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.
Seasons Florida Resort
Price was CA $1,100, price is now CA $674 per person
CA $674
per person
Aug 24 - Aug 31
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Orlando (MCO)
9/10 Wonderful! (3,579 reviews)
I loved coming in to a super clean room. With easy check in process and an amazing parking lot with tons of spaces. Amazing stay for the price!!
Reviewed on Jun 9, 2026
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Price was CA $1,117, price is now CA $689 per person
CA $689
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9/10 Wonderful! (1,261 reviews)
Our stay was very pleasant, staff very polite! Great price!
Reviewed on Jun 1, 2026
Windsor Hotel Deals
DoubleTree by Hilton Gainesville
3726 Sw 40th Blvd Gainesville FL
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Jun 15 to Jun 16
CA $135
CA $152 total
Jun 15 - Jun 16
includes taxes & fees
8/10 Very Good! (1,013 reviews)
"Staff were courteous, facilities cl an and modern, and food was good.,"
Reviewed on Jun 6, 2026
Sleep Inn & Suites University/Shands
4110 SW 40th Boulevard Gainesville FL
Fully refundable
The price is CA $99 per night from Jun 30 to Jul 1
CA $99
CA $119 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (1,204 reviews)
"Besides positive things, I did encounter some uneasy things: 1) I was charged a so-called 'expedia' fee. I don't understand because I pre-paid the room cost. The front desk didn't even want to explain why this was done so because I booked the room from hotels.com; 2) I was told that the checkout ..."
Reviewed on Jun 8, 2026
Drury Inn & Suites Gainesville
4000 Southwest 40th Blvd Gainesville FL
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Jun 15 to Jun 16
CA $146
CA $165 total
Jun 15 - Jun 16
includes taxes & fees
9.6/10 Exceptional! (1,471 reviews)
"Property was in a great area but very noisy. Lots of noise from street especially if you like to sleep in. Coffee was really bad, I usually love Drury Coffee but had to go out every day to purchase elsewhere. My room was next to the housekeeping room and they were extremely loud talking in the morning ..."
Reviewed on Jun 5, 2026
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.
What to do in Windsor
Interlachen: Rodman Reservoir Trophy Bass Fishing Trip
CA $602
per adult
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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.
