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Holiday houses in Windy Island

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Holiday rentals for every style

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Popular amenities for Windy Island holiday rentals

Kitchen
Wi-Fi
Pool
Free parking on premises
Air conditioning

Other great holiday rentals in Windy Island

Top Guest favourite
Home in Georgian Bay
4.99 out of 5 average rating, 86 reviews

A-Frame in the Woods of GeorgianBay, Muskoka

BecciRating, 5 stars2 weeks ago
We had a wonderful time celebrating our friend’s bachelorette. We’ll definitely have to come back one day when it’s a little warmer!
Top Guest favourite
Cabin in Lake of Bays
5 out of 5 average rating, 65 reviews

Cozy Waterfront Muskoka Cabin

ShaneRating, 5 stars3 weeks ago
Fabulous cottage! Amazing view of the lake from both inside and out on the dock. We enjoyed cooking on the bbq grill in the evenings. Everything was clean and worked perfectly. Matthew was super responsive to any questions I had. Also close to Algonquin so was nice to spend a day there. Can’t wait to stay here again. Thank you for being wonderful hosts :)
Guest favourite
Cottage in Parry Sound
4.74 out of 5 average rating, 136 reviews

Muskoka Clearwater Cabin & Sauna

AshleyRating, 5 stars1 week ago
What a gem! This lovely cottage was everything we wanted. Private, clean and super cozy. The view from the deck steps away from the back porch was absolutely beautiful. Douglas was very friendly! His response time was very quick to any questions and he made sure we had everything we needed. His recommendations for around the area were super helpful too. Definitely recommend!
Top Guest favourite
Cottage in MacTier
5 out of 5 average rating, 17 reviews

140 Acre Secluded Cottage Retreat 2Br+1 in Muskoka

ChristianRating, 5 stars1 month ago
One of the most beautiful properties I’ve ever stayed at. Matt is great to deal with. The cottage was awesome and Dave the neighbour is super helpful and nice. Don’t be scared of river crossing it was smooth and seamless and made everything even more fun. Matt is a good guy and helpful with anything that comes up. The property is full of hiking trails and has awesome water access, great fishing, beautiful spot for a coffee in the morning. The deck is perfect for watching the sunset and the screen room is a great getaway if a little rain rolls through. All in all I’m extremely pleased with my stay in all aspects. Highly recommend.
Guest favourite
Cottage in Port Severn
5 out of 5 average rating, 35 reviews

Relax at Lakefront Follie’s Cove Cottage

MeghRating, 5 stars10 months ago
This cottage is perfection. Liane & James are just SO lovely. If you're reading this, don't look any further. Just book it. We couldn't have had a better week at Follie's Cove. The cottage was the perfect mix of modern and rustic. Clean, comfortable, and thoughtfully equipped. We felt at home instantly. The sunroom was the perfect chill spot for us and our two big dogs to get out of the sun/rain without feeling cooped up indoors. The beach was heaven for our dogs, and on a quiet end of the lake, so we saw few other people all week. The quintessential Muskoka experience! Liane and James were *beyond* wonderful. They set us up with a ton of breakfast food and desserts. Even offered to return the day after check-in to drop off more coffee. It truly felt like renting from friends. Highly recommend renting the pontoon boat from them and puttering around the lake. Wish I had more space to gush about the space and their incredible hospitality. We would book again in a heartbeat!
Guest favourite
Cabin in Whitestone
4.94 out of 5 average rating, 71 reviews

Cute Red Pine Bunkie with breathtaking water view

AndréRating, 5 stars8 months ago
I've just moved to Canada and this my first trip away from Toronto. The place, the hosts, the experience... all of them amazing. If you're visiting in October, make sure you bring extra bedding with you as it gets very cold (for a Brazilian lol). I'm definitely coming back.
Guest favourite
Cottage in Parry Sound
5 out of 5 average rating, 11 reviews

The Flagstone Cottage (A Lakefront Oasis)

KateRating, 5 stars7 months ago
What a glorious setting! Peaceful location with nature all around. We didn’t see or hear any neighbours - utter tranquility compared to our usual hectic schedule/ semi-urban surroundings. The house was easy to find with clear instructions; there were thoughtful additions such as a full log basket, plenty of loo roll, laundry detergent, basic cooking supplies like oil/ seasonings and extra towels were available if required. Clearly a lot of thought had gone into making it homely. Host was responsive and helpful with recommendations and instructions - even maps of the best canoeing spots! We had a very peaceful stay and teenage kids loved it - even though it was autumn, we still enjoyed the lake, swam, hiked, went canoeing, and toasted marshmallows in the fire pit. If you’re looking for a city rush with lots of buzz, look elsewhere; for peace, beauty and the outdoors immediately available, this is a great spot!
Guest favourite
Cabin in Parry Sound
4.78 out of 5 average rating, 121 reviews

Fancy camping in Massassauga Provincial Park

KateRating, 5 stars8 months ago
What a gem. This is a beautifully rustic spot in the woods for a gentle getaway on the water. There’s a bit of a scramble up a hill from the brand new dock (with amazing swimming and lovely afternoon sun!) to a sweet little cabin - everything you need for a comfier-than-camping holiday. There’s all the kitchen basics you need, and the wood stove makes it super cozy. The lake is quiet and the neighbours friendly. It’s a great spot for a lazy day in the dock, or a more adventurous day trip into Massasauga provincial park. Geoff was very responsive when the power went out and offered to come up to fix it right away. But we preferred to spend our last night in the warm glow of candlelight and wood stove. Highly recommend.
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