Windermere Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by RoseMary

Top hotels in Windermere

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 2.428.897 ₫ per night from 14 Aug to 15 Aug
2.428.897 ₫
2.732.510 ₫ total
14 Aug - 15 Aug
includes taxes & fees
8.2/10 Very Good! (6,477 reviews)
"the on site stores are extremely expensive however that’s orlando for you but this was the best Doubletree i’ve ever stayed at and i will be making this my hotel in orlando from now on"

Reviewed on 1 Aug 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is 5.740.647 ₫ per night from 6 Aug to 7 Aug
5.740.647 ₫
6.458.359 ₫ total
6 Aug - 7 Aug
includes taxes & fees
9.4/10 Exceptional! (3,432 reviews)
Very convenient
"It's wonderful to be able to check in my rental car, go upstairs and check in at the hotel all at one location. Then board the plane the next morning."

Reviewed on 31 Jul 2025

Hyatt Regency Orlando International Airport
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 2.285.774 ₫ per night from 24 Aug to 25 Aug
2.285.774 ₫
2.571.495 ₫ total
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (2,738 reviews)
"Unit kitchenette very well equipped and supplied"

Reviewed on 2 Aug 2025

Marriott's Grande Vista
See all 52,406 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.

Popular places to visit

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(63 reviews)

Enjoy the rides and games at Walt Disney World® Resort and find out why this is a popular theme park in Lake Buena Vista. Discover the top-notch restaurants and acclaimed theatre scene in this walkable area.

Walt Disney World® Resort
Universal Studios Florida® showing rides, a city and street scenes

Universal Orlando Resort

4.5/5(166 reviews)

Enjoy the excitement at Universal Orlando Resort and find out why this is a popular theme park in Orlando. Visit the shops and top-notch restaurants in this family-friendly area.

Universal Orlando Resort
Disney Springs™

Disney Springs™

4.5/5(322 reviews)

You can find the perfect gifts to bring home when you visit Disney Springs™, a favourite shopping spot in Lake Buena Vista. Experience the acclaimed theatre scene and entertainment choices in this family-friendly area.

Disney Springs™

Frequently asked questions

How much does a Windermere holiday package cost?
You'll find cheap prices on Expedia for your Windermere getaway. However, factors like the season, choice of hotel and length of stay will influence how much your holiday 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 holiday 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 holidays 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 neighbourhoods such as Florida Centre 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 holiday package to Windermere?
Windermere is a good holiday destination with attractions like Isleworth Golf and Country Club among the many things to keep you entertained. Whether you're travelling with the family or getting away with friends, a Windermere holiday 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 holiday package well in advance.
Is it cheaper to book a Windermere holiday as a package?
You can enjoy significant savings on your Windermere getaway by booking a personalised holiday 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 holiday package to Windermere?
If you have your Windermere holiday 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 accommodation 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 holiday package.