How much does a Windermere vacation package cost?

You'll find cheap prices from $192 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?

If you're looking to score a cheap Windermere vacation package, consider visiting in September, October and December. You'll generally find better prices on hotels and airfares during these quieter months — perfect for a budget-friendly break.

How many days is enough for Windermere?

For your Windermere vacation, a few days will be enough to explore the highlights. Make sure to stop by Windermere Country Club — it's one of the top attractions in this destination. If you're after more adventure, consider basing yourself here and setting off on some trips from Windermere.

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?

Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Windermere. Figure out your budget: Ensure you have enough money to cover everything from transportation and food to activities and airfares. Your hotel will probably be the biggest expense during your trip to Windermere. Explore Windermere with our trip planning tool : Gain insights into the top attractions and best hotels for your trip to Windermere. You can also save your favorite locations, collaborate with your group and manage all your plans in one place. Work out your trip length: Consider how much time you'd like to spend exploring Windermere. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Windermere vacation package that brings all your bookings together. Book activities and experiences ahead of time: Whether it's entrance to a big attraction or a day trip, you won't have to worry about missing out on the highlights of Windermere. Find all the incredible things to do in Windermere with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Windermere vacation packages?

Your Windermere getaway should be a relaxing escape from your daily routine, not a reason for money-related stress. So to give you that extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

Windermere Vacation Packages 2025/2026 from $179

Your Windermere Vacation

An easy way to experience this unique city is with a tailor-made Windermere vacation package. Stay in the neighborhood of Ivanhoe Village, which is great for dining, bars and pubs and shopping or choose someplace else — our packages are all about you. Make your trip to Windermere even more enjoyable by including some sightseeing. Universal Studios Florida, Magic Kingdom® Park and Universal’s Islands of Adventure are some of the big attractions you'll want to explore. Browse Expedia's wide range of travel options and begin planning your ideal vacation to Windermere today.

The Latest Windermere vacation packages

Price found within the past 48 hours. Click for updated prices.

Palazzo Lakeside Hotel

$192

per person

Sep 23 - Sep 28

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

8.2/10 Very Good! (5,171 reviews)

Gould be a good idea to provided some info how to open the gate

Reviewed on Aug 24, 2025

Seasons Florida Resort

$276

per person

Oct 30 - Nov 6

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

8.8/10 Excellent! (3,048 reviews)

Super convenient and nice rooms

Reviewed on Aug 24, 2025

Westgate Cocoa Beach Resort

$616

per person

Oct 11 - Oct 15

found 22 hours ago

Roundtrip flight included

New York (NYC) to Orlando (MCO)

8.8/10 Excellent! (481 reviews)

It was a okay stay. Not enough washer and dryers for the whole resort - literally people were hovering over me watching me while trying to dry my clothes after the beach/pool. Rooms are okay. Jacuzzi and pool was nice. Relaxing for the most part, I did like how often we saw security. Not much offered to do besides the pool. Thought there would be more for a resort.

Reviewed on Aug 24, 2025

Westgate Towers Resort

Save 100% on your flight

$422

per person

Oct 8 - Oct 12

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

8.6/10 Excellent! (1,002 reviews)

Great customer service.

Reviewed on Jul 31, 2025

Westgate Blue Tree Resort in Lake Buena Vista

Save 100% on your flight

$411

per person

Oct 1 - Oct 8

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

8.4/10 Very Good! (998 reviews)

There was a very shady old looking red car parked outside our windows with loud music playing late into the night our last two nights

Reviewed on Aug 19, 2025

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Windermere Hotel Deals

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd, Orlando, FL

Fully refundableReserve now, pay when you stay

$93 nightly

$104 total

Sep 10 - Sep 11

Total with taxes and fees

8.2/10 Very Good! (6,552 reviews)

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Reviewed on Aug 23, 2025

Marriott's Grande Vista

5925 Avenida Vista, Orlando, FL

Fully refundableReserve now, pay when you stay

$87 nightly

$98 total

Sep 14 - Sep 15

Total with taxes and fees

8.8/10 Excellent! (2,925 reviews)

"Excellent place great customer service and Beautiful room clean, spacious, overall excellent quality love the pool. Would recommend it also definitely going again.."

Reviewed on Aug 24, 2025

Rosen Inn at Pointe Orlando

9000 International Drive, Orlando, FL

Fully refundableReserve now, pay when you stay

$60 nightly

$68 total

Aug 27 - Aug 28

Total with taxes and fees

8.4/10 Very Good! (4,815 reviews)

"I loved staying at this property. We stayed for a weekend while we visited Orlando. The room was clean, and the view was spectacular from the top floor. Loved the pool, will visit again!"

Reviewed on Aug 24, 2025

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.

Things to do near Windermere

Windermere offers a perfect blend of family-friendly activities and outdoor fun, featuring resorts, shopping areas, and golf courses. Visitors can enjoy day trips and sightseeing tours led by expert guides, ensuring a memorable experience. Whether you're looking for relaxation or adventure, Windermere has something for everyone to enjoy.

Shopping

If you're up for a drive, visit the Orlando International Premium Outlets, just 5 miles away, featuring a variety of shops and entertainment options. Additionally, Pointe Orlando and Mall at Millenia, both 6 miles away, offer a vibrant shopping atmosphere with numerous dining and entertainment choices.

Recreation

Experience the vibrant atmosphere at Kia Center, just 10 miles from Windermere, perfect for sports enthusiasts. Enjoy a round at Shingle Creek Golf Course, 8 miles away, surrounded by nature. For family fun, visit Pirate's Cove Adventure Golf, only 5 miles from Windermere, offering adventure and excitement for all ages.

Adventure

At Universal’s Volcano Bay, 4 miles from Windermere, experience thrilling water rides and a relaxing lazy river amidst a tropical paradise. The Orlando Eye at ICON Park, 5 miles away, offers breathtaking views from its giant ferris wheel, perfect for family adventures. Wonderworks, 6 miles distant, combines fun and education in an exciting arcade adventure zone.

Nightlife

Windermere offers a cozy nightlife experience with charming venues like the Windermere Brewing Company for craft beers and the nearby Chef's Table for exquisite dining. For a relaxed evening, enjoy the lakeside views at local bars, perfect for unwinding under the stars.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Windermere

Windermere, Florida, is perfect for family-friendly and outdoor vacations, offering attractions like theme parks, scenic lakes, and golf courses. Visitors can enjoy a variety of experiences that cater to family, outdoor enthusiasts, and those seeking cultural adventures. Be sure to explore Lake Windermere for a memorable visit filled with fun and relaxation.

Walt Disney World® Resort: Experience the magic of this iconic theme park, located 6 miles from Windermere. With enchanting rides, vibrant parades, and beloved characters, it's a perfect destination for families looking to create unforgettable memories.
Orange County Convention Center: Situated 6 miles away, this arts center showcases a rich tapestry of culture through various events and exhibitions. Explore the artistic vibe and enjoy a range of performances and conventions that celebrate creativity.
Universal CityWalk: Just 4 miles from Windermere, this lively tourist precinct offers outdoor dining, shopping, and entertainment. It's an ideal spot for families to relax and enjoy vibrant nightlife, live music, and exciting attractions.

Best time to go to Windermere

The best time to visit Windermere can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windermere falls in August, when visitor numbers are average and weather is mostly sunny with moderate rain. The coolest average temperature in Windermere falls in January, visitor numbers are average and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	60.3°F (15.7°C)	Light Rain	Mostly Sunny	Average	Average
February	64.2°F (17.9°C)	No Rain	Mostly Sunny	Average	Average
March	67.5°F (19.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
April	72.5°F (22.5°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
May	77.0°F (25.0°C)	Light Rain	Mostly Sunny	Average	Average
June	80.8°F (27.1°C)	Light Rain	Mostly Sunny	Average	Average
July	82.2°F (27.9°C)	Moderate Rain	Mostly Sunny	Slightly High	Average
August	82.4°F (28.0°C)	Moderate Rain	Mostly Sunny	Average	Slightly Low
September	80.2°F (26.8°C)	Light Rain	Mostly Sunny	Slightly High	Slightly Low
October	75.0°F (23.9°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	68.2°F (20.1°C)	No Rain	Mostly Sunny	Slightly Low	Slightly Low
December	64.0°F (17.8°C)	No Rain	Mostly Sunny	Slightly Low	Slightly High

Tips to save on your trip to Windermere

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling to Windermere during the low season (August to September and November) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.