Windermere Vacations from $698
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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.
The Latest Windermere vacation packages
Price found within the past 48 hours. Click for updated prices.
Muskoka Waterfront Retreat
$698
per person
Oct 19 - Oct 23
found 16 hours ago
Roundtrip flight included
San Antonio (SAT) to Muskoka (YQA)
8.4/10 Very Good! (120 reviews)
Great location right on Lake of Bays, perfect for paddling on the Oxtongue River or swimming and paddle boarding off the dock. The dock offered a great dark sky to see the stars on comfy Muskoka Chairs. Also really appreciated the way the property is illuminated with sensors, helping you feel safe and able to navigate the property in the evenings.
The cabin was simple, yet well stocked with everything we needed for a long weekend. The chairs, sofa and bed were all comfortable. Very clean inside. Felt the bathroom was a bit tight; however for 2 nights it wasn't an issue.
Only request is for more prompt and personalized communication when asking a question. I sent the same question a few times while on property and received a templated response that was never followed up on. In the end, it was not important; however had it been this could have been an issue.
Reviewed on Sep 10, 2026
Stay near popular Windermere attractions
Windermere Golf & Country Club
8.8/10 (29 reviews)
Enjoy a round of golf in Windermere at Windermere Golf & Country Club. Stroll along the lakeside or visit the spas in this family-friendly area.
Windermere Marina
8.4/10 (48 reviews)
Explore the waterfront in Windermere with a trip to Windermere Marina. Stroll along the lakeside in this family-friendly area, or seek out the golf courses.
Windermere Hotel Deals
Windermere House
2508 Windermere Road Muskoka Lakes ON
Fully refundableReserve now, pay when you stay
$221 nightly
$250 total
Oct 12 - Oct 13
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
"Beautiful Hotel, very clean & the food is very good. Staff is very helpful & they treat you with class."
Reviewed on Sep 11, 2026
Muskoka Tiny Home
Windermere ON
9.8/10 Exceptional! (11 reviews)
"We were there for a short period of time, but enjoyed every minute of it. The home is pet friendly, and the area is quite unique. There are also many place near by such as: waterfalls, strawberry farm, and convinces store. Nice place to go to get away from the city and unwind."
Reviewed on Sep 2, 2026
3 Mile Lakehouse
Utterson ON
$454 nightly
$513 total
Sep 13 - Sep 14
Total with taxes and fees
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 |
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Frequently asked questions
How much does a Windermere vacation package cost?
You can grab a vacation package to this destination from $698 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.
