Windermere Vacation Packages

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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.

Top Windermere Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Lakefront Hideaway Resort

Lakefront Hideaway Resort

3 out of 5
Price was CA $1,557, price is now CA $1,187 per person
CA $1,187
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
St. John's (YYT) to Muskoka (YQA)
No reviews
Haliburton Post House

Haliburton Post House

4 out of 5
Price was CA $1,602, price is now CA $1,410 per person
CA $1,410
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
St. John's (YYT) to Muskoka (YQA)
No reviews

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Windermere Hotel Deals

Windermere House

Windermere House

3.5 out of 5
2508 Windermere Road Muskoka Lakes ON
The price is CA $134 per night from Feb 20 to Feb 21
CA $134
CA $207 total
Feb 20 - Feb 21
includes taxes & fees
9/10 Wonderful! (899 reviews)
Nice place and a great price, we will Be going again!

Reviewed on Jan 9, 2026

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

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

Muskoka Tiny Home

Windermere ON
10/10 Exceptional! (1 review)
Great location!

Reviewed on Jan 25, 2026

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Muskoka Tiny Home
See all 1,005 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.
All Inclusive Vacations
All Inclusive Vacations
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Family Vacations

Discover the most popular places to visit in Windermere

One of my favourite spots to explore, the Torrance Barrens Dark-Sky Preserve is a little spot in Ontario Cottage Country that is free from any near-by light pollution which makes for some impressive night skies. #BvSApplication

Torrance Barrens Dark-Sky Preserve

4/5(23 reviews)

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

Torrance Barrens Dark-Sky Preserve
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

5/5(5 reviews)

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

Muskoka Lakes Winery

4.5/5(31 reviews)

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

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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.