsor should include a little sightseeing. Kates Fish Camp is an excellent place to start. No matter your travel plans or budget, organizing a tailored Windsor vacation is a cinch with Expedia.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was CA $1,832, price is now CA $639 per person
CA $639
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very good! (5,252 reviews)

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
International Drive District
Price was CA $1,542, price is now CA $903 per person
CA $903
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
7.8/10 Good! (553 reviews)
Everything was amazing. Thank you!

Reviewed on Jul 24, 2026

WorldQuest Orlando Resort

WorldQuest Orlando Resort

4 out of 5
Price was CA $1,642, price is now CA $1,039 per person
CA $1,039
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Orlando (MCO)
8.4/10 Very good! (4,083 reviews)
Place was ok if all you’re going to do is sleep. There were a lot of issues with our room. Shower door was broke in Master bedroom and wouldn’t close. Ceiling fans were broke, couch was broke and sunk in so bad you couldn’t even sit on it. Property is older and run down. I would spend the extra money and upgrade to the renovated rooms. Unfortunately we will never stay here again but if all you’re doing is sleeping price was decent

Reviewed on Jul 19, 2026

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $1,348, price is now CA $861 per person
CA $861
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9/10 Wonderful! (1,287 reviews)
Everything was very clean and we had great time

Reviewed on Jul 23, 2026

Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was CA $1,329, price is now CA $858 per person
CA $858
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Orlando (MCO)
8.6/10 Excellent! (1,003 reviews)
The 2 bed villa was perfect sized for my party. I really enjoyed having a full sized kitchen to make meals and relax. The room was super clean. The staff was absolutely fantastic.

Reviewed on Jul 24, 2026

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Windsor Hotel Deals

HOM Hotel Gainesville, SureStay Collection by Best Western

HOM Hotel Gainesville, SureStay Collection by Best Western

2.5 out of 5
3905 Sw 43Rd St Gainesville FL
Fully refundableReserve now, pay when you stay
The price is CA $113 per night from Jul 26 to Jul 27
CA $113
CA $128 total
Jul 26 - Jul 27
includes taxes & fees
HOM Hotel Gainesville, SureStay Collection by Best Western
Drury Inn & Suites Gainesville

Drury Inn & Suites Gainesville

3 out of 5
4000 Southwest 40th Blvd Gainesville FL
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Aug 10 to Aug 11
CA $148
CA $166 total
Aug 10 - Aug 11
includes taxes & fees
Drury Inn & Suites Gainesville
Sleep Inn & Suites University/Shands

Sleep Inn & Suites University/Shands

2.5 out of 5
4110 SW 40th Boulevard Gainesville FL
Fully refundable
The price is CA $113 per night from Aug 25 to Aug 26
CA $113
CA $135 total
Aug 25 - Aug 26
includes taxes & fees
Sleep Inn & Suites University/Shands
See all 868 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Windsor

Interlachen: Rodman Reservoir Trophy Bass Fishing Trip

Interlachen: Rodman Reservoir Trophy Bass Fishing Trip

CA $617
per adult
Interlachen: Rodman Reservoir Trophy Bass Fishing Trip
See all activities in Windsor

Frequently asked questions

How much does a Windsor vacation package cost?
We make it easy for everyone to travel, with Windsor vacation packages starting from as low as CA $639. You'll have the flexibility to combine your favorite hotels, airlines and car rental. For the ultimate escape, why not add a few activities and tours to your itinerary?
How do I get a cheap travel package to Windsor?
Imagine all the thrilling things you could do in Windsor with a wad of extra cash in your wallet. Watch your savings stack up when you bundle your airfare and hotel bookings into a Windsor vacation package. You have loads of choice when you book your trip with Expedia too. In fact, you can select from more than 550 airlines and 1,000,000 hotels around the globe. Whether you're taking off with the family or surprising your special someone, planning a getaway to Windsor is better with a package.
How far in advance should I book my Windsor vacation?
To score discount prices, book as early as you can. Air carriers typically release tickets, along with some of the lowest fares, up to 12 months ahead of time. Hotels, experiences and car rental should also be booked well in advance so you can have the pick of the bunch. If you were hoping for a last-minute getaway in Windsor, there are always lots of great bargains to be had on Expedia. Book something in today!
What does an Expedia Windsor travel package include?
Packages include flights, hotels and rental cars, but you can mix and match them to create your perfect Windsor trip. You can also add on fun things like tours and activities once you've made your booking. You're in charge! When you bundle your bookings with Expedia, you'll get access to deals you won't find elsewhere.
What should I know before booking a Windsor travel package?
Whether it's relaxation or adventure you're seeking, a Windsor vacation package lets you organize your escape your way. Plus, you'll get access to great discounts when you combine your accommodations with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Windsor Expedia vacation package?
Most definitely. Expedia has more than 550 airline partners to select from around the globe. With so many choices, finding the right carrier to whisk you away to Windsor will be a snap.
If I'm not able to travel, can I cancel my Windsor vacation package?
If your vacation plans in Windsor have been upended, it's a relief to know that you can amend or cancel your booking. If your booking was made in the last 24 hours, you may be able to receive a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may charge a cancellation fee. For more details, check our Customer Service Portal.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.