Windermere Vacation Packages

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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.

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Windermere Hotel Deals

Windermere House

Windermere House

3.5 out of 5
2508 Windermere Road, Muskoka Lakes, ON
The price is CA $269 per night from Sep 7 to Sep 8
CA $269
CA $359 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (793 reviews)
"Breakfast choices are great. Beds are comfortable."

Reviewed on Aug. 15, 2025

Windermere House
Lake Rosseau Muskoka Cottage Rental 5 min from Windermere w boat/trailer parking

Lake Rosseau Muskoka Cottage Rental 5 min from Windermere w boat/trailer parking

utterson windermere muskoka
9/10 Wonderful! (2 reviews)
"Loved this rustic boat house cottage in a quiet bay of Lake Rosseau - shallow water, great for swimming, can catch fish off the dock and comfy beds. Owner is very responsive and friendly - with lots of local knowledge."

Reviewed on Jul. 26, 2025

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Lake Rosseau Muskoka Cottage Rental 5 min from Windermere w boat/trailer parking
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
The price is CA $424 per night from Sep 14 to Sep 15
CA $424
CA $579 total
Sep 14 - Sep 15
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"The food was outstanding the drinks very unique and flavourful great service and great customer service overall you won’t be disappointed eating at this place or the drink menu"

Reviewed on Aug. 16, 2025

JW Marriott The Rosseau Muskoka Resort & Spa
See all 977 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

Muskoka Lakes Winery

Muskoka Lakes Winery

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

Muskoka Lakes Winery
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

Torrance Barrens Dark-Sky Preserve

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

Torrance Barrens Dark-Sky Preserve

Frequently asked questions

How much does a Windermere vacation package cost?
You can snap up a vacation package to this popular destination on Expedia. However, how much your vacation to Windermere costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Windermere?
To score cheap Windermere vacation packages, organize your trip outside of peak periods such as school holidays. You'll typically find better availability and lower prices for hotels and flights.
How many days is enough for Windermere?
With a well-planned itinerary, you can easily visit the most popular Windermere sights in a handful of days. But if you'd like to discover hidden gems or go on day trips, think about booking your Windermere vacation for longer.
How to find the best Windermere package deals?
Bagging a cheap Windermere package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, add a few filters and see what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Windermere package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often 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 hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Windermere vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Windermere?
Enjoy fantastic discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Windermere trip.
How to plan a trip to Windermere?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to Windermere.
  2. Set your budget: Consider expenses such as transportation, flights and meals when calculating how much to set aside for your trip to Windermere. Then, select a property that works with your budget, whether that's a wallet-friendly stay or a more luxurious retreat.
  3. Decide how long to go away for: Now that you know more about Windermere, you can figure out the right length of your vacation. Put together a rough itinerary and give yourself enough time to cover everything you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to find a Windermere vacation package that brings all your bookings together.

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