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 Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $1,387, price is now CA $716 per person
CA $716
per person
May 22 - May 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Orlando (MCO)
8/10 Very Good! (1,836 reviews)
I had to wait three hours for check-in didn’t get checked in till 6 o’clock that afternoon . They are over booking and under staff.

Reviewed on Apr 12, 2026

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Price was CA $1,357, price is now CA $758 per person
CA $758
per person
May 22 - May 29
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Yes it did everything was great

Reviewed on Apr 12, 2026

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $1,384, price is now CA $774 per person
CA $774
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (1,554 reviews)
$25 dollars for person to enter the water park. That’s insane.

Reviewed on Apr 12, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,367, price is now CA $772 per person
CA $772
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.4/10 Very Good! (6,071 reviews)
They should offer breakfast. Otherwise, staff was great and amenities were nice.

Reviewed on Apr 12, 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 $1,528, price is now CA $916 per person
CA $916
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,005 reviews)
Its always a pleasure to stay at Westgate Bluetree! Clean rooms and property, friendly staff and very conveniently located near dusney, outlets, grocery stores and more!!

Reviewed on Apr 1, 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 $107 per night from Apr 19 to Apr 20
CA $107
CA $120 total
Apr 19 - Apr 20
includes taxes & fees
8.6/10 Excellent! (1,878 reviews)
Clean room but very basic. Good for the money. Need some updates on window coverings. New shower tiles I think but no shelf to put shampoo on. Beds were fine. Breakfast was normal hotel free breakfast.

Reviewed on Apr 12, 2026

HOM Hotel Gainesville, SureStay Collection by Best Western
Country Inn & Suites by Radisson, Gainesville, FL

Country Inn & Suites by Radisson, Gainesville, FL

3 out of 5
4015 Sw 43rd St Gainesville FL
Fully refundable
The price is CA $122 per night from Apr 19 to Apr 20
CA $122
CA $138 total
Apr 19 - Apr 20
includes taxes & fees
9.2/10 Wonderful! (1,759 reviews)
The staff was very nice but the room was outdated.

Reviewed on Apr 12, 2026

Country Inn & Suites by Radisson, Gainesville, FL
DoubleTree by Hilton Gainesville

DoubleTree by Hilton Gainesville

4 out of 5
3726 Sw 40th Blvd Gainesville FL
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Apr 26 to Apr 27
CA $134
CA $151 total
Apr 26 - Apr 27
includes taxes & fees
7.8/10 Good! (1,006 reviews)
Clean rooms and facilities. Great staff

Reviewed on Apr 8, 2026

DoubleTree by Hilton Gainesville
See all 888 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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Discover the most popular places to visit in Windsor

Shands at the University of Florida

4.5/5(2 reviews)

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

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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.