Cottage holiday rentals in Owen Sound

Cosy and modern cottage on beautiful Georgian Bay

Enjoy panoramic views of Georgian Bay from this charming modern cottage on Paynter's Bay. Only eight minutes from Owen Sound, our cottage also borders on the quiet and beautiful Hibou Conservation Area where you can enjoy birding, hikes in forest and shoreline, and a great sandy beach and modern playground for the kids. Cuddle up next to the gorgeous modern Morso woodstove. Adventure awaits you with lots of skiing, biking, snowmobiling and the waterfall wonders of the Niagara Escarpment nearby.

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!

Red Sky Lakehouse - Waterfront Oasis On Lake Huron

Rejuvenate at Red Sky—a spectacular waterfront cottage on the shores of Lake Huron in Ontario’s remarkable Bruce Peninsula. Whatever your style of holiday, you’ll find it here. Enjoy privacy, shallow warm waters, and world-renowned sunsets—all from the comfort of this peaceful oasis. Or use Red Sky as your home base to explore national parks, sandy beaches, and legendary hiking and ski trails, all within a 30-minute drive. Experience Canadian cottage country at its finest, in every season.

Water's Edge - 4 Season Cottage

Comfy & cozy 3 bedroom year round cottage on the shores of Georgian Bay. Sleeps 6, washer/dryer, full kitchen w/dishwasher, living & dining w/fireplace, A/C, deck, BBQ, firepit & hot tub. Suits families with older children & couples. Lots of shopping, live entertainment, artisans & exquisite local fare. 30 min drive to Blue Mountain Village & the Spa. Close to the Bruce & Georgian Trails. Spectacular views of The Bay, The Blue Mountains and the best sunrises with your morning coffee.

Georgian Bay Waterfront Oasis

Waterfront Cottage 15 mins north of Owen Sound on the crystal clear waters of Georgian Bay. We have 150 feet of private shoreline. Enjoy the east facing view and stunning sunrises, relax on a lounger, go for a swim, fish off the shore or in the small row boat, have a camp fire and stargaze. Use our cottage as a jumping off point for many hikes along the Bruce Trail, Sauble Beach (35min), Tobermory (70min) and many more. Or just work from here while enjoying the great view and wifi.

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