Windermere Holidays

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Windermere Holiday

Our pick of the best 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
The price is NZ$158 per night from 28 July to 29 July
NZ$158
28 July - 29 July
includes taxes & fees
8.2/10 Very Good! (6,410 reviews)
"very good food huge pool and close to amusement parks !"

Reviewed on 8 Jul. 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 NZ$381 per night from 16 July to 17 July
NZ$381
16 July - 17 July
includes taxes & fees
9.4/10 Exceptional! (3,363 reviews)
"The room was excellent and the staff was great! The only issue is the parking. It’s actually airport parking, and a little inconvenient to get to. But once there, it’s okay."

Reviewed on 6 Jul. 2025

Hyatt Regency Orlando International Airport
Kompose Boutique Resort at Theme Parks
Kompose Boutique Resort at Theme Parks
4 out of 5
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Fully refundableReserve now, pay when you stay
The price is NZ$168 per night from 7 Aug to 8 Aug
NZ$168
7 Aug - 8 Aug
includes taxes & fees
9.4/10 Exceptional! (517 reviews)
"Property was beautiful. We will be going back next yeargor our vacation."

Reviewed on 6 Jul. 2025

Kompose Boutique Resort at Theme Parks
See all 52,158 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

4.5/5(9 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(48 reviews)

An attraction popular with visitors from around the world, where you can wander through film sets and enjoy the thrills and spills of the rides.

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

Universal Orlando Resort

4.5/5(30 reviews)

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

Universal Orlando Resort

What to do in Windermere

2014_AQ_KatasKookaburraCove_D4D_0772.jpg

Aquatica Orlando

NZ$90
per traveller
82% of travellers recommend
Aquatica Orlando
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

NZ$141
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

NZ$50
per adult
100% of travellers recommend
Wizard of OZ Museum tour
See all activities in Windermere

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.

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