House holiday rentals in Grey Highlands

Close to Beach & Trails with Large Fenced in Yard

Whether you are looking to rest and recharge or head out on an epic adventure in the hills, this comfortable century home is the perfect base. Nestled in the quaint town of Meaford the home is walking distance to everything you need for a great stay. It has a large backyard, fire area, patios, laundry, stocked kitchen & two living rooms. The recently updated home is set up perfectly for families & medium sized groups. The large fenced in backyard is perfect for pets and a great space for kids.

A-Frame in the Woods of GeorgianBay, Muskoka

Welcome to our A-frame in the heart of Georgian Bay, Ontario! Perfect for family escapes and relaxing couples weekends in Muskoka. This cozy retreat has three bedrooms and accommodates up to six guests. With Six Mile Lake and Whites Bay just a stroll away, indulge in serene swims or explore the local golfing, breweries, and skiing at Mount St. Louis. Immerse yourself in nature's embrace while relishing the comforts of our picturesque A-Frame home—a perfect family getaway for every season!

Adorable — One Bedroom Guest Unit in Vaughan, ON

Enjoy a stylish and peaceful stay at this centrally located one-bedroom lower-level unit, perfect for both leisure and business travelers. With your private entrance, parking, and all the essentials, it’s your ideal home away from home. Features include a full kitchen, bathroom, internet, smart TV, one Queen and one sofa bed, and a functional workspace. Steps from FreshCo, Walmart, restaurants, and services. Minutes to Vaughan Mills, Canada’s Wonderland, Cortellucci Hospital and transit.

Studio Apartment

Discover the perfect blend of comfort and convenience in this cozy studio apartment, ideally situated in the vibrant heart of Caledon. Key Features: Prime Location: Steps away from shops, cafes, and parks. Modern Amenities: Spacious living area, and stylish bathroom. Natural Light: Large windows that fill the space with warmth and brightness. Community Vibe: Enjoy the friendly neighborhood atmosphere and local events. This peaceful retreat, offers everything you need. Don't miss out!

JJ’s small town country retreat

Take a step back in time to this old farm house. Located on the corner of our little town called Badjeros. This house was built in the 1930s and it’s been in our family for over 80 years. Since then there has been numerous upgrades to the house as well as a large 1200 square foot open concept addition built onto the existing house. While out in the country, this house is central to many attractions in the area 1.5 hours south of Toronto/GTA. Blue Mountain/ Collingwood is 30 minutes north.

Kiss & Bond Water View Colpoys Bay 4 -Seasons

Hello,, I'm the owner of a newly built home, that I hope I will provide first-rate, memorable experiences for my guests, I'm a nurse for over 30 years, and I love to explore. Im an animals lover, I'm also a mother of 3 boys and have been married for 33 years ,being outdoors is one of my favourite activities, snowmobiling, hiking. I've owned our cottage for 10 years and we decided to rebuild , to enjoy the beautiful views of Colpoys Bay and in the back yard the Bruce Pennisula escarpment

The Post Office Motel Boutique

Where luxury and style meet relaxation! The Post Office Motel is a boutique experience with all the luxuries of a day at the spa in peacefully designed space intended to send you straight into vacation mode. Step out of your car and right into the cutest hidden gem of a town known as Kimberley. Located steps to TWO undeniable restaurants, run by top chefs; Justin’s Oven & Hearts Tavern. Georgian Trail at your door step, 20 min to Blue Mtn, 15 min to Thornbury

Williamsford Blacksmith Shop

Make some memories at the historic stone blacksmith shop built 1888. Located in Williamsford, Ontario. Conveniently located to the historic sites, waterfalls, the Bruce trail, rail trails for hiking and snowmobiling. Short 20 minute drive to Owen Sound. Sauble Beach 40 minutes. Tobermory drive 1 hr 1/2. Markdale 20 minutes. Enjoy the sites surrounding or a peaceful night by the campfire with campfire wood provided.

Newly Renovated! Charming Beaver Valley Farmhouse

Quintessential Ontario 4+ bedroom century old farmhouse sitting on three private acres, comfortably updated and perfect for a quiet country getaway. Minutes from Lake Eugenia, Bruce Trail hiking and Beaver Valley Ski Club. 30 minutes to Thornbury, Collingwood, and the Blue Mountain. Enjoy the Grey Highland outdoors and relax by the wood burning fire.