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

4.92 out of 5 average rating, 300 reviews

Loft in Midland

Perch by the Bay - Downtown Midland / Private Loft

Luxury, Comfort & Georgian Bay Style. This first class rental, "Perch By The Bay", is located in Downtown Midland. Walk everywhere, park your car (free) & enjoy what Midland has to offer. Midland's boat harbour, is only minutes by foot. Live our lifestyle, enjoy our many festivals, professional theatre, artisans, culinary cuisine, etc! It's "sister" AirBnB is "Nest By The Bay" private loft at the rear of the building. 2 night min. preferred, 1 night by request. Not suitable for ages under 6

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

Place to stay in Wasaga Beach

5 out of 5 average rating, 301 reviews

Newly Built Woodsy Retreat - Your Perfect Escape

Welcome to Woodsy Loft, an ideal home base for not just the beach and stunning sunsets, but Blue Mtn, Scandinave Spa, Collingwood, brand new casino, all close by. Many bars, restaurants, beach and other things to do, within 5 min. Great place to stay in, too. Packed with amenities like screened in patio, XL bathtub w/ towel warmer, 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.

Apartment in Penetanguishene

4.88 out of 5 average rating, 464 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.

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 .

4.98 out of 5 average rating, 111 reviews

Cottage in Southgate

Luxurious Creek Retreat With Hot Tub

Welcome to this luxury cottage on the water. The perfect place to relax and unwind while listening to the waterfall and babbling brook flowing past only a few feet away. If you're looking for privacy and tranquility along with all the pleasures of a luxury stay then look no further. This property boasts a propane fireplace inside as well as one outside, in-floor heat and A/C. Fully equipped kitchen, two bedrooms with hotel quality mattresses and a bathroom that exudes high-end style and decor.

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.

4.95 out of 5 average rating, 122 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.

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

4.81 out of 5 average rating, 155 reviews

Tiny Beach Cottage

Beautiful, newly-renovated 6 bedroom cottage. All of the modern comforts of a home while maintaining the cottage feel you expect when trying to escape the busy city life. Situated on a "no exit" road resulting in a peaceful and quite area. Cottage has a central air conditioning and furnace ideal for all seasons. Featuring two large decks, perfect for outdoor dining or relaxing. Licence STRTT-2025-103

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Other great holiday rentals in Ossossane Beach

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.

4.95 out of 5 average rating, 293 reviews

Dome in Nottawa

One-of-a-Kind Dome Stay near Collingwood!

BrentRating, 5 stars2 weeks ago

While this is strictly speaking a review, let us start by publicly saying a warm Thank You! to Nikki and Joel for creating and sharing such a wonderful space to relax and unwind in! While perhaps lacking in some of the things we take for granted like plumbing, their space is transformative, showing new possibilities, combining beauty and functionality. While on the rustic side, it brings a chance to be more intimate with your surroundings. My wife was particularly in love with the swing chair and hammock right in the space. Highly recommended, very close to Collingwood and all it offers, a great escape.

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 stars1 day 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, 20 reviews

Apartment in Tiny

Cabin A in Wymbolwood Lodge

MelissaRating, 5 stars5 days ago

Cathy is so friendly and responsive. we absolutely loved our stay. It was quiet and peaceful with a beautiful private beach. A perfect weekend getaway :)

4.59 out of 5 average rating, 69 reviews

Cozy Beachfront Cottage: Private Beach, Hot Tub

MiguelRating, 5 stars2 weeks ago

The cottage is in a great location with a walk out to a beautiful large deck that leads to your own beach. It doesn't get any better. The property is spacious, modern, clean, well kept and cosy. The hot tub is a great feature of this property with an awesome view of the beach and star gazing at night. Internet performance is perfect for streaming on a big 85" TV and for working. This is a great property to create memories with family and friends. With lots to do from hanging out on the beach, swimming, BBQing, or exploring the local restaurants and shopping. You will not be disappointed.