Windsor Vacation Packages

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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.
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,254, price is now CA $575 per person
CA $575
per person
Nov 2 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (5,254 reviews)
I didn't like the pools, the pictures i saw online wasn't what I actually saw in person. I was disappointed. There were no many entertainments at the facility

Reviewed on Aug. 25, 2025

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $2,507, price is now CA $1,055 per person
CA $1,055
per person
Oct 12 - Oct 17
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Orlando (MCO)
8/10 Very Good! (1,675 reviews)
The AC wasn’t working at all real good in VVC 11B, we had call and told them but they never came to check it out.

Reviewed on Aug. 19, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $1,746, price is now CA $795 per person
CA $795
per person
Nov 2 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.8/10 Excellent! (1,002 reviews)
This was a good time!

Reviewed on Aug. 23, 2025

ette hotel

ette hotel

5 out of 5
Price was CA $2,686, price is now CA $1,449 per person
CA $1,449
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
9.8/10 Exceptional! (330 reviews)
Excellent service, food, location and staff! Thank you

Reviewed on Aug. 11, 2025

Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was CA $1,805, price is now CA $1,009 per person
CA $1,009
per person
Oct 12 - Oct 17
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Orlando (MCO)
8.4/10 Very Good! (1,001 reviews)
There was a very shady old looking red car parked outside our windows with loud music playing late into the night our last two nights

Reviewed on Aug. 19, 2025

Ready to book your vacation to Windsor?

 

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Windsor Hotel Deals

Sleep Inn & Suites University/Shands

Sleep Inn & Suites University/Shands

2.5 out of 5
4110 SW 40th Boulevard, Gainesville, FL
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from Aug 31 to Sep 1
CA $112
CA $134 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Great staff, very friendly and helpful front desk. Convenient location."

Reviewed on Aug. 22, 2025

Sleep Inn & Suites University/Shands
DoubleTree by Hilton Gainesville

DoubleTree by Hilton Gainesville

4 out of 5
3726 Sw 40th Blvd, Gainesville, FL
The price is CA $121 per night from Sep 25 to Sep 26
CA $121
CA $136 total
Sep 25 - Sep 26
includes taxes & fees
7.6/10 Good! (1,003 reviews)
"Got here late. They still were able to get dinner for me and give me a glass of wine."

Reviewed on Aug. 21, 2025

DoubleTree by Hilton Gainesville
Hyatt Place Gainesville Downtown

Hyatt Place Gainesville Downtown

3 out of 5
212 SE 1ST STREET,, Gainesville, FL
The price is CA $148 per night from Sep 24 to Sep 25
CA $148
CA $167 total
Sep 24 - Sep 25
includes taxes & fees
9/10 Wonderful! (1,054 reviews)
"Loved it"

Reviewed on Aug. 20, 2025

Hyatt Place Gainesville Downtown
See all 778 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

Discover the most popular places to visit in Windsor

Shands at the University of Florida

Though Shands at the University of Florida might be what brings you to town, perhaps you'll have a chance to explore more of Gainesville while you are here.

Shands at the University of Florida

North Florida Regional Medical Center

Though North Florida Regional Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Gainesville while you are here.

North Florida Regional Medical Center

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 $575. 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.