Cottage holiday rentals in Grey Highlands

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.

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.

Woodski Retreat w/Heated Pool on 3+ Private Acres

This private mountain retreat is just 15 minutes from Blue Mountain, features 3.2 acres of beautiful scenery, a swimming pool and a renovated home for 10 guests (Max 8 adults). The house sits at the foot of a private 500ft mountain that is yours to explore all year around. Inside, there is a spacious home built for entertainment. Enjoy all-year fun at the property or head out to enjoy the amazing activities nearby. Only 5 minutes to the beach and 15 minutes to the best skiing in Ontario!

New and Cozy Cottage Minutes to Georgian Bay!

Conveniently located near the amenities, shops, and restaurants of downtown Meaford, our cozy stay is just steps from the Georgian Trail, a short walk from Georgian Bay, and a quick 20-minute drive from Blue Mountain Ski Resort. In Meaford and the surrounding areas, you'll find tons of local options to ski, bike, hike, swim, fish, golf and relax with family and friends. Embrace the Grey Highland's year-round beauty and enjoy the perfect blend of relaxation and outdoor excitement!

Little Red Cabin on the River

Bright and cozy, open concept cabin retreat overlooking Styx river in beautiful West Grey. Relax next to a quiet river on a large lot with elevated deck, natural wood-burning fire pit and BBQ. This all season get away is 2 hours from Toronto, perfect for small families or a small group. Recently updated, this cabin features simple, modern decor with a fully furnished kitchen for home cooked meals and baking. Also now includes WiFi and an outside wood burning, cedar barrel sauna.

Thistle And Pine Cottage

Relax and unwind with the whole family at this peaceful place in the country. The cottage is on 50 acres that you have full access to. Great for swimming, walking, biking, cross country skiing, and much more. This 1 bedroom plus pullout couch(with privacy) is complete with kitchen, bathroom, and livingroom, and swimming pond with beach and Fire pit area that overlooks the pond. Perfect for a family of 4 or a romantic getaway for 2. Find us on Instagram @thistleandpine.cottage

Waterfront Cottage by Bruce Trail

Welcome to this stunning waterfront , cozy ,4 season cottage located on the edge of a cliff surrounded by the lake on one side and Bruce trail on the other. This private oasis is perfect for couples or families w. older kids where you can connect to nature but still stay close to the city. Walking distance to Bruce trail, short drive to Sauble Beach or Wiarton for shopping and dining, 25 min drive to Lions Head, 45 min to Tobermory. It's time to plan your visit to Bruce!!!

Sanablue - Stylishly Un-Trendy since 1958!

Sanablue is a quiet & warm out of the way escape for your family ... that's right next to everything that's great about South Georgian Bay! See reviews for our track record! Just 91 barefoot steps to the edge of Georgian Bay IF YOU DARE!. A 4 min stroll to grab a coffee (or a bottle of wine). Just meters to Oakview Woods hiking trails & Wasaga biking trails. 10 min to Collingwood. 15 min to breathtaking Blue Mountain ..... Or just put your feet up & relax.

Beaver Valley School House •Hiking •Campfire •Pets

Enjoy this unique renovated School House as a generous, private space to gather as a family or group. Independent and remote, the School House is located in the beautiful Beaver Valley, near the Blue Mountains. With reliable, consistent high speed internet, and a close drive to groceries and towns, the School House is an ideal location to come together, ski, snow board, relax, connect, and explore the trails, and stunning views of the Niagara Escarpment.