Guesthouse holiday rentals in South Bruce Peninsula

Brookside Cottage - Charming Rural Getaway Mulmur

Our cozy guest house, situated in the Headwaters region, has it all! Close to hiking,golfing,biking,skiing. XCski/snowshoe from your door! Big skies for astronomers and astrophotography! We offer 32 acres of forest and fields for walking and taking in the magnificent views. The area boasts fine restaurants, boutiques, markets and artisans. Minutes to Mono Cliffs, Boyne, Mansfield Ski Club and easy driving to Blue Mountain and Wasaga Beach. Ideal for couples, solo adventurers or a small family.

Location · Family · Cleanliness

Waterfront Sunrise Cottage

Private waterfront cottage 15 mins north of Owen Sound on the crystal clear waters of Georgian Bay. With a 150 feet of shoreline shared only with a neighbouring cottage, enjoy the stunning sunrises, relax on a lounger, go for a swim, kayak, paddle board, go fishing or 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.

Family · Location · Checkout

Cozy, quiet, clean cabin with wi-fi and fire pit.

Welcome to Penny Creek. A simple cabin just south of Durham. A private location surrounded by ponds, streams and forest - yet close to many day adventures should you want to explore beyond the property. Nearby amenities include restaurants, grocery, lcbo, fuel, coffee and shopping . An open concept space that offers one queen bed and a pull out sofa. Full kitchen and bath. Picnic tables, Fire pit and bbq. Excellent hiking trails nearby. Easy access to ofsc (snowmobile) trails!

Family · Location · Cleanliness

Cozy Collingwood Retreat | Walk to Beach & Cafés

Enjoy a relaxing getaway in a cozy, newly renovated retreat in a prime Collingwood location. Walk to great cafés and restaurants, stroll down for sunset swims at Sunset Point Beach, or take a short drive to the trails, skiing, and village at Blue Mountain Resort — all less than 15 minutes away. Perfect for couples, friends, or solo travelers looking for a cozy base to explore Collingwood and the beautiful Georgian Bay area. Licensed through the Town of Collingwood.

Family · Location · Getting around

Parry Sound Bunkie |Dock, BBQ, Firepit & Pets

Escape to Hemlock Cabin, your private fall lakeside retreat. Wake to sunrise views over vibrant foliage, spend crisp autumn days kayaking, hiking, or enjoying the calm lake, then savor BBQ dinners on the covered patio. End evenings by the fire pit under starlit skies 🔥. With cozy interiors, A/C, and space for couples or small families, this rustic-meets-modern gem is perfect for leaf-peeping, relaxation, and making Muskoka memories. Book your fall getaway today!

Location · Value · Parking

Entire Guesthouse - Forest Retreat, Starlink WiFi

Relax and unwind at this private getaway surrounded by peaceful woodland. California King bed and blackout curtains so you can ease into your morning with birdsong and the scent of fresh forest air. Refresh with a hot shower or relax in a clawfoot tub in your own spacious private bathroom. 3 acres of private woodland is yours to enjoy with easy access to the scenic Bruce Trail. Free parking, fast Starlink Wi-Fi, and a 50" Smart TV for cozy movie nights in.

Family · Value · Quiet

Bunkie in the Country

Now Open! Welcome! The bunkie has a great view of the sunrise. It's a quiet rural area (please note it is a GRAVEL road). Good for couples, solo adventurers, hunters, someone looking to be outside of town. The bunkie is located approx. 30 feet behind our home. For allergenic reasons and safety of animals, we do not allow pets. May not be suitable for those with mobility issues (small hill & stairs). The bunkie has heat and A/C!

Location · Value · Amenities

Cedar Springs Guesthouse: peaceful, dog friendly

Cozy, newly renovated guesthouse on 20+ acres of private, tranquil land on the beautiful Bruce Peninsula. Fibre-optic internet 🛜 Private fire-pit 🔥 Direct snowmobile trail access ❄️ Plenty of parking space for trailers 🛻 🚤 Just minutes from Oliphant Shores (2 min), Sauble Beach (7 min), and multiple Bruce Trail access points. Perfect for a peaceful retreat and outdoor adventures!

Family · Location · Air conditioning

Private Studio Near Sauble Beach & Trails

Private studio apartment on a beautiful 3-acre wooded property at Dreamers Writing Farm in Hepworth. Includes a full kitchen, bathroom, living area, TV, and gas fireplace. Self check-in. Access to shared outdoor spaces with gardens and animals. Located 7 minutes from Sauble Beach and close to trails, golf, and Nordic skiing.

Location · Family · Comfort

Owen Sound Coach House - First Floor (2-2)

In the heart of Owen Sound. Centrally located at the mouth of the harbour. Gorgeous meandering paths, fishing, and sight seeing. This 2 bedroom unit is spacious and on the main floor. Ample parking and convenience to all amenities.

Value · Family · Amenities

Applewood Cottage Dyers Bay

Waterfront, road in between Cottage in Scenic Dyers Bay, on Bruce Trail. Overlooking the blue sparkling waters of Georgian Bay Come and enjoy beautiful sun and moon rises over the water Air condition in upstairs bedroom

Family · Location · Indoor spaces