Windermere Vacations from $667

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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.
Blue Mountain Resort Village Suites

Blue Mountain Resort Village Suites

4 out of 5
Price was $774, price is now $667 per person
$667
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Muskoka (YQA)
8.8/10 Excellent! (4,539 reviews)
Love the location right in the village and the underground parking was great Lovely staff, easy check in The suite had everything needed, they though of everything Lots of room

Reviewed on Dec 10, 2025

Blue Mountain Resort Mosaic Suites

Blue Mountain Resort Mosaic Suites

2.5 out of 5
Price was $815, price is now $695 per person
$695
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Muskoka (YQA)
8.8/10 Excellent! (1,382 reviews)
Amazing and clean room and the staff are very friendly the place is very beautiful

Reviewed on Nov 11, 2025

Hilton Grand Vacations Club Blue Mountain Canada

Hilton Grand Vacations Club Blue Mountain Canada

3 out of 5
Price was $739, price is now $696 per person
$696
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Muskoka (YQA)
9.2/10 Wonderful! (1,000 reviews)
Staff was great to deal with. Video game room was fun. Perfect location to enjoy Blue Mountain.

Reviewed on Dec 8, 2025

Arlberg Chalets

Arlberg Chalets

3 out of 5
Price was $2,666, price is now $2,518 per person
$2,518
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Muskoka (YQA)
9.4/10 Exceptional! (3 reviews)
Spacious chalet for family celebration. Minor issues when we checked in and the service of the staff was prompt and friendly. Bathrooms are only on the main level which proved to be a little inconvenient for children in the middle of the night. Other than that we enjoyed our stay!!

Reviewed on Aug 14, 2025

Birch View Chalets

Birch View Chalets

3 out of 5
Price was $1,702, price is now $1,619 per person
$1,619
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Muskoka (YQA)
No reviews
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Discover the most popular places to visit in Windermere

Look close to find the cranberries in the bushes.

Muskoka Lakes Winery

You can enjoy a tasting or tour at Muskoka Lakes Winery during your travels to Bala. Visit the spas in this romantic area, or simply enjoy its restaurants.

Muskoka Lakes Winery
Lake Muskoka Chair...spotted some of these nice chairs all around, and this one provided a very relaxing stop while hiking the parameter of a small part of this huge lovely lake. #greatoutdoors

Hardy Lake Provincial Park

You can take time to visit Hardy Lake Provincial Park during your travels to Muskoka Lakes. Wander the lakeside in this family-friendly area.

Hardy Lake Provincial Park

Torrance Barrens Dark-Sky Preserve

3/5(1 review)

Explore the great outdoors at Torrance Barrens Dark-Sky Preserve, a lovely green space in Torrance. Wander the lakeside in this relaxing area.

Torrance Barrens Dark-Sky Preserve

Windermere Hotel Deals

Windermere House

Windermere House

3.5 out of 5
2508 Windermere Road Muskoka Lakes ON
$132 nightly
The price is $149 total per night from Dec 16 to Dec 17
$149 total
Dec 16 - Dec 17
Total with taxes and fees
9/10 Wonderful! (867 reviews)
Great breakfast buffet style. The property is a hidden gem. We went off season in November for a quick reset and relax. The sauna barrels are lovely has lake view. And the hottub is popular during the night. They have the pool open for cold plunges as well. Friendly staff and rooms were clean. Bathrobes ...

Reviewed on Dec 3, 2025

Windermere House
Cozy Muskoka Winter Escape **Hot Tub** **Hidden Valley Ski Resort**

Cozy Muskoka Winter Escape **Hot Tub** **Hidden Valley Ski Resort**

Utterson ON
9.6/10 Exceptional! (20 reviews)
Had a lovely short stay; hot tub was a highlight.

Reviewed on Oct 20, 2025

Get rates
Cozy Muskoka Winter Escape **Hot Tub** **Hidden Valley Ski Resort**
3 Mile Lakehouse

3 Mile Lakehouse

Utterson ON
$454 nightly
The price is $513 total per night from Dec 13 to Dec 14
$513 total
Dec 13 - Dec 14
Total with taxes and fees
6.6/10 (4 reviews)
the place is so neat and cleanstunning and gorgeous view.. we enjoy the weekend stay.

Reviewed on Oct 5, 2025

3 Mile Lakehouse
See all 945 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 $667 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.