Windermere Packages (Flight + Hotel)

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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 ฿7,423 per night from 25 Nov to 26 Nov
฿7,423
฿8,351 total
25 Nov - 26 Nov
includes taxes & fees
Hyatt Regency Orlando International Airport
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
The price is ฿3,756 per night from 30 Nov to 1 Dec
฿3,756
฿4,226 total
30 Nov - 1 Dec
includes taxes & fees
9.2/10 Wonderful! (7,210 reviews)
"Clean spacious rooms with a kitchen and living space. Perfect for us!!!"

Reviewed on 31 Oct 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/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 ฿3,239 per night from 28 Nov to 29 Nov
฿3,239
฿3,644 total
28 Nov - 29 Nov
includes taxes & fees
Marriott's Grande Vista
See all 56,211 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.

Stay near popular Windermere attractions

Tibet Butler Preserve

Explore 3.6 miles of trails through Florida's diverse ecosystems at this tranquil preserve near Orlando. The Vera Carter Environmental Centre offers fascinating exhibits about local wildlife and habitats.
See properties

What to do in Windermere

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

฿1,113
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

฿4,622
per adult
78% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

฿1,031
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
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.