Welcome to Little Black Bear, a warm, winter-ready North Bruce retreat where privacy, comfort, and space come together in the best way. Set back on a quiet 2-acre wooded lot, this home feels like your own little winter hideaway—surrounded by tall cedars and evergreens, with the kind of stillness that makes you breathe deeper the moment you arrive. Whether you’re gathering with family, escaping with friends, or just craving a reset somewhere peaceful, this spot is built for cozy, unrushed stays.

Inside, the cottage opens into a bright, open-concept main living space that’s perfect for winter downtime. The living room is spacious and inviting, anchored by an ambient fireplace that makes movie nights, board games, and slow mornings feel extra special. Big windows bring in soft winter light and forest views, so even when you’re curled up indoors, you still feel connected to nature outside.

The fully equipped kitchen is designed for real cottage living—plenty of counter space, everything you need to cook comfortably, and a layout that keeps the chef part of the conversation. The kitchen flows naturally into the dining area, making it easy to share big breakfasts before hitting the trails or linger over long dinners while the snow falls outside. This whole main space is one big, comfortable hub for your group—no squeezing into corners, no stepping around each other. Just room to settle in.

Little Black Bear offers three generous bedrooms, all on the main floor, so the entire group can spread out without any stairs to worry about. Each bedroom is set up to feel calm and restful, with space to unpack and get comfortable for longer stays. One bedroom includes a dedicated workspace, ideal if you’re mixing a little remote work into your winter escape—or if someone just wants a quiet nook to read, journal, or take a breather while the rest of the group hangs out.

With two full bathrooms, mornings stay easy even with a full house. Whether you're rinsing off after a snowy hike or warming up after a day outdoors, everything is set up for comfort and convenience. The home is efficiently heated and fully four-season, so you can enjoy winter without feeling chilly indoors. Add in reliable treated drinkable water, and you’ve got the kind of practical comfort that makes a stay feel effortless.

There’s also a garage and extra storage space, which becomes especially handy in winter—room for boots, coats, sleds, hiking gear, or whatever your group brings along. And if you want to keep moving even when the weather is doing its thing, the cottage includes a small fitness/work area with a treadmill, great for a quick walk or run before settling in by the fire.

What really makes the space shine in winter is the balance: big, bright communal areas for together time, plus quiet corners and roomy bedrooms for privacy. You get the feeling of being tucked away in nature, while still having all the comfort and space of a proper four-season home. Whether your day is all adventure—snowy trails, quiet shoreline walks, lookout hikes—or all relaxation—slow cooking, fireside naps, and stargazing on crisp nights—Little Black Bear gives you the room to do it your way.

The Spry Shore community is a wonderfully friendly community with plenty of water access points, nature trails and privacy with large estate lots.

Venture to nearby towns of Lion's Head to visit the Farmer's Market, sandy beach, marina and the Lion's Head Lookout Bruce Trail trailhead. A little further North you can visit the National Park, including the famous glacial formed 'Grotto', then relax in the quaint town of Tobermory where you can dine and shop.

Native Land Acknowledgment
We acknowledge the traditional Territory of the Anishinabek Nation: The People of the Three Fires known as Ojibway Odawa and Pottawatomie Nations. And further give thanks to the Chippewas of Saugeen, and the Chippewas of Nawash, now known as the Saugeen Ojibway Nation, as the traditional keepers of this land.

Sleeps 8 (6 adults and 2 children, 12 and under)

Please note that there is a pet fee of $175 at this property.

Winter Weather Advisory
Weather in Grey-Bruce can be unpredictable. Snow clearing follows a set schedule and is not on demand. Travel during storms is at your own risk, and cancellations due to weather do not alter the cancellation policy.

House Rule – Booking Commitment
Please review the property details, location, and total cost before booking. We honour the cancellation policy as stated at the time of booking only. Cancellations for reasons unrelated to the property—such as cost, change of plans, or travel issues—will not be refunded outside of this policy.

Little Black Bear is professionally managed by our property care team, a group of almost-famous locals dedicated to ensuring you have a fantastic stay.

Here's what makes staying at Little Black Bear so unique:

1. Privacy: Little Black Bear resides on a private 2 acre lot in Northern Bruce Peninsula. The estate lots are home to some of the Peninsula's elite.
2. Location: the location is close to multiple Lake Huron access points, the sandy beach of Black Creek Provincial Park, central to Lion's Head Marina, The Bruce Trail, National Park and more.
3. The scenic route it resides along provides the perfect spot for cycling, running and enjoying the great outdoors.
4. The cottage itself is a spacious 2,100 sq. ft. bungalow - everything you need is on one floor
5. Affordability: we want families to enjoy their stay without overspending.
6. Explore: Book a private hike on the Bruce Trail with our certified Ontario Hike Leader.

This is the perfect location to get away from it all and enjoy some quiet time with family and friends.

You deserve this vacation!

STA license number NBP-2022-638.