Windermere Vacations from $851

Book a Hotel + Flight or Car together to unlock savings

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.
Tay Motel

Tay Motel

2.5 out of 5
Price was $864, price is now $851 per person
$851
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Miami (MIA) to Muskoka (YQA)
8.4/10 Very Good! (71 reviews)

The Dudley Inn

The Dudley Inn

2.5 out of 5
Price was $1,167, price is now $1,081 per person
$1,081
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Miami (MIA) to Muskoka (YQA)
9.8/10 Exceptional! (112 reviews)
Check in was easy and the staff was great. Well maintained and updated property in a great location! Highly recommend

Reviewed on Oct 25, 2026

Windermere House

Windermere House

3.5 out of 5
Price was $1,190, price is now $1,105 per person
$1,105
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Miami (MIA) to Muskoka (YQA)
9.2/10 Wonderful! (1,017 reviews)
none

Reviewed on Oct 28, 2026

Sherwood Inn

Sherwood Inn

4 out of 5
Price was $891, price is now $869 per person
$869
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Miami (MIA) to Muskoka (YQA)
8.8/10 Excellent! (936 reviews)
First stayed in 1990 and it was so nice to return. The grounds, accommodations, restaurants and above all the kind, welcoming professional staff. The meals are exceptional. Beautiful views and many places to sit by the lake or take a stroll on the trails. Many games including tennis, pickle ball, kayaks, canoes, shuffle board, corn hole, ladder golf etc. A very relaxing and serene atmosphere. Ten minutes to Port Carling and Bala; 40 minutes to Gravenhurst. Can't wait to return and it won't be another 36 years this time! Lol

Reviewed on Oct 28, 2026

Christie's Mill Inn & Spa

Christie's Mill Inn & Spa

3.5 out of 5
Price was $938, price is now $917 per person
$917
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Muskoka (YQA)
8/10 Very Good! (436 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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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
$134 nightly
The price is $151 total per night from Oct 30 to Oct 31
$151 total
Oct 30 - Oct 31
Total with taxes and fees
9.2/10 Wonderful! (1,005 reviews)
"none"

Reviewed on Oct 28, 2026

Windermere House
Muskoka Tiny Home

Muskoka Tiny Home

Windermere ON
9.8/10 Exceptional! (19 reviews)
"We had a wonderful stay! The place was lovely and peaceful. Fall is especially beautiful in this area, and we really enjoyed the atmosphere, local shops, and events. We’d happily come back again!"

Reviewed on Oct 18, 2026

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Muskoka Tiny Home
Charming Muskoka Wilderness Cottage

Charming Muskoka Wilderness Cottage

Windermere ON
9.2/10 Wonderful! (19 reviews)
"Very peaceful property. Easy to locate. Very affordable and clean. Great for couples or small families."

Reviewed on Oct 17, 2026

Get rates
Charming Muskoka Wilderness Cottage
See all 1,025 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 $851 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.