Windsor Hills Vacation Packages 2026 from $245

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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 Towers Resort

Save 100% on your flight

$245

per person

Oct 1 - Oct 5

found 2 days ago

Roundtrip flight included

San Juan (SJU) to Orlando (MCO)

8.6/10 Excellent! (1,004 reviews)

Great room and view of fireworks.

Reviewed on Aug 28, 2026

Palazzo Lakeside Hotel

$333

per person

Oct 18 - Oct 24

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

8.4/10 Very Good! (5,311 reviews)

Westgate Leisure Resort

International Drive District

Save 100% on your flight

$367

per person

Nov 3 - Nov 9

found 16 hours ago

Roundtrip flight included

San Juan (SJU) to Orlando (MCO)

8.4/10 Very Good! (1,000 reviews)

Naaaaaaaa

Reviewed on Aug 7, 2026

The Delaney Hotel

South Orange

Save 100% on your flight

$999

per person

Nov 5 - Nov 8

found 2 days ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

9.6/10 Exceptional! (1,203 reviews)

A place to stay in the medical area off downtown. Not a great place to stay if you are trying to see downtown. Staff is super helpful and nice however. If getting surgery or treatment, not a better option.

Reviewed on Aug 29, 2026

Westgate Town Center Resort

$362

per person

Oct 6 - Oct 11

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

8.2/10 Very Good! (1,934 reviews)

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

A traditional Japanese torii gate with a dragon sculpture in front, overlooking a calm lake with a distant view of a spherical building.

Bay Lake

4 out of top 10 points of interest in this area

Home to all four Walt Disney World Resort theme parks and one water park, this city offers endless entertainment, including Disney's Fort Wilderness Resort & Campground and Magnolia and Palm Golf Courses.

A theme park with a large rock formation, Old-Town sign, and various food and restaurant signs.

International Drive District

Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.

A golf course with sand bunkers, a water hazard, and a clubhouse in the background.

Reunion

The waterparks and pristine golf courses are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.

A city skyline with modern buildings, a lake with swans, and a fountain.

Florida Center

3 out of top 10 points of interest in this area

While visiting Florida Center, you might make a stop by sights like Universal Orlando Resort and Universal Studios Florida.

A large Ferris wheel with blue lighting, surrounded by a parking lot and buildings.

Champions Gate

Abundant dining options and pristine golf courses are well-reviewed features of Champions Gate. Make a stop by top sights like ChampionsGate Golf Club while you're exploring the area.

Windsor Hills Hotel Deals

🌴Beautiful home in Windsor Hills Resort -Disney 2.5 miles 🌴

Kissimmee FL

9.8/10 Exceptional! (200 reviews)

"Great space for family!"

Reviewed on Aug 8, 2026

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6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ

Kissimmee FL

9.4/10 Exceptional! (271 reviews)

"The house was as described in the listing. We had a party of 13 and everyone had a place to sleep and eat. Check-in and check-out were easy and we were close to everything we needed."

Reviewed on Aug 9, 2026

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Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8

Kissimmee FL

9.2/10 Wonderful! (162 reviews)

"The property, the home, the amenities and the staff were all excellent. Check in was a breeze and the communication with the host was quick, clear and positive. The home was everything it was described to be with some of the cutest decorative touches I’ve ever seen."

Reviewed on Jul 29, 2026

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See all 1,771 properties in Windsor Hills

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.