Windsor Hills Vacation Packages

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Top Holiday Package Deals in Windsor Hills

Price found within the past 48 hours. Click for updated prices.
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
per person
Sep 22 - Sep 26
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (5,097 reviews)
The customer service was outstanding and they offer a plethora of activities and amenities.

Reviewed on Jul. 16, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8/10 Very Good! (1,277 reviews)
I love the size of the room very spacious and enough for me and my family

Reviewed on Jul. 15, 2025

ette hotel

ette hotel

5 out of 5
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9.8/10 Exceptional! (313 reviews)
very friendly helpful staff. nice area with many restaurants and grocery stores around. clean rooms. elegant hotel

Reviewed on Jul. 4, 2025

Hilton Daytona Beach Oceanfront Resort

Hilton Daytona Beach Oceanfront Resort

4 out of 5
Brush - Stewarts
Save 100% on your flight
per person
Sep 29 - Oct 6
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Orlando (MCO)
7.4/10 Good! (4,845 reviews)
The property is run down and needs some love!

Reviewed on Jul. 16, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Save 100% on your flight
per person
Sep 22 - Sep 26
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,006 reviews)
Property needs some TLC, outside looks beautiful but the carpeting is old and needs replaced in the towers

Reviewed on Jul. 16, 2025

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
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International Drive District

1 out of top 10 points of interest in this area

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

Find hotels in International Drive District

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)
family vacaction
"nice location, pool felt good after the parks"

Reviewed on Jul. 2, 2025

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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! (138 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

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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
8.8/10 Excellent! (11 reviews)
Very Nice
"Would definitely stay again"

Reviewed on May 6, 2025

Get rates
2Pool Home Water Park Disney 2 m Universal Sea World! By Mystic Dunes golf !
See all 1,818 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Windsor Hills vacation package cost?
Explore the best of Windsor Hills from just CA $509. Choose from a great selection of rental cars, hotels and flights to suit your travel style. You can score even more discounts when you add a few tours or activities to your package.
How do I get a cheap travel package to Windsor Hills?
Our Windsor Hills vacation packages promise plenty of savings for the savvy wanderer. For the best deals, simply combine your flights, hotels and extras (such as activities) into an affordable package. But great bargains are just the beginning of your next awesome adventure. Book with Expedia and you'll have more than 550 air carriers and 1,000,000 hotels worldwide to choose from. Whatever your budget or style, there's a package here just for you.
Where should I stay in Windsor Hills?
If you hope to check out Orange Lake Golf, skip commuting and stay nearby. It's one of the best attractions in this neighborhood.
What are the top hotels in Windsor Hills?
If this will be your first time in Windsor Hills, make a reservation at Luxury 6 Bedroom 4 Bath Villa With South Facing Pool 10 Minutes From Disney or Windsor Hills Villa With Themed Bedrooms 2mi To Disney. Both hotels offer comfy beds and are popular options with lots of travelers.
How far in advance should I book my Windsor Hills vacation?
It can be hard to know when the best time is to book your Windsor Hills trip. But usually the earlier you book, the cheaper the prices. In some cases, you can lock in your flights and hotels nearly a year prior to your departure date. If you're thinking of a last-minute getaway, no need to worry! There are great bargains posted on Expedia every day.
What does an Expedia Windsor Hills travel package include?
You can select from any combination of hotels, flights and rental cars. Once you've made your booking, you can add some experiences and activities. Want to pick your airfare class? That's easily done too. The choice is all yours when it comes to arranging your perfect Windsor Hills trip.
What should I know before booking a Windsor Hills travel package?
A travel package can be customized for your circumstances and is a great way to make your hard-earned dollars stretch further. How little or much you include is completely up to you. Rental cars, hotels and flights --- come up with a combination that suits your plans.
Can I choose my airline with a Windsor Hills Expedia vacation package?
Yes, of course. We have more than 550 partner airlines across the globe, so select the carrier that fits your budget and traveling style.
If I'm not able to travel, can I cancel my Windsor Hills vacation package?
Yes, you can. We understand that even the best-laid plans can fail, so we're here to help if you need to make changes to your Windsor Hills vacation package. It may be possible to cancel or change your itinerary at no cost if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.

Discover the most popular places to visit in Windsor Hills

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(226 reviews)

Walt Disney World® Resort is part of Orlando. It makes up part of bustling metropolis that is home to 240,000 inhabitants. Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando’s city center. If you are flying in, Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando International Airport.

Walt Disney World® Resort
Universal Studios Florida

Universal Studios Florida

4.5/5(988 reviews)

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

Universal Studios Florida
Universal Studios Orlando which includes street scenes, a city and rides

Universal Orlando Resort

4.5/5(399 reviews)

Make your Florida vacation one to remember with a stay at this hotel and theme park complex.

Universal Orlando Resort

Things to do

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Aquatica Orlando

CA $74
per traveller
82% of travellers recommend
Aquatica Orlando
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $108
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Explore the Wonderful World of the Oz Books in a way that you have never seen before...

Wizard of OZ Museum tour

CA $41
per adult
100% of travellers recommend
Wizard of OZ Museum tour
See all activities in Orlando
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.