Windermere Vacations from $316

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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 Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
per person
Jun 6 - Jun 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (1,011 reviews)
Great place to stay.

Reviewed on Apr 28, 2025

Westgate River Ranch Resort & Rodeo

Westgate River Ranch Resort & Rodeo

3.5 out of 5
Save 100% on your flight
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
8/10 Very Good! (322 reviews)
Overall great experience

Reviewed on Apr 22, 2025

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
per person
Jul 9 - Jul 16
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (1,010 reviews)
Check in was do easy. The reception area was very welcoming. The staff was friendly and very helpful

Reviewed on Apr 14, 2025

Garnet Inn & Suites, Orlando

Garnet Inn & Suites, Orlando

2 out of 5
per person
Jun 20 - Jun 22
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
6.8/10 (2,064 reviews)
The staff was extremely helpful and pleasant.Poor breakfast choices. Can do better.

Reviewed on Apr 28, 2025

Extended Stay America Select Suites - Orlando - Maitland - Summit Tower Blv

Extended Stay America Select Suites - Orlando - Maitland - Summit Tower Blv

2.5 out of 5
per person
Jun 20 - Jun 22
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
6.2/10 (1,003 reviews)
It's pretty basic here. They didn't have an extra set of sheets for the pull out couch for the suite so we went to the front desk to get more, but they didn't have a blanket. I also wish the blanket was thicker. There weren't enough towels, let alone hand towels, for us either. We weren't there long enough for me to take photos, as I was working an event nearby. There also wasn't enough disabled parking available either. Besides those few things, everything else was fine. We checked out before the front desk opened. The room stayed cold. The toilet was quiet. The bed was comfortable. The hotel clerk was also nice. We had a room right by the front desk and exit. People we did see lingering about were nice also. Definitely decent and cheap enough for a night stay.

Reviewed on Apr 28, 2025

Find the Best Windermere Vacation Packages

Windermere Essential Information

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

Ready to book your vacation to Windermere?

 

Choose your dates

Windermere Hotel Deals

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 $104 per night from May 6 to May 7
$104
includes taxes & fees
$93 per night
May 6 - May 7
8.2/10 Very Good! (6,254 reviews)
"The property was very close to Universal Studios with a covered walkway to cross the Main Street and onto Universal's property. The staff was great, very friendly and knowledgeable."

Reviewed on Apr 27, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
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 $213 per night from May 12 to May 13
$213
includes taxes & fees
$189 per night
May 12 - May 13
9.2/10 Wonderful! (3,233 reviews)
"Amazing staff and great location"

Reviewed on Apr 28, 2025

Hyatt Regency Orlando International Airport
DoubleTree by Hilton Hotel Orlando at SeaWorld
DoubleTree by Hilton Hotel Orlando at SeaWorld
4 out of 5
10100 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is $120 per night from May 26 to May 27
$120
includes taxes & fees
$106 per night
May 26 - May 27
7.2/10 Good! (5,924 reviews)
"Good"

Reviewed on Apr 28, 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
See all 52,119 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Windermere vacation package cost?
You’ll find cheap prices from $316 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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 the most popular places to visit in Windermere

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(2,427 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(9,273 reviews)

Thrill rides based on your favorite movies create this internationally acclaimed theme park.

Universal Studios Florida
Disney Springs® showing a river or creek, a bridge and a sunset

Disney Springs™

4.5/5(11,529 reviews)

Families have everything they could want in an area where boredom is absent and plenty of shopping and dining experiences are available.

Disney Springs™

What to do in Windermere

Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

$202
per traveler
86% of travellers recommend
Universal Orlando Resort Express Passes
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

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

$27
per adult
90% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$68
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
See all activities in Windermere

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.