Vacation rentals in Windy Island

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Top-rated vacation rentals in Windy Island

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Guest favorite

Place to stay in Wasaga Beach

5.0 out of 5 average rating, 195 reviews

Newly Built Woodsy Loft Retreat

Welcome to Woodsy Loft, a newly built retreat. A great spot for a getaway! A perfect home base for not just the beach and stunning walks into the sunset, but Blue Mtn, Scandinavian Spa, Collingwood, Cross Country Skiing Provincial Park and a brand new casino, all close by. Packed with amenities like screened in patio, XL bathtub, King size bed, 'The Frame' Smart TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

Nov 30 – Dec 7

G$30,503 GYD per night

Guest favorite

Apartment in Penetanguishene

4.88 out of 5 average rating, 380 reviews

The Haunted House Apt 302

As you pull into the driveway this 1885 Victorian towers above you, your mouth drops in awe of the size. Up the porch to enter a small front door, a dimly lit winding staircase creaks as you ascend to 3rd floor. Original architecture painted many times over oozes with history. 70 years ago the house was turned into apartments, unloved for many of those years, time has definately taken its tole, yet to the spirits within, their big old house still stands proud and distinguished in all its glory.

Apr 22 – 29

G$26,600 GYD per night

Guest favorite

Barn in Parry Sound

4.94 out of 5 average rating, 114 reviews

KING SIZE BED Barn style loft apartment private

Very private apartment that you will have all to yourself that’s above a barn style garage. It has everything you need for a very comfortable stay. The perfect little getaway situated near 2 lakes with public beaches and boat launches with in a short 3 minute walking distance or even shorter drive. Parry sounds 7 minutes away. there’s Restaurants near by and there’s also a 24 hour convenient store/gas station near by! The locations very nice to relax and explore what the area has to offer.

Sep 18 – 25

G$24,633 GYD per night

Guest favorite

Tiny home in Baysville

4.95 out of 5 average rating, 103 reviews

Grandview Lake Cabin, Muskoka

A cozy Tiny Cabin located just off the shore of beautiful Grandview Lake, In Baysville Muskoka. The perfect pine cabin for a couple looking to recharge, slow down and enjoy the simple pleasures in life with the tranquil surroundings of nature. Private access to lakefront with a canoe and acres of forests for exploring are only steps outside your door. Unplug and get back to nature or enjoy modern living on the lake. 45-60 minute drive from both Algonquin and Arrowhead provincial parks.

Sep 25 – Oct 2

G$30,278 GYD per night

Guest favorite

Cabin in Kearney

4.96 out of 5 average rating, 435 reviews

Cozy Creek-Side Cabin

Small cabin in the woods with many seasonal uses. There is over 1000 adjoining acres of mixed forest & fields. Over 300 acres of privately owned land by the host plus over 700 acres of attached public crown lots accessible through private holdings, perfect for outdoor enthusiasts/nature lovers, as a launch pad into Algonquin Park, or as a quite retreat into the forest. Winter Activities and Uses Include: snowmobiling, ice fishing at a large selection of local lakes, snow shoeing etc.

Oct 21 – 28

G$13,190 GYD per night

Guest favorite

Apartment in Wasaga Beach

4.95 out of 5 average rating, 339 reviews

The Upper Deck

The upper deck is an amazing one bedroom studio with a full newly renovated bathroom, a sweet kitchenette, an amazing king size bed, a 65 “ inch HD smart Samsung TV with a live edge counter- a great workspace or eating area. One wall is floor to ceiling windows -lots of great natural light!!! Outdoors has an amazing hot tub , rustic firepit area , a beautiful covered outdoor eating area with Bbq and you can hear the lake!! Note- the studio is a separate but is part of a house.

Feb 28 – Mar 7

G$27,758 GYD per night

Guest favorite

Guesthouse in Utterson

4.93 out of 5 average rating, 115 reviews

Lakefront Muskokan Log Cabin

In the heart of Muskoka on 3 Mile Lake. This cozy Log Cabin is set on private property. This studio room has all modern amenities which include 65” Smart TV, Netflix, microwave, keurig coffee maker, mini-fridge, toaster-oven, hot plate, barbecue and wall mounted fireplace. It has two beds and a full bathroom with seated shower. The waterfront has a shallow entry or you can jump in from the dock. A canoe, 2 kayaks & life jackets are for your use. End your night with a campfire.

Sep 27 – Oct 4

G$28,002 GYD per night

Guest favorite

Farm stay in Gravenhurst

4.97 out of 5 average rating, 370 reviews

Stix N Stones (Includes Light Breakfast & Kayaks)

Nestled in the woods on Walkers Point, this is a great opportunity to reconnect with nature. We promise when you leave you’ll appreciate the forest as much as the water that surrounds us. Although we are not on the water, we are a 3min drive to a semi-private beach. Kayaks & life vests included (& delivered). Snowshoes incl in winter. Light breakfast is yogurt & fruit. Short distance to renowned hiking trails, Hardy Lake Park, Sawdust City & Clearlake Brewery, Muskoka Winery.

Nov 5 – 12

G$33,885 GYD per night

Guest favorite

Cottage in Torrance

4.97 out of 5 average rating, 196 reviews

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Newly renovated 4 season waterfront cottage! Stunning views! Located on picturesque Nine Mile Lake. Over 70% of the lake is crown land. Perfect for kayaking and canoeing to enjoy all the beauty Muskoka is known for. We have kayaks a canoe and a paddle board for you to enjoy. Plenty of sun exposure on the dock you can swim all day long. Close to hiking and snowmobile trails. May 15-Oct 2 Minimum 6 nights with a Sunday check in.

May 20 – 25

G$34,912 GYD per night

Guest favorite

Cottage in Tiny

4.94 out of 5 average rating, 206 reviews

Bluestone

Bluestone is located less than 10 minutes' drive from beautiful Awenda Provincial Park in Tiny, Ontario. Every choice was made with guest comfort in mind. In the Summertime, take a short walk down a wooded path to Georgian Bay and perfect swimming, or explore a hiking trail and take in the natural beauty of the area. In Winter, enjoy skiing and snowshoeing locally, or stay in, put a record on, and cozy up by the fire. License #STRTT-2024-017

Nov 15 – 22

G$37,143 GYD per night

Guest favorite

Guest suite in Meaford

4.95 out of 5 average rating, 174 reviews

The Beach Button

Cute as a Button, this cozy home inspired by beach house vibes is nestled in the quaint town of Meaford. This town offers some of the most amazing waterfront to explore! 2 minutes east is a spacious public beach, 2 minutes towards the west is the beautiful Harbor or step out the door and enjoy a 3min walk down to the lake! This property is also located a scenic 25min to the famous Blue Mountain Ski Resort! and Scandinave Spa!

Feb 8 – 15

G$25,981 GYD per night

Guest favorite

Dome in Markdale

4.93 out of 5 average rating, 162 reviews

Forest Dome

This is an air b&b you'll definitely remember. Experience the magical feeling of waking up among the trees and birds. Feel the exhilaration of taking an outdoor shower. Enjoy the crackling fire and take the time to dream again. Nature, art, waterfalls and trails are all just outside your doorstep. You don't want to miss this peaceful retreat.

Jul 10 – 17

G$24,899 GYD per night