Windermere Holidays

Photo by RoseMary

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Top hotels in Windermere

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 S$257 per night from 22 Jul to 23 Jul
S$257
22 Jul - 23 Jul
includes taxes & fees
9.4/10 Exceptional! (3,392 reviews)
"Great place to stay if flying out early in the morning. Everyone was nice and hotel had a great pool deck area to watch the planes land and take off."

Reviewed on 20 Jul, 2025

Hyatt Regency Orlando International Airport
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 S$122 per night from 10 Aug to 11 Aug
S$122
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very Good! (6,421 reviews)
"H"

Reviewed on 18 Jul, 2025

DoubleTree by Hilton at the Entrance to Universal 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 S$138 per night from 10 Aug to 11 Aug
S$138
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (2,640 reviews)
"They had restaurants not like any other resort I will definitely come again"

Reviewed on 18 Jul, 2025

Marriott's Grande Vista
See all 52,570 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)

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(273 reviews)

Exhilarating rides and world class film sets are brought together to create this outstanding world-renowned theme park.

Universal Studios Florida
Universal Studios Florida® featuring rides, street scenes and a city

Universal Orlando Resort

4.5/5(166 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

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

S$85
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Indoor Karting

Andretti Indoor Karting & Games in Orlando

S$40
per adult
80% of travellers recommend
Andretti Indoor Karting & Games in Orlando
Old Town Kissimmee: Attraction and Meal Combo Offers

Old Town Kissimmee: Attraction & Food/Drink Voucher

S$19
per adult
80% of travellers recommend
Old Town Kissimmee: Attraction & Food/Drink Voucher
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.