Windermere Vacations from $324
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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.
Haliburton Post House
$545
per person
Sep 8 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Muskoka (YQA)
10/10 Exceptional! (3 reviews)
We were unfamiliar with the Haliburton Post House and booked two nights , mid week, on a whim to get out of town. The room was beautiful, the food and wine selection was great. We took advantage of their waterfront and toys on what may have been the hottest day of the year. Thanks to the staff who made us feel welcome and were the highlight of our stay.
Reviewed on Jul 3, 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 relaxing area, or seek out the golf courses.
What to do in Windermere
Private 4 Day Algonquin Park Backcountry Canoe Trip
$1,062
per adult
Windermere Hotel Deals
Windermere House
2508 Windermere Road Muskoka Lakes ON
Fully refundableReserve now, pay when you stay
$277 nightly
$313 total
Sep 7 - Sep 8
Total with taxes and fees
Muskoka Tiny Home
Windermere ON
9.8/10 Exceptional! (6 reviews)
"My girlfriend and I spent a great weekend in this home. It had everything you need and was clean and comfy."
Reviewed on Aug 4, 2026
Charming Muskoka Wilderness Cottage
Windermere ON
9.6/10 Exceptional! (10 reviews)
"What can i say about this super amazing property??? The home will make you feel like you are waking up in your own home. Beautiful cabin, everything you need and then some. The pond is nothing short of amazing to sit and have a fire by and watch the nightlife come out to play.. Cannot wait to return ..."
Reviewed on Jul 29, 2026
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 $324 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.
