Windermere Vacations from ₩413,856

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The Latest Windermere Vacation Packages

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

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Orlando (MCO)
8.2/10 Very Good! (5,163 reviews)
Staff very nice. Overall great stay for 5 days

Reviewed on Aug 12, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Orlando (MCO)
8/10 Very Good! (1,328 reviews)
The property was great the first room given was not the best but the property rectified the situation asap and I was moved to another awesome room

Reviewed on Aug 11, 2025

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Orlando (MCO)
8.8/10 Excellent! (3,037 reviews)
Hotel was comfortable. Several restaurants within walking distance. Used the public transportation to get around the area.

Reviewed on Aug 9, 2025

ette hotel

ette hotel

5 out of 5
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Orlando (MCO)
9.8/10 Exceptional! (325 reviews)
Excellent service, food, location and staff! Thank you

Reviewed on Aug 11, 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Save 100% on your flight
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Orlando (MCO)
9.6/10 Exceptional! (1,000 reviews)
Excellent, loved the location and atmosphere, also the free parking was a nice bonus

Reviewed on Aug 10, 2025

Find the Best Windermere Vacation Packages

Windermere Hotel Deals

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is ₩136,508 per night from Aug 18 to Aug 19
₩136,508
₩153,572 total
Aug 18 - Aug 19
includes taxes & fees
8.4/10 Very Good! (6,528 reviews)
"I like everything"

Reviewed on Aug 10, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is ₩106,855 per night from Aug 26 to Aug 27
₩106,855
₩120,214 total
Aug 26 - Aug 27
includes taxes & fees
8.4/10 Very Good! (4,783 reviews)
"My room key stopped working and I'd left my car keys inside, I'd had to walk all the way (they'd put me in Building F) across the campus which is a long way, security let me back into my room. What a hassle. The night time desk staff were kind of just.. meh about their job and it showed in the level ..."

Reviewed on Aug 12, 2025

Rosen Inn at Pointe Orlando
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is ₩121,341 per night from Sep 2 to Sep 3
₩121,341
₩136,508 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (2,813 reviews)
"Staff was super friendly , asked for extra bedding and they responded quickly. Beautiful place."

Reviewed on Aug 10, 2025

Marriott's Grande Vista
See all 52,295 properties in Windermere
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 Windermere

Walt Disney World® Resort

Walt Disney World® Resort

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

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

Universal Studios Florida
Universal Studios Orlando showing street scenes, a city and rides

Universal Orlando Resort

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

Universal Orlando Resort

Frequently asked questions

How much does a Windermere vacation package cost?
You'll find cheap prices from ₩413,856 on Expedia for your Windermere getaway. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Windermere costs.
What are the cheapest months to go to Windermere?
Plan your trip for the off-peak season and you're likely to get cheap Windermere vacation packages. Bear in mind that public holidays and local events and festivals can have an impact on prices, so do some research before booking.
How many days is enough for Windermere?
Windermere vacations can be short or long, but to really sink your teeth into this destination, we reckon 3 days is a good ballpark. This will mean you can fit in top attractions like Windermere Country Club and Windermere Country Club and seek out some hidden gems. Don't forget to explore neighborhoods such as Florida Center and Lake Buena Vista North either. If you're smart with your time, you can even schedule a day trip or two from Windermere too.
Is it worth booking a vacation package to Windermere?
Windermere is a good vacation destination with attractions like Isleworth Golf and Country Club among the many things to keep you entertained. Whether you're traveling with the family or getting away with friends, a Windermere vacation promises a good time for everyone.
How to find the best Windermere package deals?
Use Expedia's handy filters to help you find some tempting Windermere package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Windermere package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Windermere vacation as a package?
You can enjoy significant savings on your Windermere getaway by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to see the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Windermere?
If you have your Windermere vacation dates confirmed, book as soon as you can to snap up some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Windermere?

  1. Choose your dates: What you want to do in Windermere and your preferred season will help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to cover everything from food and transportation to activities and airfares. Your accommodations will likely be the largest expense during your trip to Windermere.
  3. Decide your trip length: Think about how much time you'd like to spend exploring Windermere. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a tailored Windermere vacation package.

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