Windermere Vacations from $581

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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.

The Latest Windermere vacation packages

Price found within the past 48 hours. Click for updated prices.
Algonquin Lakeside Inn

Algonquin Lakeside Inn

2.5 out of 5
Price was $641, price is now $581 per person
$581
per person
Aug 27 - Aug 31
found 23 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Muskoka (YQA)
6.6/10 (872 reviews)
Non responsive to communication

Reviewed on Jul 14, 2026

The Dudley Inn

The Dudley Inn

2.5 out of 5
Price was $1,183, price is now $1,001 per person
$1,001
per person
Aug 27 - Aug 31
found 23 hours ago
Roundtrip non-stop flight included
Austin (AUS) 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

Rocky Crest Golf Resort

Rocky Crest Golf Resort

4 out of 5
Price was $1,016, price is now $869 per person
$869
per person
Aug 27 - Aug 31
found 23 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Muskoka (YQA)
8.2/10 Very Good! (402 reviews)
Incredible experience.. super great time!

Reviewed on Jul 7, 2026

Muskoka Waterfront Retreat

Muskoka Waterfront Retreat

3 out of 5
Price was $1,148, price is now $985 per person
$985
per person
Aug 27 - Aug 31
found 23 hours ago
Roundtrip non-stop flight included
Austin (AUS) 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

Touchstone Resort

Touchstone Resort

4 out of 5
Price was $1,402, price is now $1,276 per person
$1,276
per person
Aug 27 - Aug 31
found 23 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Muskoka (YQA)
8.6/10 Excellent! (417 reviews)

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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.
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What to do in Windermere

Private 4 Day Algonquin Park Backcountry Canoe Trip

Private 4 Day Algonquin Park Backcountry Canoe Trip

$1,057
per adult
Private 4 Day Algonquin Park Backcountry Canoe Trip
See all activities in Windermere

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
$291 nightly
The price is $328 total per night from Jul 26 to Jul 27
$328 total
Jul 26 - Jul 27
Total with taxes and fees
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 1,049 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.

Find the Best Windermere Vacation Packages

Windermere Essential Information

Language
English
Currency
Canadian dollars
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
Hardy Lake Provincial Park, Muskoka Lakes Winery and Aspen Valley Wildlife Sanctuary

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Frequently asked questions

How much does a Windermere vacation package cost?
You can grab a vacation package to this destination from $581 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?
If you'd like to score a cheap Windermere vacation package, consider visiting in September, November and December. You'll generally find lower prices on accommodations and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Windermere?
Usually, a handful of days is enough to check out the main sights during your Windermere vacation. But if you'd like to have time to chill out or go on day trips, think about extending your trip.
Is it worth booking a vacation package to Windermere?
Well known for its watersports, golfing and a host of other highlights, you can be certain Windermere is a good vacation destination. Some of the most popular attractions to put on your to-do list? Check out Windermere Golf & Country Club and Windermere Marina during your Windermere vacation.
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.
Does Expedia offer Book Now, Pay Later Windermere vacation packages?
If you're like us, you love going away but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Windermere vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.