Windermere Vacation Packages

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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.

Top Windermere Vacation Deals

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

Seasons Florida Resort

2 out of 5
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.8/10 Excellent! (3,037 reviews)
Hotel was comfortable. Several restaurants within walking distance. Used the public transportation to get around the area.

Reviewed on Aug. 9, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
per person
Sep 13 - Sep 17
found 21 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Orlando (MCO)
8.8/10 Excellent! (1,013 reviews)
Serve breakfast buffet for the morning

Reviewed on Aug. 8, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
per person
Oct 25 - Oct 31
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8/10 Very Good! (1,303 reviews)
Great atmosphere for family

Reviewed on Aug. 5, 2025

Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Reunion
per person
Oct 25 - Oct 31
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.8/10 Excellent! (1,369 reviews)
The room was comfortable but very outdated and worn compared to the online photos. For the price, I feel I overpaid. At the pool, there were no beach accessories like floaties, and no pool towels were provided in our room despite being told they would be. There were also no activities for kids at any of the pools. Not to mention, nowhere on Expedia did it list that parking wasn’t included, and I was charged $20 a day upon arrival. Overall, disappointing for the cost.

Reviewed on Aug. 8, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (5,177 reviews)
Need more and better restaurants, overall the stay was great!

Reviewed on Aug. 9, 2025

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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 CA $135 per night from Sep 9 to Sep 10
CA $135
CA $152 total
Sep 9 - Sep 10
includes taxes & fees
8.2/10 Very Good! (6,512 reviews)
"Almost everything about my stay was perfect. Front desk was friendly, warm, and welcoming. My room was clean, fresh in modern. Housekeeping did a wonderful job with the cleanliness of my room. It's a great hotel, and I will definitely book it again when I'm in the area. One small negative detail ..."

Reviewed on Aug. 8, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is CA $94 per night from Aug 10 to Aug 11
CA $94
CA $106 total
Aug 10 - Aug 11
includes taxes & fees
8.4/10 Very Good! (4,743 reviews)
"Great"

Reviewed on Aug. 7, 2025

Rosen Inn at Pointe 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 CA $120 per night from Sep 1 to Sep 2
CA $120
CA $135 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (2,789 reviews)
"Excellent Resort"

Reviewed on Aug. 8, 2025

Marriott's Grande Vista
See all 51,488 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
Family Vacations
Family Vacations

Discover the most popular places to visit in Windermere

Walt Disney World® Resort

Walt Disney World® Resort

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

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

Universal Studios Florida
Universal Studios Orlando which includes street scenes, a city and rides

Universal Orlando Resort

Make your Florida vacation one to remember with a stay at this hotel and theme park complex.

Universal Orlando Resort

What to do in Windermere

Aquatica Orlando

Aquatica Orlando

CA $66
per traveller
82% of travellers recommend
Aquatica Orlando
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $91
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Indoor Karting

Andretti Indoor Karting & Games in Orlando

CA $42
per adult
80% of travellers recommend
Andretti Indoor Karting & Games in Orlando
See all activities in Windermere

Frequently asked questions

How much does a Windermere vacation package cost?
Offering great value package deals from CA $535 on Expedia, you'll be surprised at how little a vacation to Windermere costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Windermere?
The off-season is the best time to visit Windermere if you're hoping to keep costs down. Another tip for scoring cheap Windermere vacation packages? Try to avoid visiting during public holidays and any major festivals or events.
How many days is enough for Windermere?
We'd suggest booking a Windermere vacation for around 3 days. This gives you enough time to visit key attractions such as Magic Kingdom® Park and Orlando International Premium Outlets, as well as explore neighbourhoods like Florida Centre and Lake Buena Vista North. You could even make time for a day trip (or two) outside of Windermere.
Is it worth booking a vacation package to Windermere?
It's no wonder a Windermere vacation is on the to-do list of many travellers. Top attractions like Isleworth Golf and Country Club are just the beginning of things to keep you busy here.
How to find the best Windermere package deals?
Begin your search for a Windermere package deal by entering your travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Windermere package deal straight away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Windermere adventure off to a flying start.
Is it cheaper to book a Windermere vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Windermere vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Windermere?
Secure fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Windermere getaway.
How to plan a trip to Windermere?

  1. Pick your dates: The things you plan to do in Windermere and your preferred season will help you decide when to travel.
  2. Budget wisely: In addition to the cost of your stay, you should consider other expenses too. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Windermere.
  3. Determine how many days away: Start by compiling a list of the sights and activities you want to get to in Windermere. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your accommodations and airfare: Once you've settled on your travel dates and duration, book the perfect Windermere vacation package for you.

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