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.
Muskoka Waterfront Retreat

Muskoka Waterfront Retreat

CA $618
per person
Nov 20 - Nov 23
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Muskoka (YQA)
8.4/10 Very good! (139 reviews)
Very good

Reviewed on Oct 12, 2026

Windermere House

Windermere House

CA $974
per person
Nov 20 - Nov 23
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Muskoka (YQA)
9.2/10 Wonderful! (1,009 reviews)
Lovely resort located on beautiful Lake Rousseau. The lakeside view from the hotel is spectacular especially in the fall. The room was clean, spacious and lead to a balcony overlooking the lake. Breakfast (included with your stay) offered both hot and cold items in a spacious buffet dining room. I would definitely recommend staying at Windermere House.

Reviewed on Oct 14, 2026

Sandy Lane Resort

Sandy Lane Resort

CA $920
per person
Nov 20 - Nov 23
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Muskoka (YQA)
No reviews
Touchstone Resort

Touchstone Resort

CA $1,207
per person
Nov 20 - Nov 23
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Muskoka (YQA)
8.6/10 Excellent! (457 reviews)
Clean room, excellent service and facilities

Reviewed on Oct 14, 2026

Modern Muskoka Cottage with Lake Views

Modern Muskoka Cottage with Lake Views

CA $1,300
per person
Nov 20 - Nov 23
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Muskoka (YQA)
No reviews

Ready to book your vacation to Windermere?

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Windermere Hotel Deals

Windermere House

Windermere House

2508 Windermere Road Muskoka Lakes ON
Fully refundableReserve now, pay when you stay
CA $173
CA $251 total
Nov 8 - Nov 9
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Lovely resort located on beautiful Lake Rousseau. The lakeside view from the hotel is spectacular especially in the fall. The room was clean, spacious and lead to a balcony overlooking the lake. Breakfast (included with your stay) offered both hot and cold items in a spacious buffet dining room. ..."

Reviewed on Oct 14, 2026

Windermere House
Muskoka Tiny Home

Muskoka Tiny Home

Windermere ON
9.8/10 Exceptional! (15 reviews)
"Overall experience was great. Few little things that I would like to pin point was window coverings. The bedroom has no window coverings and so as the living room window. Rest was a great experience and the cabin was uniquely comfortable and clean. ⭐️ ⭐️ ⭐️ ⭐️ ⭐️"

Reviewed on Sep 30, 2026

Get rates
Muskoka Tiny Home
3 Mile Lakehouse

3 Mile Lakehouse

Utterson ON
CA $400
CA $711 total
Oct 18 - Oct 19
includes taxes & fees
5.8/10 (9 reviews)
"Just don't. Find something else."

Reviewed on Sep 29, 2026

3 Mile Lakehouse
See all 1,021 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
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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

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.
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 $618 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.