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.

Top Windermere Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sunnylea Resort

Sunnylea Resort

2.5 out of 5
Price was CA $1,240, price is now CA $1,022 per person
CA $1,022
per person
Aug 26 - Aug 31
found 2 hours ago
Roundtrip flight included
Saskatoon (YXE) to Muskoka (YQA)
8.4/10 Very good! (90 reviews)
We loved the pool and the easy access to the water toys like kayaks and paddle boards. They supplied the life jackets which was helpful and supplied all the linens, towels and even provided soap and shampoo. It is a beautiful firepit and nice sandy volleyball pit. There isn’t swimming off the dock, as the water is full of reeds but the water is clean and lots of opportunities to go out into deeper water to swim. We loved it!

Reviewed on Jul 7, 2026

Rocky Crest Golf Resort

Rocky Crest Golf Resort

4 out of 5
Price was CA $1,636, price is now CA $1,322 per person
CA $1,322
per person
Aug 26 - Aug 31
found 2 hours ago
Roundtrip flight included
Saskatoon (YXE) to Muskoka (YQA)
8.2/10 Very good! (402 reviews)
Incredible experience.. super great time!

Reviewed on Jul 7, 2026

The Dudley Inn

The Dudley Inn

2.5 out of 5
Price was CA $1,704, price is now CA $1,491 per person
CA $1,491
per person
Aug 26 - Aug 31
found 2 hours ago
Roundtrip flight included
Saskatoon (YXE) to Muskoka (YQA)
9.8/10 Exceptional! (75 reviews)
This was a wonderful place to stay. Lovely spacious room in a great location. Would most definitely recommend it.

Reviewed on Jul 11, 2026

Port Cunnington Lodge

Port Cunnington Lodge

3.5 out of 5
Price was CA $1,484, price is now CA $1,305 per person
CA $1,305
per person
Aug 26 - Aug 31
found 2 hours ago
Roundtrip flight included
Saskatoon (YXE) to Muskoka (YQA)
9.6/10 Exceptional! (31 reviews)
The site listed that there is onsite restaurant for breakfast, dinner and snacks . They site also lists that this is unique find because this property offers continental breakfast. None of that is true . The dinner at restaurant- reservation closes at 2pm and it’s an expensive buffet . No breakfast. They had croissants available for pick and go in a paper bag. Not even a comfy place to sit and peacefully eat. Nearest food place is in Huntsville which is 30 mins drive . Such a ridiculous false advertisement for a $450 night property . Such a shame that they advertise but don’t provide continental breakfast

Reviewed on Jul 5, 2026

The Bala Bay Inn

The Bala Bay Inn

2 out of 5
Price was CA $1,224, price is now CA $1,089 per person
CA $1,089
per person
Aug 26 - Aug 31
found 2 hours ago
Roundtrip flight included
Saskatoon (YXE) to Muskoka (YQA)
6.8/10 (12 reviews)
The beer spa was a genius addition

Reviewed on Jul 7, 2026

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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 CA $395 per night from Jul 13 to Jul 14
CA $395
CA $502 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
"Very relaxing and beautiful rooms: the Seguin Suite wonderful!"

Reviewed on Jul 11, 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 Jul 8, 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 Jun 14, 2026

Get rates
Charming Muskoka Wilderness Cottage
See all 1,050 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.
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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.
See properties

Frequently asked questions

How much does a Windermere vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,022 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.

Explore a world of travel with Expedia

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