Windermere Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Jolly Roger Inn & Resort

Jolly Roger Inn & Resort

3.5 out of 5
Price was CA $794, price is now CA $737 per person
CA $737
per person
Jun 18 - Jun 22
found 4 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Muskoka (YQA)
7.8/10 Good! (643 reviews)
Room was great!!! Staff were nice!!! It would of been nice if the hot tub was working…

Reviewed on Mar 6, 2026

Muskoka Waterfront Retreat

Muskoka Waterfront Retreat

3 out of 5
Price was CA $1,281, price is now CA $1,131 per person
CA $1,131
per person
Jun 18 - Jun 22
found 4 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Muskoka (YQA)
8.6/10 Excellent! (75 reviews)
Beautiful..homey... place to stay..recommend

Reviewed on Mar 14, 2026

Tally-Ho Inn

Tally-Ho Inn

2.5 out of 5
Price was CA $891, price is now CA $821 per person
CA $821
per person
Jun 18 - Jun 22
found 4 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Muskoka (YQA)
8.6/10 Excellent! (940 reviews)
Love this place. We’ll be back next march

Reviewed on Mar 16, 2026

The Bala Bay Inn

The Bala Bay Inn

2 out of 5
Price was CA $980, price is now CA $926 per person
CA $926
per person
Jun 18 - Jun 22
found 24 hours ago
Roundtrip flight included
Winnipeg (YWG) to Muskoka (YQA)
6.6/10 (9 reviews)
We had a great one night stay - in Bala for a concert at The Kee. Rooms are not generally air conditioned but we lucked out with one. Clean and well taken care of. Would definitely stay again but would insist on an air conditioner!

Reviewed on Jul 7, 2025

Ready to book your vacation to Windermere?

 

Choose your dates

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
The price is CA $149 per night from Mar 29 to Mar 30
CA $149
CA $224 total
Mar 29 - Mar 30
includes taxes & fees
9/10 Wonderful! (924 reviews)
The property is beautiful, very clean, and thoughtfully updated. There were considerate touchea throughout the experience, the food was excellent, and the amenities were superb.

Reviewed on Mar 23, 2026

Windermere House
Charming Muskoka Wilderness Cottage

Charming Muskoka Wilderness Cottage

Windermere ON
9/10 Wonderful! (2 reviews)
Loved my stay here! Great little couples get away spot. Nice and clean inside the cabin, peaceful location and close to nearby restaurants, owners are very friendly and will help with any questions you may have. Over all a great experience, highly recommend!

Reviewed on Feb 9, 2026

Get rates
Charming Muskoka Wilderness Cottage
3 Mile Lakehouse

3 Mile Lakehouse

Utterson ON
The price is CA $400 per night from Mar 26 to Mar 27
CA $400
CA $707 total
Mar 26 - Mar 27
includes taxes & 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 1,003 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
Beach Vacations
Beach Vacations
Family Vacations
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 relaxing 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 family-friendly area, or simply enjoy its restaurants.

Muskoka Lakes Winery

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.