Windsor Hills Vacations from $248

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon
    Better together
    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Windsor Hills Vacation

Take all the hassle out of planning your next escape with a Windsor Hills vacation package. Take in the sights and sounds of this enticing neighborhood and experience all it has to offer. Eager to sightsee during your trip to Windsor Hills? Be sure to check out nearby attractions like Mystic Dunes Golf Club, Orange Lake Golf and Jack Nicklaus Course. Stop dreaming and start doing. When it's time to book your dream vacation to Windsor Hills, Expedia will help you get there.

The Latest Windsor Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort
Westgate River Ranch Resort & Rodeo
Westgate Palace Hotel / Universal / I-Drive
Ocean Sands Beach Boutique Inn - 1 Acre Private Beach
Westgate Lakes Resort & Spa Universal Studios Area

Where to stay in Windsor Hills

Find the best Windsor Hills areas and neighborhoods for the activities you enjoy most. Learn more about Windsor Hills

Windsor Hills Hotel Deals

6/4 Home Pool/Spa Close to Disney,  Free Water Park Use, Game RMThemed, WIFI BBQ
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Kissimmee
9.2/10 Wonderful! (214 reviews)
Spacious
"The house is very spacious. It has some very good pros and some cons.Pros- Spacious with plenty of room for our party of 12. Nice size kitchen, the bedrooms were good size as was the bathrooms. Comfortable beds and in a very convenient location to all the Disney Parks.Cons- The garage converted to ..."

Reviewed on Jun 1, 2025

6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Magical 4 Bedroom Villa with Private Pool Minutes from Disney! Free Pool Heat!
Magical 4 Bedroom Villa with Private Pool Minutes from Disney! Free Pool Heat!
Kissimmee
9.8/10 Exceptional! (136 reviews)
Epic family fun
"My wife and kids had an absolute blast in this property. Beautiful resort with a water park and so much more. We had a great time. Thank you."

Reviewed on Jun 27, 2025

Magical 4 Bedroom Villa with Private Pool Minutes from Disney! Free Pool Heat!
2Pool Home Water Park Disney 2 m Universal Sea World! By Mystic Dunes golf !
2Pool Home Water Park Disney 2 m Universal Sea World! By Mystic Dunes golf !
Kissimmee
9.4/10 Exceptional! (10 reviews)
Very Nice
"Would definitely stay again"

Reviewed on May 6, 2025

2Pool Home Water Park Disney 2 m Universal Sea World! By Mystic Dunes golf !
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 Hills

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.