Cottage holiday rentals in Grey Highlands

Serenity, Simplicity and Stone

This is a tiny cottage in a sleepy little hollow that opens onto the Georgian Bay. Inside, each stone was carefully chosen and the woodwork was built, piece by piece, by two craftsmen who are highly skilled and passionate about repurposing. It's an art that will leave you in awe; especially if you're worried about climate crisis. The coat hangers are upcycled 100-year-old railway spikes! If you're looking for luxury you will be disappointed but if you're a minimalist you're going to love it.

Vintage School House ~Hiking, Skiing, Pet Friendly

Gather with family or friends in this vintage 5 bedroom School House in the Beaver Valley. -Ideal location to come together, relax, & connect. -Central heat & AC. -Take in the spectacular views of the Beaver Valley. -Explore the Niagara Escarpment and lookouts of the Bruce Trail. -Relax and read by the fireplace. -5 min walk to our swimming pond with dock & beach. -Convenient drive to groceries and local villages. -25 min drive to the Blue Mountains. -Reliable, consistent high speed internet.

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.

Cozy Riverfront Cottage with Dock

Escape to our cozy waterfront cottage on the Nottawasaga River in Wasaga Beach! This bright, airy retreat comfortably sleeps 4 and features a large private dock and fire pit both overlooking the river plus modern amenities, outdoor dining area and BBQ. Enjoy direct river access from the dock for fishing and boating. Perfectly located just minutes from the main Beach 1 and a short drive to Blue Mountain Ski Resort, Collingwood, Creemore and the Wasaga Casino. Your ideal getaway awaits!

Sunset Cottage on Lake Eugenia -Hot Tub-4 Seasons

Well maintained/clean family lake front 4-bedroom cottage with sandy beach entry & 5" off the dock. We offer a large living room with a wood burning fireplace, dining room with full lake views, open kitchen, finished basement rec room with queen pull-out couch and laundry. Access to acres of privately owned forest land great for hiking, mountain biking, ATV’s, snowshoeing, close to the bruce trail, waterfalls and abundant nature. Our ideal guests are families with or without kids.

A Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi

30 minutes to Georgian Bay, 25 to Collingwood/Blue Mountain, and only 10 to Lake Eugenia's public beach. Our lovely, spacious, 5 Bed 5 bath retreat is nestled comfortably in the woods, convenient to almost every kind of activity and adventure. With 5 wash rooms and a large, INDOOR, jetted hot tub, it provides the perfect combination of convenience, relaxation, and outdoor adventure! BBQ, pool table, fireplace, fire pit, board games and high speed wifi. INSTA: @HIDDENHIDEOUTS

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

All-Season Cottage on the Lake

An entire cottage all to yourself right on the water of Lake Eugenia in the Grey Highlands. This fully furnished 3-bedroom cottage is equipped with a brand-new kitchen, appliances, wood burning stove, furnace and water heater. You'll also have FREE access to unlimited WiFi, so you can work or stay in touch, when needed. Our cottage is suitable for a great get-away with any group, family or friends who are looking for a peaceful and enjoyable holiday from their busy lives.

Bayview Oasis: Luxe Lakeside Escape w/ Pickleball

Welcome to Bayview Oasis, our luxurious lake house on Georgian Bay. Enjoy breathtaking water views, a modern kitchen with high-end appliances, a cozy basement with a pool table and bar, and a master suite with top-notch amenities. Outdoors, relax in the cabana with a pizza oven, fireplace, picnic tables, spacious patio, hot tub, and our new custom pickleball court. Whether it's a romantic getaway or family vacation, Bayview Oasis is the perfect retreat.