Windermere Vacations from ₩401,460

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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
per person
Oct 8 - Oct 11
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Orlando (MCO)
8.2/10 Very Good! (5,140 reviews)
Found cockroaches in the bathroom. Housekeeping never came to clean the room.

Reviewed on Aug 7, 2025

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
Oct 8 - Oct 11
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Orlando (MCO)
8.2/10 Very Good! (5,190 reviews)
Stay was amazing, property was nice

Reviewed on Aug 7, 2025

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
per person
Oct 8 - Oct 11
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Orlando (MCO)
8.8/10 Excellent! (3,024 reviews)
Property was clean and quiet. Staff was friendly and nice

Reviewed on Aug 6, 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
per person
Sep 14 - Sep 17
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.6/10 Exceptional! (1,000 reviews)
Excelente, buen hotel

Reviewed on Aug 6, 2025

Club Wyndham Bonnet Creek

Club Wyndham Bonnet Creek

3.5 out of 5
per person
Sep 14 - Sep 17
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)
Clean Convenient Large space perfect for groups Lots of pool and food options

Reviewed on May 22, 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 ₩135,908 per night from Aug 17 to Aug 18
₩135,908
₩152,895 total
Aug 17 - Aug 18
includes taxes & fees
8.2/10 Very Good! (6,506 reviews)
"Everything is good except refrigerator is not cold enough."

Reviewed on Aug 7, 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 ₩106,385 per night from Aug 18 to Aug 19
₩106,385
₩119,685 total
Aug 18 - Aug 19
includes taxes & fees
8.4/10 Very Good! (4,743 reviews)
"Great"

Reviewed on Aug 7, 2025

Rosen Inn at Pointe Orlando
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is ₩213,352 per night from Aug 13 to Aug 14
₩213,352
₩240,021 total
Aug 13 - Aug 14
includes taxes & fees
8.8/10 Excellent! (5,123 reviews)
"Good !!!"

Reviewed on Aug 5, 2025

Universal's Cabana Bay Beach Resort
See all 50,878 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 ₩401,460 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.