Windermere Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Windermere Vacation

Enjoy unforgettable adventures when you book a Windermere vacation package. Whether you're a foodie, art enthusiast or just a traveler who loves experiencing new places, there's something for everyone in this interesting city. If a sightseeing tour is on the to-do list during your trip to Windermere, swing by big attractions like Lake Joseph Golf Club, Diamond In The Ruff Golf Course and The Port Carling Wall. Expedia is here to help you escape the everyday. Tailor your vacation to Windermere to suit your travel style, whatever that may be.

Discover the most popular places to visit in Windermere

Torrance Barrens Dark-Sky Preserve

Torrance Barrens Dark-Sky Preserve

3/5(1 review)

Explore the great outdoors at Torrance Barrens Dark-Sky Preserve, a lovely green space in Torrance. Wander the lakeside in this family-friendly area.

Torrance Barrens Dark-Sky Preserve
Hardy Lake Provincial Park

Hardy Lake Provincial Park

You can take time to visit Hardy Lake Provincial Park during your travels to Muskoka Lakes. Wander the lakeside in this family-friendly area.

Hardy Lake Provincial Park

Muskoka Lakes Winery

You can enjoy a tasting or tour at Muskoka Lakes Winery during your travels to Bala. Visit the spas in this romantic area, or simply enjoy its restaurants.

Muskoka Lakes Winery

Windermere Hotel Deals

Windermere House

Windermere House

3.5 out of 5
2508 Windermere Road Muskoka Lakes ON
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $149 total per night from Apr 13 to Apr 14
$149 total
Apr 13 - Apr 14
Total with taxes and fees
9/10 Wonderful! (938 reviews)
Breakfast was fantastic, staffs were amazing, our friends enjoyed hot tub and sauna. Everything was good except for the dust. As a person with dust allergy, the hallway and rooms are horrible. My sinus flared up and got sick. Also there’s no other restaurant nearby so you need to dine in the ...

Reviewed on Apr 11, 2026

Windermere House
Charming Muskoka Wilderness Cottage

Charming Muskoka Wilderness Cottage

Windermere ON
9/10 Wonderful! (2 reviews)
Loved my stay here! Great little couples get away spot. Nice and clean inside the cabin, peaceful location and close to nearby restaurants, owners are very friendly and will help with any questions you may have. Over all a great experience, highly recommend!

Reviewed on Feb 9, 2026

Get rates
Charming Muskoka Wilderness Cottage
JW Marriott The Rosseau Muskoka Resort & Spa

JW Marriott The Rosseau Muskoka Resort & Spa

4.5 out of 5
1050 Paignton House Road Muskoka Lakes ON
Fully refundableReserve now, pay when you stay
$257 nightly
The price is $291 total per night from Apr 19 to Apr 20
$291 total
Apr 19 - Apr 20
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
The best in everything, Ever.

Reviewed on Apr 5, 2026

JW Marriott The Rosseau Muskoka Resort & Spa
See all 1,030 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.

Find the Best Windermere Vacation Packages

Windermere Essential Information

Language
English
Currency
Canadian dollars
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
Hardy Lake Provincial Park, Muskoka Lakes Winery and Aspen Valley Wildlife Sanctuary

More vacations you might like

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 can grab a vacation package to this destination on Expedia. But how much your vacation to Windermere costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Windermere?
If you'd like to score a cheap Windermere vacation package, consider visiting in September, November and December. You'll generally find lower prices on accommodations and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Windermere?
Usually, a handful of days is enough to check out the main sights during your Windermere vacation. But if you'd like to have time to chill out or go on day trips, think about extending your trip.
Is it worth booking a vacation package to Windermere?
Well known for its watersports, golfing and a host of other highlights, you can be certain Windermere is a good vacation destination. Some of the most popular attractions to put on your to-do list? Check out Windermere Golf & Country Club and Windermere Marina during your Windermere vacation.
How to find the best Windermere package deals?
Finding a cheap Windermere package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Windermere package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Windermere vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Windermere vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Windermere?
If you're considering a spontaneous Windermere adventure, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land amazing deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Windermere vacation packages?
If you're like us, you love going away but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Windermere vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.