Holiday houses in Ossossane Beach

4.87 out of 5 average rating, 411 reviews

Home in Meaford

Waterfront* Hot Tub* - Beachhouse Hideaway *Unique

This beach house was designed with relaxation and the enjoyment of togetherness in mind. Let your worries melt away as you slip into the warmth of this water side hot tub featuring stunning view across Georgian Bay and up the mountain side, as fresh snow falls around you. The open concept design makes this the perfect place to gather with family and friends w/ walkout waterfront patio and dock access for swimming. 2 min to downtown Meaford, 20 min to Blue Mtn, 1.5 hrs to Tobermory. Hiking Trails

4.97 out of 5 average rating, 120 reviews

Summer Getaway - 3 min walk to Beach, Clean & Cozy

Insta: @woodwardbythebeach 3min walk to the area’s most beautiful beach, sunsets & trails, you'll be sure to get lost in the serenity of the sand dunes year round Outdoor fire pit- s'mores included! Enjoy the BBQ, deck, & patio; the wine is on us! Fast WIFI for streaming movies or work from cottage Area is secluded yet central. 10min to Midland, close to Balm Beach - arcade, gokart, restaurant, & bar Ski/Hike/Snowmobile then unwind in a peaceful winterized home getaway with indoor fireplace

Apartment in Penetanguishene

4.92 out of 5 average rating, 253 reviews

The Haunted House Apt 301

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.

5 out of 5 average rating, 41 reviews

Home in Tiny

Tiny Beaches Getaway

Kick back and relax in this calm, stylish space. Nestled in a quiet neighbourhood only 9 minutes walking distance from one of the nicest sandy beaches ( Ossassane Beach) on Georgian Bay this Adult Retreat is a perfect getaway from the busy city life . Enjoy the turquoise waters ( you will think your are somewhere in Carribean) of Georgian Bay during the day and gather around the firepit out back on cozy summer nights to enjoy good conversation and drink in privacy surrounded by woods .

4.96 out of 5 average rating, 23 reviews

Home in Tiny

Luxury Cottage - The Lookout. Next to Balm Beach

Welcome to The Lookout, hosted by The Cawaja General Store! This cozy, 2-bedroom modern cottage is just a short stroll from beautiful Balm Beach on Georgian Bay. Designed with comfort in mind, it offers a private sauna, fire pit, heated bathroom floors, plush towels, eco-friendly soaps, and a fully equipped chef’s kitchen. Enjoy a spacious living room with a warm gas fireplace, HD TV, Wi-Fi, a variety of board games, and a handpicked book library. Every detail invites you to unwind and relax!

4.97 out of 5 average rating, 108 reviews

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

4.89 out of 5 average rating, 343 reviews

Loft in Midland

Nest By The Bay - Downtown Midland / Private Loft

Luxury, Comfort & Style. This one-of-a-kind rental, "Nest By The Bay", is located in Downtown Midland. Walk everywhere, park your car & enjoy what Midland has to offer. Midland Harbour is only minutes by foot. Live our lifestyle, enjoy our many festivals, professional theatre, artisans, culinary cuisine, seasonal events & so much more! See our other listing "Perch By The Bay", also at this same location. 2 nights min. preferred, 1 night by request. Listing not suitable for ages under 6.

5 out of 5 average rating, 10 reviews

Cozy Beachside Getaway – Steps from Balm Beach!

Experience the charm of our cozy 2-bdrm, 1-bath, cottage located just steps away from Balm Beach! Its prime location provides easy access to the stunning sandy shores and excellent swimming. Plus, you’re just a short walk from local restaurants, an arcade, and charming shops – making this location ideal for any season! In the winter, this cottage is the perfect base for adventures such as skiing and snowmobiling. Features: Bedroom 1: Queen Bed Bedroom 2: Queen Bed Living Room: Futon

5 out of 5 average rating, 182 reviews

Cabin in Bracebridge

Secluded Lakeside Retreat - Atkins Hideaway

Tucked in the heart of Muskoka, this handcrafted timber frame cabin rests alongside a scenic spring-fed lake, surrounded by 8 acres of private forest. Only 10 minutes from Bracebridge, enjoy serene lake life and natural beauty while remaining close to town amenities, local shops, and eateries. Enjoy private dock relaxation, cozy cabin comforts, and outdoor fires. A Provincial Park Day Pass is included (*security deposit required) for added adventure. Come relax, recharge and reconnect.

4.95 out of 5 average rating, 123 reviews

Apartment in Midland

Hosted by Nous Midland

Small-town charm at its best! Our centrally located apartment is the perfect home base for your small-town adventures. We're minutes from the unique shops and restaurants in downtown Midland and the Midland Harbour. There is plenty to experience; attend a local festival, take in a tourism site, hop onto the Trans Canada Trail System with your bike or snowmobile, attend a show/concert at the Midland Cultural Centre, or snowshoe through the Wye Marsh.

4.94 out of 5 average rating, 284 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-2025-008

5 out of 5 average rating, 41 reviews

The Hideaway Balm Beach Cottage

The Hideaway is a beautifully designed, four-season cottage with rest and relaxation in mind. Steps to Balm Beach with clear water and amazing sunsets. Walking distance to tennis courts, ice cream shop, restaurants, children's playground and arcade. Cottage has all the amenities, including a chef's kitchen, cedar barrel sauna, firepit, private backyard with outdoor furniture and bbq grill. Tiny Township license No. STRTT-2025-034

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Other great holiday rentals in Ossossane Beach

5 out of 5 average rating, 36 reviews

Bungalow in Tiny

Cottage in Tiny. License #. STRTT-2025-068

SiobhanRating, 5 stars9 months ago

Our family had a great stay at Romuald and Marta's for a week at the end of the summer. They have a beautiful, spacious home that is even nicer than the photos. The location is also wonderful, a nice wooded neighbourhood and a very short walk across the road to a beach shared with other local neighbours. At the beach they have a great set-up with umbrellas, beach chairs, kayaks, and a paddleboard. We also used the volleyball court that is there. Everyone in the area seemed quite friendly. Lots of space for everyone, stunning washrooms, nice spacious kitchen, outdoor dining, firepit. Can't think of anything that was missing. Awesome place, would definitely return.

4.79 out of 5 average rating, 34 reviews

Appleton Cottage by the lake - Georgian Bay

JosephRating, 5 stars12 months ago

Her cottage was in a private secluded cul-de-sac. We were suprised to find wonderful historical areas such as Discovery Harbour, Martyr's Shrine and Sainte-Marie among the Hurons close to the cottage. The neighbour's were friendly yet respected our privacy. My wife and I intention was to have a quiet private place to rest our galavanting souls after a long day of discovery. We found it here in this cottage. The beach was not far and was a wonderful after dinner stroll. The locals directed us to wonderful small local eateries along the way around the peninsula - from Wasaga beach, Thunder beach, to Penetanguishene to Midland. The cottage has all the amenities one could ask for in a cottage. Fe was responsive, had clear instructions and keeps a tidy cottage.

5 out of 5 average rating, 16 reviews

Redbrick Hideaway

MelissaRating, 5 stars22 months ago

We stayed with two families at Susie’s cottage and we had a great time. Lots of space for two small families. The cottage was super clean, everything was labelled and easy to find. The bathrooms were spotless and with three bathrooms no one had to wait for their turn. The backyard was huge and the kids had a lot of fun playing and running around. The best part of all was the beautiful beach just a few minutes walk away. We will definitely want to book again next summer.

4.89 out of 5 average rating, 9 reviews

The Peaceful Cottage at Tiny

AnnaRating, 5 stars11 months ago

amazing cottage , great location, friendly and responsive host. The whole family had am amazing stay, we are hoping to be back next year ! cottage was equiped with everything you might need . if you want a private place , nice beaches with lots to do in the area this place is for you ! we had a wonderful time! thanks neta ! 😀

5 out of 5 average rating, 28 reviews

Apartment in Midland

Hidden Gem

JoanneRating, 5 stars3 days ago

Truly a hidden gem! The apartment was as described and more - we immediately felt at home. Excellent bed, comfy couch, fully equipped kitchen even nice towels! Loved the outdoor space complete with BBQ. We have marked this as our landing spot when putting our boat on and out of the water in Midland - will be back for sure! Michelle was a very responsive and kind host.

4.95 out of 5 average rating, 21 reviews

Apartment in Tiny

Cabin A in Wymbolwood Lodge

OlaRating, 5 starstoday

Cathy and John are such lovely and kind hosts. The cabin was incredibly cozy, and the beachfront was absolutely stunning! The beach was spotless, and the water was crystal clear. We truly enjoyed our stay and will definitely be back! 😊

5 out of 5 average rating, 8 reviews

Guesthouse in Midland

Hillside Studio: Small Town Escape + Scenic Views

NathanRating, 5 stars1 day ago

Erica is an awesome host and was very accomodating! She was very responsive and had some great recommendations of things to see and do in the area. The studio is super modern and has everything you need for your visit to Midland. It's walking distance to downtown Midland and the Marina.