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.
Bobcaygeon Resort

Bobcaygeon Resort

3.5 out of 5
Price was CA $799, price is now CA $570 per person
CA $570
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Muskoka (YQA)
8.8/10 Excellent! (35 reviews)
Excellent.location and property. Water is clean with lots of options to boat, swim or just relax at the water front. Highly recommend.

Reviewed on Aug. 17, 2025

Lakefront Hideaway Resort

Lakefront Hideaway Resort

3 out of 5
Price was CA $1,197, price is now CA $821 per person
CA $821
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Muskoka (YQA)
No reviews
Modern Designed Home

Modern Designed Home

2 out of 5
Price was CA $26,661, price is now CA $21,057 per person
CA $21,057
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Muskoka (YQA)
No reviews
Hilton Grand Vacations Club Blue Mountain Canada

Hilton Grand Vacations Club Blue Mountain Canada

3 out of 5
Price was CA $1,900, price is now CA $1,560 per person
CA $1,560
per person
Oct 9 - Oct 13
found 20 hours ago
Roundtrip flight included
Sudbury (YSB) to Muskoka (YQA)
9.2/10 Wonderful! (1,004 reviews)
Great property! Will. Be visiting again next year!

Reviewed on Sep. 2, 2025

The Saucy Willow Inn and Cottages

The Saucy Willow Inn and Cottages

4 out of 5
Price was CA $1,084, price is now CA $902 per person
CA $902
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Muskoka (YQA)
10/10 Exceptional! (82 reviews)
From the time you check in to your entire stay you feel very welcome. It is such a special property and a must see. Stephanie and Dave have done a wonderful job, enjoyed every minute.

Reviewed on Aug. 27, 2025

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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 $299 per night from Sep 7 to Sep 8
CA $299
CA $393 total
Sep 7 - Sep 8
includes taxes & fees
Windermere House
JW Marriott The Rosseau Muskoka Resort & Spa

JW Marriott The Rosseau Muskoka Resort & Spa

4.5 out of 5
1050 Paignton House Road, Muskoka Lakes, ON
Fully refundableReserve now, pay when you stay
The price is CA $365 per night from Sep 28 to Sep 29
CA $365
CA $508 total
Sep 28 - Sep 29
includes taxes & fees
JW Marriott The Rosseau Muskoka Resort & Spa
Residence Inn by Marriott Gravenhurst Muskoka Wharf

Residence Inn by Marriott Gravenhurst Muskoka Wharf

3 out of 5
285 Steamship Bay Road, Gravenhurst, ON
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from Sep 21 to Sep 22
CA $220
CA $259 total
Sep 21 - Sep 22
includes taxes & fees
Residence Inn by Marriott Gravenhurst Muskoka Wharf
See all 976 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
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Family Vacations

Discover the most popular places to visit in Windermere

Muskoka Lakes Winery

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 family-friendly area, or simply enjoy its restaurants.

Muskoka Lakes Winery
Hardy Lake Provincial Park

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

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 relaxing area.

Torrance Barrens Dark-Sky Preserve
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.