
Windsor Holidays from NZ$3,848
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The Latest Windsor Holiday Deals
Price found within the past 48 hours. Click for updated prices.


Margaritaville Cottages Orlando with H2O Waterpark by Vstays
per person
4 Oct - 10 Oct
found 7 hours ago
Return flight included
Nelson (NSN) to Orlando (MCO)
9/10 Wonderful! (1,003 reviews)
The best accommodation we have stayed in whilst visiting Central Florida. Houses are large, private pool area & jacuzzi was a bonus. Local area is great for morning walks & feels well maintained. Highly recommended.
Reviewed on 1 Jul. 2025


Conrad Orlando at Evermore
per person
4 Oct - 10 Oct
found 7 hours ago
Return flight included
Nelson (NSN) to Orlando (MCO)
9.4/10 Exceptional! (225 reviews)
The room was immaculate, grounds were outstanding and exceedingly well maintained, and the service was excellent. Any questions we had were immediately answered - the staff is very attentive and works to ensure guests have a 5-star experience. Very impressed! Also - the on-property restaurants were top notch. Food at Sophia's, the Italian restaurant, was phenomenal.
Reviewed on 7 Jul. 2025

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Golden Oak
per person
4 Oct - 10 Oct
found 7 hours ago
Return flight included
Nelson (NSN) to Orlando (MCO)
9.6/10 Exceptional! (855 reviews)
⭐️⭐️⭐️ Beautiful property and excellent service but outrageous pricing and constant construction limit the experience
The Four Seasons Orlando is visually stunning. The facility is immaculate, the grounds are peaceful, and the staff delivers excellent service at every level. The lazy river is relaxing and the entire resort feels high-end and well maintained.
However, the pricing structure makes it difficult to fully enjoy what the resort offers. I paid six thousand dollars for five nights just for the room. On top of that, nearly everything felt like an upcharge. A soda was six dollars, a basic burger was twenty-three dollars, and a couples massage cost seven hundred sixty dollars. Valet parking was sixty dollars per day with no self-parking option available.
There was also daily construction happening next to the resort which was disruptive at times and took away from the relaxing atmosphere. For the price point, I expected a quiet and peaceful experience which this unfortunately was not.
The pool and lazy river close at nine in the evening and the spa shuts down at eight which feels unnecessarily early for a resort in this category. One of the blankets we received had a visible stain. There was no washer or dryer in the room and instead laundry service was offered at twelve to thirty dollars per item which again felt overpriced.
Dining at the on-site restaurants consistently cost two hundred to five hundred dollars for two people per meal. While the service and surroun
Reviewed on 11 Jul. 2025
Windsor Holiday
Our pick of the best Windsor Hotel Deals

hom hotel + suites, Trademark Collection by Wyndham
3905 Sw 43rd St, Gainesville, FL
Fully refundableReserve now, pay when you stay
The price is NZ$143 per night from 20 July to 21 July
NZ$143
20 July - 21 July
includes taxes & fees
8.2/10 Very Good! (1,679 reviews)
"Great"
Reviewed on 14 Jul. 2025

Hyatt Place Gainesville Downtown
212 SE 1ST STREET,, Gainesville, FL
Fully refundableReserve now, pay when you stay
The price is NZ$211 per night from 11 Aug to 12 Aug
NZ$211
11 Aug - 12 Aug
includes taxes & fees
9/10 Wonderful! (966 reviews)
"Great hotel, but parking was very difficult on a Friday night, and the noise level was high. All in all, would stay again, as it was very clean and the staff was wonderful."
Reviewed on 12 Jul. 2025

Country Inn & Suites by Radisson, Gainesville, FL
4015 Sw 43rd St, Gainesville, FL
Fully refundable
The price is NZ$159 per night from 27 July to 28 July
NZ$159
27 July - 28 July
includes taxes & fees
9/10 Wonderful! (1,417 reviews)
"Very nice place, clean"
Reviewed on 9 Jul. 2025
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.
Discover the most popular places to visit in Windsor
Devil's Milhopper Geological State Park
You can take time to visit Devil's Milhopper Geological State Park during your travels to Gainesville. You can attend a sporting event while in the area.
What to do in Windsor
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.