Windsor Hills Packages (Flight + Hotel)

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Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was ฿12,358, price is now ฿10,035 per person
฿10,035
per person
4 Dec - 6 Dec
found 24 hours ago
Return direct flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (5,176 reviews)
Highly recommended, close to all the parks, delicious breakfasts, and a good variety of breakfast options.

Reviewed on 30 Sept 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was ฿16,624, price is now ฿11,929 per person
฿11,929
per person
4 Dec - 6 Dec
found 24 hours ago
Return direct flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (5,346 reviews)
Room was leaking water

Reviewed on 30 Sept 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was ฿17,984, price is now ฿13,628 per person
฿13,628
per person
4 Dec - 6 Dec
found 24 hours ago
Return direct flight included
Boston (BOS) to Orlando (MCO)
9.6/10 Exceptional! (1,003 reviews)
As always my stay was great. The staff was also amazing.

Reviewed on 25 Sept 2025

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was ฿14,023, price is now ฿10,945 per person
฿10,945
per person
4 Dec - 6 Dec
found 24 hours ago
Return direct flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (3,125 reviews)
Extra clean room, convenient laundry area, and wonderful staff. I love the resorts decor!

Reviewed on 30 Sept 2025

DoubleTree by Hilton Orlando Airport

DoubleTree by Hilton Orlando Airport

4 out of 5
Airport North
Price was ฿16,459, price is now ฿13,749 per person
฿13,749
per person
4 Dec - 6 Dec
found 24 hours ago
Return direct flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,752 reviews)
The pool was dirty, and it had a lot of Clorox. Besides that, everything was perfect to my liking.

Reviewed on 30 Sept 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

Top hotels in Windsor Hills

Magical Harry Potter Themed Condo

Magical Harry Potter Themed Condo

3 out of 5
Almaton Loop 2813, Kissimmee, FL
8/10 Very Good! (1 review)
"Overall a great stay. Other people are loud at night in upstairs condos but that’s to be expected. The pool area was great. The store on property was very helpful and well priced. They also have good pizza. My only complaint would be no storage in kids room. We had 4 kids with no place to put ..."

Reviewed on 11 Apr 2025

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Magical Harry Potter Themed Condo
Windsor Hills Getaway 3BR with Pool

Windsor Hills Getaway 3BR with Pool

3 out of 5
7679 Fitzclarence St, Kissimmee, FL
The price is ฿64,436 per night from 2 Oct to 3 Oct
฿64,436
฿73,135 total
2 Oct - 3 Oct
includes taxes & fees
Windsor Hills Getaway 3BR with Pool
See all 1,839 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.

Frequently asked questions

How much does a Windsor Hills holiday package cost?
Explore the best of Windsor Hills from just ฿10,035. 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 holiday 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 neighbourhood.
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 travellers.
How far in advance should I book my Windsor Hills holiday?
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 holiday package?
Yes, of course. We have more than 550 partner airlines across the globe, so select the carrier that fits your budget and travelling style.
If I'm not able to travel, can I cancel my Windsor Hills holiday 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 holiday 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.

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Walt Disney World® Resort

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Universal Studios Florida

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฿3,179
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฿1,650
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.