Windermere Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Windermere

Touchstone Resort
4.0 star property
8.6 out of 10, Excellent, (231)
"Front desk was amazing to deal with and very welcoming. Will definitely be back."
The price is CA $189
CA $229 total
includes taxes & fees
Jun 4 - Jun 5
Touchstone Resort
Muskoka Lake Cottages
3.0 star property
7.2 out of 10, Good, (36)
"The cottage was cozy and the view was beautiful!"
The price is CA $134
CA $208 total
includes taxes & fees
Jun 2 - Jun 3
Muskoka Lake Cottages
Renovated Waterfront Cottage on Three Mile Lake in the heart of Muskoka.
9.4 out of 10, Exceptional, (13)
"Wonderful vac..beautiful view and the cottage was perfect for us!"
Renovated Waterfront Cottage on Three Mile Lake in the heart of Muskoka.
Save an average of 15% on thousands of hotels when you're signed in
Welcome to Falcon’s Nest, your 6 bedroom luxury all-season cottage retreat nestled on Lake Muskoka
10.0 out of 10, Exceptional, (22)
"Our family had such a special time together at the Falcon's Nest. The house was immaculate, there were special touches across the home, lovely soaps, chocolates, and the most incredible charcuterie board we've ever seen! Preet was so attentive to all of our needs, and we couldn't have asked for a better visit. Thank you!"
Welcome to Falcon’s Nest, your 6 bedroom luxury all-season cottage retreat nestled on Lake Muskoka
260 feet of South West lakefront on Lake Joseph with all day sun
8.8 out of 10, Excellent, (3)
"My husband and I and another couple had a great holiday in the Muskokas. Our host, Loren was easy to communicate with and very helpful. The cottage was spacious, clean and well equipped. The bedrooms were very comfortable. We especially liked the boat dock with bunky across the road from the cottage. We had easy access to all three of lakes. Port Carling and Port Sandfield was close with lots of amenities. The pictures are accurate of what the cottage looks like. We would rent this place again...
260 feet of South West lakefront on Lake Joseph with all day sun
Log Cabin On the Lake B&B
10.0 out of 10, Exceptional, (7)
"Spent my girlfriend’s birthday weekend at the cabin and had the nicest time. Perfect for a quite relaxing weekend with a perfect fire pit area and cozy inside for movie nights"
The price is CA $225
CA $385 total
includes taxes & fees
Jun 2 - Jun 3
Log Cabin On the Lake B&B
Brand new cottage on 3-Mile Lake in the heart of Muskoka
9.8 out of 10, Exceptional, (81)
"The property looks just like it does in the photos -- clean, bright, and incredibly spacious! My friends and I had such a wonderful experience, and we got so many questions from other friends asking about where we stayed. I would highly recommend this cottage to anyone looking for a stay in Muskoka!"
Brand new cottage on 3-Mile Lake in the heart of Muskoka
Cozy Cabin Overlooking Arrowhead Provincial Park and the Big East River
9.8 out of 10, Exceptional, (19)
"We loved the peacefulness of the river being right there. I loved that downtown was so close. But it felt like being faraway. Only problem with our age was all the stairs. Our one pet had to be carried up. Which was hard to do. Other then that awesome stay. Loved it"
Cozy Cabin Overlooking Arrowhead Provincial Park and the Big East River
Lakefront Muskoka Beautiful Cottage
9.0 out of 10, Wonderful, (9)
"We had a great experience. The host was very nice and accommodating. Only thing for people to remember is bring cutlery and plates and cups."
The price is CA $309
CA $484 total
includes taxes & fees
Jun 1 - Jun 2
Lakefront Muskoka Beautiful Cottage
Cozy Cottage in Muskoka
7.6 out of 10, Good, (5)
"We loved staying at the little cottage! Perfect for 2 adults, 2 kids and a dog. The fenced in yard was amazing for security of our dog as the road is very busy. The listing should say it provides a clothes drying rack, not a clothes dryer as we expected access to an electric one. With 2 girls attending wake surf camp 5 days straight it was challenging to get the towels dry. Excellent location close to all 3 lakes and shopping."
The price is CA $199
CA $410 total
includes taxes & fees
Jun 2 - Jun 3
Cozy Cottage in Muskoka
Cozy Waterfront Cottage on Muskoka River
9.0 out of 10, Wonderful, (4)
"We were very happy with the place. Peaceful, nice, and close to everything. Well supplied kitchen, good barbecue, and way more beds than we needed. Place has a basketball hoop, a volleyball court, and enough green space to place soccer with a small group of people. The river is good for swimming, shallow in the shore but deep as you jump from the dock. Everything was clean and in working order. Thanks to the owners for allowing us to stay at this place."
Cozy Waterfront Cottage on Muskoka River
Great Location and Fun For Everyone!
9.6 out of 10, Exceptional, (31)
"Great location and super quiet. Even on a Labour Day weekend. Loved our stay. And our dogs loved the stay too. Would recommend"
Great Location and Fun For Everyone!
Gorgeous waterfront cottage on beautiful Bear Lake
9.8 out of 10, Exceptional, (55)
"The cottage is bright, fairly clean, and the kitchen has a good amount of dishes, pots and pans. The beds are comfortable as well. It would have been nice to have a working dryer for our mitts and hats. We noticed it had been down since October. Also, an area to hang winter clothes and matts to put winter boots on. We didn't want to put our wet gear directly on the floor. Knowing we were coming and we paid a lot of money to stay plus an additional charge for our fur baby which was more than...
Gorgeous waterfront cottage on beautiful Bear Lake
Lakefront 4-bdrm house for rent in the heart of Muskoka
9.8 out of 10, Exceptional, (7)
"Everything is good except no washroom in the basement,more kitchen towel."
The price is CA $499
CA $800 total
includes taxes & fees
Jun 2 - Jun 3
Lakefront 4-bdrm house for rent in the heart of Muskoka
Inn The Moment: A Bright and Cozy Getaway in the Heart of Muskoka
10.0 out of 10, Exceptional, (13)
"The cottage was beautiful. It had everything we needed. We enjoyed our walks every morning."
Inn The Moment: A Bright and Cozy Getaway in the Heart of Muskoka
Cozy Lakefront Cottage
9.6 out of 10, Exceptional, (9)
"Fell in love with this cottage from the moment we arrived. The setting is beautiful. The cottage itself is lovely and well maintained. It was comfortable and welcoming. Bianca was a wonderful host. Throughout the entire process she was available and helpful. Bianca was a pleasure to work with. We hated to leave. We look forward to returning again soon."
Cozy Lakefront Cottage
Lakefront Muskoka of Amazing Cottage
8.8 out of 10, Excellent, (8)
"Had a great time but they do need to let you know that they don't have plates and pots and stuff for cooking"
The price is CA $309
CA $484 total
includes taxes & fees
Jun 1 - Jun 2
Lakefront Muskoka of Amazing Cottage
Muskoka Lakeshore Cottage Bliss, Sleeps 16 in spring, summer, fall, 10 in winter
10.0 out of 10, Exceptional, (5)
"A group of 14 people were staying at the cottage. It is exactly as pictured. More than enough space for the group. The separation of the bedrooms from the kitchen/main floor was fantastic, people had their own space and were not disturbed by people chatting or hanging out in the kitchen/living room. The screened-in porch was amazing to have! We basically spent all of our time there; gorgeous view and allowed us to avoid the bugs! The kayaks/pedal boat were also a huge hit. There was a small...
Muskoka Lakeshore Cottage Bliss, Sleeps 16 in spring, summer, fall, 10 in winter
Muskoka Lakes Waterfront Cottage 10 Acres of Forest
9.8 out of 10, Exceptional, (24)
"A hidden gem in the woods."
Muskoka Lakes Waterfront Cottage 10 Acres of Forest
Lake Muskoka Executive Cottage
9.8 out of 10, Exceptional, (9)
"Stayed here with my family over Christmas. The cottage was well stocked with kitchen pots/pans and coffee. It was clean and welcoming. There is a sound system throughout the house for music and a huge smart TV. We also loved the fireplace and hot tub. The waterfront is quiet and beautiful. It’s is a great cottage."
Lake Muskoka Executive Cottage
Don't see what you're looking for?
See all available 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.

Windermere Vacation Rental Travel Info

Number of vacation rentals
10
Popular accommodation
Windermere cottages
Known landmarks
Muskoka Lakes Winery, Aspen Valley Wildlife Sanctuary and Muskoka Lakes Museum
International airport
Toronto, ON (YYZ-Pearson Intl.)

Other types of properties in Windermere you may be interested in

Windermere House
3.5 star property
8.8 out of 10, Excellent, (375)
"Beautiful Resort, friendly staff and so relaxing. Wonderful getaway."
The price is CA $199
CA $280 total
includes taxes & fees
Jun 2 - Jun 3
Windermere House
JW Marriott The Rosseau Muskoka Resort & Spa
4.5 star property
8.6 out of 10, Excellent, (867)
"Staff are friendly. Just the long wait on check in."
The price is CA $399
CA $564 total
includes taxes & fees
Jun 2 - Jun 3
JW Marriott The Rosseau Muskoka Resort & Spa
Residence Inn by Marriott Gravenhurst Muskoka Wharf
3.0 star property
9.0 out of 10, Wonderful, (1002)
"Great small hiking path near the hotel with good lake view. Room is well equipped with kitchen appliances if you plan to have a longer stay. "
The price is CA $263
CA $309 total
includes taxes & fees
Jun 25 - Jun 26
Residence Inn by Marriott Gravenhurst Muskoka Wharf
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windermere. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Windermere?

Yes, we have vacation rentals close to well known attractions in Windermere, or you can select a more remote option if you'd like a relaxing place to stay. Windermere is known for its lake views and golf courses. Make sure you have time to check out the bars and spas during your trip.

What are some of the best vacation home rentals in Windermere?

Lakefront Muskoka of Amazing Cottage: You might want to consider this vacation rental near Windermere, which is located on a lake and has a patio, a spa tub, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Windermere?

Expedia has 5 vacation rentals for your stay in Windermere.

What can I see and do in Windermere?

Explore the area and family-friendly sights such as Santa's Village, or get out into nature at a spot like Lake Rosseau. Other places in town to visit include Windermere Golf & Country Club and Windermere Marina.

What are vacation rentals like in Windermere?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Windermere. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for small groups.

Recent reviews of Windermere properties
Expedia verified reviews