Windermere Holiday Rentals

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Holiday Rentals in Windermere

Touchstone Resort
4.0 star property
8.6 out of 10, Excellent, 233 reviews
"Lovely stay on Lake Muskoka with so many amenities. We enjoyed sunbathing on the large deck at waters edge, while others swam, used the free kayaks or canoes. Two swimming pools were also available. Dinner in the Touchstone Grill was excellent. "
The price is NZ$254
includes taxes & fees
5 Jun - 6 Jun
Touchstone Resort
Muskoka Lake Cottages
3.0 star property
7.2 out of 10, Good, 36 reviews
"The cottage was cozy and the view was beautiful!"
The price is NZ$249
includes taxes & fees
5 Jun - 6 Jun
Muskoka Lake Cottages
Renovated Waterfront Cottage on Three Mile Lake in the heart of Muskoka.
9.4 out of 10, Exceptional, 14 reviews
"To begin Holly was amazing! I’ve never booked with vrbo and she made it so easy for me, I requested an early check in and she got back to me right away, fortunately on this day she was able to accommodate the early check in. The cottage is clean, newly renovated and has a great view of the lake. We enjoyed the dock and fire pit tremendously. This cottage has everything you need for a couple, family or small group of friends. I highly recommend Holly and any of her rentals."
Renovated Waterfront Cottage on Three Mile Lake in the heart of Muskoka.
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Welcome to Falcon’s Nest, your 6 bedroom luxury all-season cottage retreat nestled on Lake Muskoka
10.0 out of 10, Exceptional, 22 reviews
"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
Log Cabin On the Lake B&B
10.0 out of 10, Exceptional, 9 reviews
"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 NZ$457
includes taxes & fees
10 Jun - 11 Jun
Log Cabin On the Lake B&B
260 feet of South West lakefront on Lake Joseph with all day sun
8.8 out of 10, Excellent, 3 reviews
"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
Brand new cottage on 3-Mile Lake in the heart of Muskoka
9.8 out of 10, Exceptional, 81 reviews
"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
Lakefront Muskoka Beautiful Cottage
9.0 out of 10, Wonderful, 9 reviews
"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 NZ$565
includes taxes & fees
8 Jun - 9 Jun
Lakefront Muskoka Beautiful Cottage
Cozy Cabin Overlooking Arrowhead Provincial Park and the Big East River
9.8 out of 10, Exceptional, 21 reviews
"My husband and I rented this cottage as a weekend getaway for our anniversary. The cottage was very clean and pretty much everything you needed for a relaxing time. Cottage is close to restaurants and amenities and neighbours are just far enough away to have privacy"
Cozy Cabin Overlooking Arrowhead Provincial Park and the Big East River
Cozy Waterfront Cottage on Muskoka River
9.0 out of 10, Wonderful, 4 reviews
"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
Cozy Cottage in Muskoka
7.6 out of 10, Good, 5 reviews
"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 NZ$491
includes taxes & fees
5 Jun - 6 Jun
Cozy Cottage in Muskoka
Great Location and Fun For Everyone!
9.6 out of 10, Exceptional, 31 reviews
"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!
Inn The Moment: A Bright and Cozy Getaway in the Heart of Muskoka
10.0 out of 10, Exceptional, 13 reviews
"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
Aux Box Muskoka**HOT TUB** Modern Bunkie
10.0 out of 10, Exceptional, 17 reviews
"The perfect cabin for a couple to enjoy a few days away in nature."
The price is NZ$402
includes taxes & fees
6 Jun - 7 Jun
Aux Box Muskoka**HOT TUB** Modern Bunkie
Lakefront Muskoka of Amazing Cottage
8.8 out of 10, Excellent, 8 reviews
"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 NZ$578
includes taxes & fees
5 Jun - 6 Jun
Lakefront Muskoka of Amazing Cottage
Lakefront 4-bdrm house for rent in the heart of Muskoka
9.8 out of 10, Exceptional, 7 reviews
"Everything is good except no washroom in the basement,more kitchen towel."
The price is NZ$955
includes taxes & fees
5 Jun - 6 Jun
Lakefront 4-bdrm house for rent in the heart of Muskoka
Muskoka Lakes Waterfront Cottage 10 Acres of Forest
9.8 out of 10, Exceptional, 24 reviews
"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 reviews
"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
Cozy Lakefront Cottage
9.6 out of 10, Exceptional, 9 reviews
"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
Gorgeous waterfront cottage on beautiful Bear Lake
9.8 out of 10, Exceptional, 55 reviews
"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
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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.

Other types of properties in Windermere you may be interested in

Windermere House
3.5 star property
8.8 out of 10, Excellent, 375 reviews
"Beautiful Resort, friendly staff and so relaxing. Wonderful getaway."
The price is NZ$335
includes taxes & fees
16 Jun - 17 Jun
Windermere House
JW Marriott The Rosseau Muskoka Resort & Spa
4.5 star property
8.6 out of 10, Excellent, 868 reviews
"Beautiful location. Friendly welcoming staff. The front desk staff were very helpful but some of them seemed to lack the knowledge to answer some of our questions about the activities advertised. Perhaps they were training new staff for the upcoming busy season. We were very pleased with the 2 hotel activities that we participated in"
The price is NZ$736
includes taxes & fees
13 Jun - 14 Jun
JW Marriott The Rosseau Muskoka Resort & Spa
Comfort Inn
2.5 star property
8.6 out of 10, Excellent, 993 reviews
"Great place to stay close to downtown Huntsville. Property was very clean and the staff was very friendly. I did find the beds a bit soft - seems like they could be updated. "
The price is NZ$134
includes taxes & fees
9 Jun - 10 Jun
Comfort Inn
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windermere holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windermere. 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 Windermere. 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 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 holiday 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 Windermere short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Windermere?

Yes, there are holiday rentals close to the most popular sights in Windermere, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Windermere has to offer?

Lakefront Muskoka of Amazing Cottage: This holiday home rental outside of Windermere is located on a lake, and has a patio, 1 hot tub and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals will I find in Windermere?

Expedia has 5 holiday 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 holiday rentals like in Windermere?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windermere. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for small groups.

Recent reviews of Windermere properties
Expedia verified reviews