Windermere Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Find the Best Windermere Vacation Packages

Windermere Hotel Deals

Windermere House

Windermere House

3.5 out of 5
2508 Windermere Road, Muskoka Lakes, ON
The price is ￥42,950 per night from Jul 27 to Jul 28
￥42,950
￥54,494 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (756 reviews)
"For a luxury resort the prices and the overall experience didn’t match up to international standards in our experience. The buffet was average and the rules that the staff have to follow are definitely not very gracious….NB more for special coffee or special drinks and they make sure the guests know ..."

Reviewed on Jul 21, 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
8/10 Very Good! (1 review)
Muskoka Lake Stay
"Great lake! The boat house was clean and cozy, well equipped. The only thing is that it needs more lighting. The drive way slopes so stay on the gravel part as the car can get stuck if parked on the steep non gravel part especially if the ground is wet it can be muddy. The driveway that leads to ..."

Reviewed on Jul 3, 2024

Get rates
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
The price is ￥60,281 per night from Aug 10 to Aug 11
￥60,281
￥85,018 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Excellent property, staff was friendly, food was incredible. We have older children there was plenty to do."

Reviewed on Jul 22, 2025

JW Marriott The Rosseau Muskoka Resort & Spa
See all 1,015 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.

Frequently asked questions

How much does a Windermere vacation package cost?
You can grab a vacation package to this destination on Expedia. But how much your vacation to Windermere costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Windermere?
Plan your trip for the off-peak season and you're likely to score cheap Windermere vacation packages. Bear in mind that public holidays and local events and festivals can have an impact on prices, so do your research before booking.
How many days is enough for Windermere?
The ideal duration of your Windermere vacation depends on what you'd like to see. Generally, a handful of days to a week will give you enough time to check out all the leading attractions and explore some hidden gems along the way.
How to find the best Windermere package deals?
Finding a cheap Windermere package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Windermere package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically 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 flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Windermere vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Windermere?
If you're considering a spontaneous Windermere adventure, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Windermere?

  1. Pick your travel dates: The things you plan to do in Windermere and your favorite season can help you decide when to get away.
  2. Plan your budget wisely: In addition to the cost of your accommodations, you should factor in other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected costs that could arise during your trip to Windermere.
  3. Work out your trip length: Consider how much time you'd like to spend exploring Windermere. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose 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.