Windermere Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Algonquin Lakeside Inn

Algonquin Lakeside Inn

2.5 out of 5
Price was CA $1,197, price is now CA $1,095 per person
CA $1,095
per person
Aug 25 - Sep 1
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Muskoka (YQA)
6.6/10 (872 reviews)
Extremely disappointing experience. The place was dirty and poorly maintained, the furniture was broken, the toilet and AC did not work properly, and the amenities were in terrible condition. We also had a very upsetting privacy issue during our stay. Definitely not worth the money, and I would not recommend this place.

Reviewed on Jul 12, 2026

Miners Bay Lodge

Miners Bay Lodge

3.5 out of 5
Price was CA $1,459, price is now CA $1,216 per person
CA $1,216
per person
Aug 25 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Muskoka (YQA)
9/10 Wonderful! (16 reviews)
A beautiful cabin with all mod cons

Reviewed on Oct 20, 2025

Haliburton Post House

Haliburton Post House

4 out of 5
Price was CA $2,226, price is now CA $1,985 per person
CA $1,985
per person
Aug 25 - Sep 1
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Muskoka (YQA)
10/10 Exceptional! (2 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

Muskoka Waterfront Retreat

Muskoka Waterfront Retreat

3 out of 5
Price was CA $2,150, price is now CA $1,941 per person
CA $1,941
per person
Aug 25 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Muskoka (YQA)
8.6/10 Excellent! (101 reviews)
very peaceful and quiet place. no outside traffic. other cottages are even at quiet distance so make it very comfortable. private beach too.

Reviewed on Jun 18, 2026

White Birches Cottages

White Birches Cottages

3 out of 5
Price was CA $1,847, price is now CA $1,776 per person
CA $1,776
per person
Aug 25 - Sep 1
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Muskoka (YQA)
8.2/10 Very good! (13 reviews)
Stayed with my family for two nights. The cottage is very quiet even though the cottages are located in close proximity to each other. The check in and check out was simple and easy. There are plenty of water activities available to take part in (paddle board, canoes, and kayak). We would stay here again.

Reviewed on Oct 11, 2025

Ready to book your vacation to Windermere?

 

Choose your dates

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 14 to Jul 15
CA $395
CA $502 total
Jul 14 - Jul 15
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
"We arrived to a quick check in with staff holding open the doors for us and offering to help with our luggage. We arrived to a spotless room which was well furnished and comfortable. Dinner followed in the main dining room with a scrumptious meal including wine, salad, dessert and a unique main course. ..."

Reviewed on Jul 12, 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

Get rates
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $1,095 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.