Windermere Vacations from ￥250,372
Book a Hotel + Flight or Car together to unlock savings
The Latest Windermere Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hilton Orlando Lake Buena Vista - Disney Springs® Area
￥527,836
per person
Nov 19 - Nov 25
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
8.6/10 Excellent! (1,727 reviews)
My husband wasn’t allowed to check in because the reservation was in my name. I called several Hilton customer service numbers and also messaged the property through the app. The hotel told me there was nothing they could do. The The lines to check in were atrocious, no matter the time of day. And, despite the size of the hotel, there were always only two employees working to check guests in at any given time. The pullout sofa was a complete joke, and using the word sweet to describe that room is a bit of a stretch. Overall, I would not choose this property again.
Reviewed on Sep 5, 2026
Find the Best Windermere Vacation Packages
Windermere Hotel Deals
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
￥32,658
￥36,741 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (4,438 reviews)
"All was awesome! Great for a long or short layover."
Reviewed on Sep 5, 2026
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
￥19,251
￥21,659 total
Sep 29 - Sep 30
includes taxes & fees
Marriott's Grande Vista
5925 Avenida Vista Orlando FL
Fully refundableReserve now, pay when you stay
￥14,876
￥16,734 total
Sep 27 - Sep 28
includes taxes & fees
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 Center offers fascinating exhibits about local wildlife and habitats.
Isleworth Golf and Country Club
This exclusive, members-only sanctuary features an Arnold Palmer-designed championship golf course. Residents enjoy lavish amenities while rubbing shoulders with professional athletes and celebrities who call Isleworth home.
Lake Bessie
Commune with nature and explore the great outdoors at Lake Bessie during your travels in Windermere. Amble around the area's beaches or visit its shops.
What to do in Windermere
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
￥4,365
per adult
92% of travellers recommend
Universal Orlando Resort Express Passes
￥17,048
per traveler
80% of travellers recommend
Frequently asked questions
How much does a Windermere vacation package cost?
You'll find cheap prices from ￥250,372 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?
- Choose your dates: What you want to do in Windermere and your preferred season will help you decide when to travel.
- 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.
- 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.
- 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.
