Windermere Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
per person
Aug. 2 - Aug. 9
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Orlando (MCO)
8/10 Very Good! (3,949 reviews)
Fui con mi familia y nos encantó el servicio por completo. Los empleados bien atentos, el desayuno muy rico y las habitaciones son muy cómodas y limpias. Muchas gracias por todo!!

Reviewed on May 30, 2024

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
Save 100% on your flight
per person
Jul. 7 - Jul. 14
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Orlando (MCO)
8.4/10 Very Good! (999 reviews)
Nice stay but there is housekeeping

Reviewed on May 30, 2024

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
per person
Aug. 21 - Aug. 28
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Orlando (MCO)
7.8/10 Good! (3,685 reviews)
Garbage bag out the door rooms torn by rodents

Reviewed on May 31, 2024

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
per person
Aug. 2 - Aug. 9
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Orlando (MCO)
7.6/10 Good! (1,131 reviews)
It is an awesome resort at a great price. It is set as a 2 star hotel but it has a 4 star for us. They also have a "ride" service that we could request by phone from the room to visit other areas of the resort if you do not wish to walk. The staff is great! They are always ready to assist with a smile. We enjoyed the safety in the facility and with the lifeguards in every corner of the waterpark to make it safe for the kids an all in every ride. Frontdesk started the amazing experience with great customer service and always listening to take our request into consideration. Thank you guys!

Reviewed on May 30, 2024

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
per person
Aug. 2 - Aug. 9
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Orlando (MCO)
8.8/10 Excellent! (1,845 reviews)
its location and the quietness

Reviewed on May 29, 2024

Windermere Hotel Deals

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 CA $109 per night from Jun. 6 to Jun. 7
CA $109
CA $161 total
includes taxes & fees
Jun 6 - Jun 7
7/10 Good! (8,796 reviews)
"Property was nice but the customer service was the best part diego at the front desk was an amazing help and so was everyone else the parking was a lottle bit of a headache there was nothing available and it was 30$ a night but when i talked to them at the front desk they waived the fee thats why ..."

Reviewed on May 28, 2024

DoubleTree by Hilton Hotel Orlando at SeaWorld
The Grove Resort & Water Park Orlando
The Grove Resort & Water Park Orlando
4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is CA $273 per night from Jun. 10 to Jun. 11
CA $273
CA $375 total
includes taxes & fees
Jun 10 - Jun 11
8.2/10 Very Good! (5,408 reviews)
"I loved the water park. The staff was so friendly and helpful. Our room was beautiful. I find it odd you have to pay for room service though!"

Reviewed on May 28, 2024

The Grove Resort & Water Park Orlando
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 $162 per night from Jun. 6 to Jun. 7
CA $162
CA $182 total
includes taxes & fees
Jun 6 - Jun 7
8.2/10 Very Good! (6,333 reviews)
"All in all the hotel was pretty nice"

Reviewed on May 30, 2024

DoubleTree by Hilton at the Entrance to Universal Orlando
See all 52,695 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

Frequently asked questions

How much does a Windermere vacation package cost?
Maybe less than you imagined — from only CA $558, as a matter of fact! By bundling flights, hotels and car rentals into a custom-made package, your getaway to Windermere is just a few clicks away.
How do I get a cheap travel package to Windermere?
Bundle your flights and hotels with Expedia to save big on your next big adventure. With over 550 partner airlines and 1,000,000 hotel options across the world, your Windermere vacation package can be tailored exactly to suit your travel style. With all that extra cash, why not include one or two exciting tours and experiences? It’s an easy way to unlock even more bargains. Your dream vacation in Windermere is much closer than you thought!
Where should I stay in Windermere?
Stay close to the action. Many visitors book hotels around popular sights, like Arnold Palmers Bay Hill Golf Club, Isleworth Golf and Country Club and Windermere Country Club.
What are the top hotels in Windermere?
Captains Lake House is one of Windermere’s best hotels. Book a room here and you can sleep soundly knowing you’re in good hands.
How far in advance should I book my Windermere vacation?
To score rock-bottom prices, book ASAP. Air carriers usually advertise flight tickets, along with some of the lowest fares, around a year prior to departure. Hotels, car rental and experiences should also be booked well in advance so you can have the pick of the bunch. If you were hoping for a last-minute getaway in Windermere, there are always lots of great deals to be had on Expedia. Book something in today!
What does an Expedia Windermere travel package include?
It depends on what kind of getaway you want to have. Windermere travel deals can include flights, car rentals and hotels. You can mix and match to create the bundle that works for you! You can also add on experiences and activities after you’ve booked to land even bigger discounts.
What should I know before booking a Windermere travel package?
You can save big by bundling your hotels, flights and rental cars. Once you’ve made your booking, you can add on tours and activities. Your next awesome vacation is only a couple of clicks away.
Can I choose my airline with a Windermere Expedia vacation package?
You can. We have more than 550 airline partners all over the world, so pick the carrier that best fits your travel preferences.
If I'm not able to travel, can I cancel my Windermere vacation package?
It is possible to cancel your Windermere booking if your travel plans have changed. Whether you’ll incur a penalty or not depends on your hotel, airline or car rental company. You may be able to change or cancel your booking for free if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.

Discover the most popular places to visit in Windermere

Image for Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(226 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
Image for Universal Studios Florida

Universal Studios Florida

4.5/5(988 reviews)

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

Universal Studios Florida
Image for Universal Orlando Resort

Universal Orlando Resort

4.5/5(399 reviews)

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

Image for Aquatica Orlando

Aquatica Orlando

CA $75
Per adult
82% of travellers recommend
Aquatica Orlando
Image for Orlando: Museum of Illusions Admission Ticket

Orlando: Museum of Illusions Admission Ticket

CA $42
Per adult
84% of travellers recommend
Orlando: Museum of Illusions Admission Ticket
Image for I-RIDE Trolley Pass

I-RIDE Trolley Pass

CA $9
Per adult
84% of travellers recommend
I-RIDE Trolley Pass
See all activities in Windermere
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.