How much does a Windermere vacation package cost?

You'll find cheap prices from $286 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.

Discover Windermere Vacation Packages for 2026

Name: Orlando International Drive North Hotel
Price range: $82 total
Rating: 7.2

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.

Westgate Vacation Villas Resort

$286

per person

Mar 26 - Mar 31

found 19 hours ago

Roundtrip flight included

New York (LGA) to Orlando (MCO)

8/10 Very Good! (1,703 reviews)

The place was great and convenient to everything

Reviewed on Jan 15, 2026

Residence Inn by Marriott Daytona Beach Oceanfront

$923

per person

Feb 26 - Mar 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

8.6/10 Excellent! (1,002 reviews)

Staff very friendly. Spacious room. Great view. Our room was not cleaned everday, don't know if they were too busy. We did get service when we asked.

Reviewed on Dec 29, 2025

Westgate Town Center Resort

$331

per person

Feb 26 - Mar 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

8/10 Very Good! (1,367 reviews)

We stayed in Building 5100, Room A, and had a mixed experience. Pros: The room was spacious and comfortable with a full kitchen, dining table, separate living area, bedroom, and a bathroom with a hot tub. The location was excellent, close to the Disney parks, with plenty of parking and low noise levels. The pool near our building was clean with great hours. The main resort pool with the lazy river and slides was fun, and Javier the security guard was attentive, polite, and friendly. The Mexican restaurant on site had good food, drinks, and service. Check in and check out were easy. Cons: Cleanliness and service were disappointing. Upon arrival, we found a clipped fingernail in our bed. We called room service at 4:00 pm, but no one arrived until nearly 10:00 pm after multiple calls. We also requested room cleaning for the next day, which was approved, but the room was never cleaned. Water pressure in the bathroom was very poor. Paying extra to access the main resort pool felt unreasonable, especially since it closed for cleaning for almost an hour and a half, leaving limited time before closing. Bar drinks were good, but lines were long due to only two bartenders, and the second floor bar never opened, forcing guests downstairs. Overall, the room and location were strong, but service issues and extra fees negatively impacted our stay.

Reviewed on Jan 10, 2026

Westgate Towers Resort

$315

per person

Feb 26 - Mar 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

8.6/10 Excellent! (1,002 reviews)

Definitely recommend. We stay here every time we come to Orlando very nice.

Reviewed on Jan 18, 2026

Westgate Cocoa Beach Resort

$1,007

per person

Feb 22 - Feb 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

8.8/10 Excellent! (500 reviews)

Everything was great! Staff were super!!

Reviewed on Dec 22, 2025

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Windermere Hotel Deals

DoubleTree by Hilton Hotel Orlando at SeaWorld

10100 International Drive Orlando FL

Fully refundableReserve now, pay when you stay

$99 nightly

$112 total

Feb 8 - Feb 9

Total with taxes and fees

7.4/10 Good! (6,397 reviews)

Clean room nice

Reviewed on Jan 17, 2026

Rosen Inn at Pointe Orlando

9000 International Drive Orlando FL

Fully refundableReserve now, pay when you stay

$76 nightly

$86 total

Feb 8 - Feb 9

Total with taxes and fees

8.4/10 Very Good! (5,549 reviews)

Very CLEAN room!

Reviewed on Jan 17, 2026

Orlando International Drive North Hotel

5859 American Way Orlando FL

Fully refundableReserve now, pay when you stay

$72 nightly

$82 total

Jan 21 - Jan 22

Total with taxes and fees

7.2/10 Good! (2,651 reviews)

Breakfast was better than expected. Staff was friendly. I would book again, but will ask for a cleaner room.

Reviewed on Jan 13, 2026

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, Florida, is a fantastic destination for families and outdoor enthusiasts alike, offering a variety of activities such as golfing, shopping, and enjoying resort amenities. Visitors can explore day trips and sightseeing tours to experience the area's natural beauty and attractions. With expert guides available, you can craft the perfect itinerary to make the most of your stay in this charming community.

Shopping

For a delightful shopping experience in Windermere, visit the Orlando International Premium Outlets, just 5 miles away, and explore a mix of entertainment and family-friendly vibes. Pointe Orlando and the Mall at Millenia, both 6 miles away, offer similar attractions. If you're up for a drive, consider other local options.

Recreation

Experience the energetic atmosphere at the Kia Center, just 10 miles away, perfect for sports enthusiasts. Enjoy a day of golfing at Shingle Creek Golf Course, 8 miles out, surrounded by nature. For family fun, visit Pirate's Cove Adventure Golf, 5 miles away, blending adventure and amusement.

Adventure

Experience the thrills at Universal’s Volcano Bay, a vibrant waterpark 4 miles from Windermere, offering exciting water attractions for the whole family. Enjoy stunning views from The Orlando Eye at ICON Park, located 5 miles away, or unleash your competitive spirit at Wonderworks, an arcade adventure zone 6 miles away.

Nightlife

Windermere's nightlife offers a relaxed charm with cozy bars and delightful dining. Visit the Windermere Wine & Beer Bar for a diverse selection of drinks. For a lively atmosphere, check out local restaurants featuring live music and outdoor seating, perfect for enjoying Florida's warm evenings.

*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 outdoor vacations with plenty of entertainment options. Visitors can enjoy a variety of attractions, including theme parks, scenic lakes, and golf courses. Explore Lake Windermere for a relaxing day on the water, or take advantage of the area's cultural experiences and outdoor activities. This charming destination offers something for everyone, making it an ideal spot for a memorable getaway.

Walt Disney World® Resort: Experience the magic at one of the world's most famous theme parks. With thrilling rides, enchanting parades, and beloved characters, it's a perfect destination for family fun just 6 miles from Windermere.
Orange County Convention Center: Immerse yourself in culture at this vibrant arts center, located 6 miles away. Hosting various events and exhibitions, it’s a hub for creativity and entertainment in the region.
Universal CityWalk: Enjoy a lively atmosphere at this outdoor tourist precinct, only 4 miles from Windermere. With dining, shopping, and entertainment options, it’s an ideal spot for family outings and relaxation.

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

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Windermere.
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.

Language	English
Currency	U.S dollars
Closest Airport	Orlando Intl. Airport (MCO)
Population	3,200
Max Temp Winter	70ºF
Max Temp Summer	90ºF
Top Sights	Walt Disney World® Resort, Universal Orlando Resort and Magic Kingdom® Park

Language

English

Currency

U.S dollars

Closest Airport

Orlando Intl. Airport (MCO)

Population

3,200

Max Temp Winter

70ºF

Max Temp Summer

90ºF