Windsor Hills Vacation Packages
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Top Windsor Hills vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Westgate Towers Resort
8.6/10 Excellent! (1,004 reviews)
Oct 1 - Oct 5
4 night stay
San Juan (SJU) to Orlando (MCO)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $474, price is now $245 per person
$245
per person
found 1 day ago
Great room and view of fireworks.
Reviewed on Aug 28, 2026
4.0-star property
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
9.2/10 Wonderful! (1,006 reviews)
Nov 5 - Nov 10
5 night stay
Boston (BOS) to Orlando (MCO)
American Airlines • Coach
Orlando (MCO) to Boston (BOS)
Southwest Airlines • Coach
Price was $1,940, price is now $958 per person
$958
per person
found 1 day ago
4.0-star property
Westgate Palace Hotel / Universal / I-Drive
International Drive District
9/10 Wonderful! (1,308 reviews)
Oct 8 - Oct 13
5 night stay
Boston (BOS) to Orlando (MCO)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,214, price is now $606 per person
$606
per person
found 1 day ago
Staff was very friendly and informative. Location was great. I will be staying here again.
Reviewed on Aug 25, 2026
3.5-star property
The Delaney Hotel
South Orange
9.6/10 Exceptional! (1,203 reviews)
Nov 17 - Nov 23
6 night stay
Boston (BOS) to Orlando (MCO)
Southwest Airlines • Non-stop • Coach
Orlando (MCO) to Boston (BOS)
Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,363, price is now $731 per person
$731
per person
found 1 day ago
Great pre-hospital stay.
Reviewed on Aug 26, 2026
4.0-star property
Westgate Vacation Villas Resort
8.2/10 Very Good! (2,052 reviews)
Nov 3 - Nov 7
4 night stay
Boston (BOS) to Orlando (MCO)
Southwest Airlines • Non-stop • Coach
Orlando (MCO) to Boston (BOS)
Breeze Airways • Non-stop • Coach
Save 100% on your flight
Price was $552, price is now $299 per person
$299
per person
found 1 day ago
This is my second time staying here, I definitely will be back. The staff was super helpful with an early check-in rooms were clean. Definitely kid friendly two water parks, two restaurants, movie theater and arcade. Lots to do and 15 minutes from Magic Kingdom.
Reviewed on Aug 28, 2026
Top rated hotels for your Windsor Hills vacation package
🌴Beautiful home in Windsor Hills Resort -Disney 2.5 miles 🌴
Kissimmee FL
0.22 mi from Windsor Hills
Guests of this vacation home enjoy features like an outdoor pool, a gym, and an arcade/game room. Other amenities at this family-friendly vacation home include laundry facilities and a garden.
Pool
Kitchen
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Kissimmee FL
0.2 mi from Windsor Hills
Guests of this vacation home enjoy features like a gym, a hot tub, and an arcade/game room. Other amenities at this family-friendly vacation home include laundry facilities, a garden, and barbecue grills.
Pool
Hot Tub
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.
Things to do
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
$27
per adult
92% of travellers recommend
