Windermere Holidays

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Windermere Holiday

Our pick of the best Windermere Hotel Deals

Windermere House

Windermere House

2508 Windermere Road Muskoka Lakes ON
Fully refundableReserve now, pay when you stay
NZ$530
7 Sept - 8 Sept
includes taxes & fees
Windermere House
Muskoka Tiny Home

Muskoka Tiny Home

Windermere ON
9.8/10 Exceptional! (6 reviews)
"My girlfriend and I spent a great weekend in this home. It had everything you need and was clean and comfy."

Reviewed on 4 Aug 2026

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Muskoka Tiny Home
Charming Muskoka Wilderness Cottage

Charming Muskoka Wilderness Cottage

Windermere ON
9.6/10 Exceptional! (10 reviews)
"What can i say about this super amazing property??? The home will make you feel like you are waking up in your own home. Beautiful cabin, everything you need and then some. The pond is nothing short of amazing to sit and have a fire by and watch the nightlife come out to play.. Cannot wait to return ..."

Reviewed on 29 July 2026

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Charming Muskoka Wilderness Cottage
See all 866 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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Windermere Marina

8.4/10 (48 reviews)
Explore the waterfront in Windermere with a trip to Windermere Marina. Stroll along the lakeside in this relaxing area or seek out the golf courses.
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Frequently asked questions

How much does a Windermere holiday package cost?
You can grab a holiday package to this destination on Expedia. But how much your holiday 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 holiday 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 holiday 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 personalise your search by "Amenities," "Property type," "Traveller 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 holiday as a package?
Expedia holiday 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 personalised Windermere holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday 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 favourite season can help you decide when to get away.
  2. Plan your budget wisely: In addition to the cost of your accommodation, 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 holiday package that brings all your bookings together.

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