Windermere Vacations

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Find the Best Windermere Vacation Packages

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
The price is AEDĀ 822 per night from Jul 26 to Jul 27
AEDĀ 822
AEDĀ 1,073 total
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"One of a few beautiful iconic historic resorts left in Ontario. Only 58 rooms and personal touches ... not a huge hotel. Excellent dinner and location. Large pool and great selection of free activities like shuffle board and volley ball. Minor point ... shower curtain needs to be washed to remove ..."

Reviewed on 16 July 2026

Windermere House
Muskoka Tiny Home

Muskoka Tiny Home

Windermere ON
9.6/10 Exceptional! (5 reviews)
"We absolutely loved our stay in the Muskoka Tiny House. It had everything we needed to cook some delicious meals on our anniversary getaway, was very clean and the host was quick to respond to any inquiries we had. There are two barbeques on the property as well as a small firepit for roasting marshmallows. ..."

Reviewed on 8 July 2026

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Muskoka Tiny Home
Charming Muskoka Wilderness Cottage

Charming Muskoka Wilderness Cottage

Windermere ON
9.8/10 Exceptional! (7 reviews)
"The cottage was modern and clean as advertised. It has everything you need in kitchen to cook meals or BBQ on deck. It is able to accommodate a family of 4 with extra bedroom. Communication was good with host ."

Reviewed on 14 June 2026

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Charming Muskoka Wilderness Cottage
See all 1,049 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.

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.
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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 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, favorite 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.