Sweepstakes Luxury Waterfront - Hot Tub & Tennis/Pickle Ball | Cottage in Tobermory, Canada

Perched directly on the water’s edge, Sweepstakes is a one-of-a-kind luxury retreat where modern elegance meets Ontario’s rich maritime history - named after the famous shipwrecks that lie in Big Tub Harbor. With 2 waterfront private docks, kayaks, a pickleball/tennis/basketball court, brand-new hot tub, and outdoor living spaces designed for both relaxation and entertainment, this property offers more than just a stay — it offers an unforgettable lifestyle experience.
Sweepstakes Waterfront Luxury is more than a place to stay — it’s a destination. Set directly on the water’s edge with a private dock and panoramic lake views, this newly reimagined estate blends modern design, high-end finishes, and ample amenities into an unforgettable retreat. Every element — from the brand-new hot tub and professionally landscaped grounds to the custom games lounge and private pickleball court — has been designed to provide guests with the ultimate in relaxation, recreation, and refined living.
The property has been fully upgraded from top to bottom to create a true luxury escape. Inside, you’ll find a bright open-concept floorplan, rustic indoor fireplace covered in cobblestone, and flooded with natural light from oversized windows that frame uninterrupted waterfront views.
The main living room features designer furnishings, a sleek modern fireplace, and curated décor that balances beachy feels with comfort. Every seating area is designed to make the view the focal point, so whether you’re enjoying a morning coffee or evening cocktail, the water is always in sight.
A state-of-the-art kitchen with premium appliances, beautiful countertops, custom cabinetry, and a generous island perfect for both cooking and entertaining. The kitchen is fully stocked for gourmet meals, from quiet family dinners to celebratory feasts.
Each bedroom has been styled as a private sanctuary with hotel-quality linens, plush mattresses, and sophisticated décor. Bathrooms are spa-inspired, offering rain showers, and designer fixtures that elevate your daily routine into an indulgence.
The exterior has been completely transformed with brand-new landscaping and a thoughtful design that makes outdoor living as luxurious as the interiors. Step directly into the water for a morning paddle, afternoon swim, or sunset cruise. Paddleboards are provided so you can explore the shoreline at your leisure. A brand-new spa tub set against the backdrop of the lake — the perfect spot to unwind beneath the stars or start your day with a breathtaking sunrise. Enjoy your very own private court that brings the resort experience to your doorstep, perfect for friendly games with family and friends. There is endless things to do here like enjoying the newly converted garage that has been transformed into a stylish entertainment space, complete with games and activities for all ages, ensuring fun no matter the weather. Sweepstakes is located right at the ship wrecks so you can go diving, swimming, or paddling right over all of the famous shipwrecks!
Enjoy multiple seating areas, an al fresco dining setup (inside and out!), brand new BBQ, provide endless opportunities to gather, relax, and take in the serene setting.
Staying at Sweepstakes places you in the heart of one of Ontario’s most storied waterfronts. Just a dive off the dock - away lies Big Tub Harbour, famous for its crystal-clear waters and well-preserved 19th-century shipwrecks. Experience schooners resting beneath the surface, silent witnesses to Canada’s maritime past. It’s a rare chance to connect luxury with history — enjoying cutting-edge amenities in a location steeped in timeless heritage.
During your stay, the entire property is exclusively yours to enjoy. That includes:
Full access to the home – every bedroom, infloor heating in both bathrooms, and living space is private to your group.
Gourmet kitchen – stocked with cookware, dishes, and essentials for preparing meals.
Private waterfront dock x 2! – launch the provided paddleboards (1 on site) kayaks (2 on site- with life jackets), take a swim, or simply lounge by the water.
Brand-new outdoor hot tub – available year-round for relaxation under the stars.
Pickleball court/tennis/basketball - fully lit at night – your own private court, perfect for morning matches or evening fun.
Games room – located in the newly renovated garage, featuring entertainment for all ages.
Outdoor spaces – beautifully landscaped grounds with multiple seating areas and a fire pit for evenings by the lake.
On-site parking – plenty of space for you and your guests.
From the moment you arrive until the time you check out, our team at Out of Office Collective is available to ensure your experience is seamless. Whether you need help with check-in, a local recommendation, or assistance during your stay, we’re just a message away.
Sweepstakes is proudly managed by Out of Office Collective, a hospitality group committed to setting the standard for luxury short-term stays. Our core values are hospitality, excellence, and attention to detail. From the moment you book, our team is available to assist with planning, offer local recommendations, and ensure that your stay exceeds expectations. We believe luxury isn’t just about beautiful spaces — it’s about peace of mind, care, and unforgettable experiences.

Sweepstakes Luxury Waterfront - Hot Tub & Tennis/Pickle Ball is located in Tobermory. Sweepstakes Luxury Waterfront - Hot Tub & Tennis/Pickle Ball provides accommodation, featuring Sports/Activities, Fireplace/Heating, Barbecue/Outdoor Cooking, among other amenities. This Cottage features Sports/Activities, Fireplace/Heating, Barbecue/Outdoor Cooking, to make your stay a comfortable one.

Sweepstakes Luxury Waterfront - Hot Tub & Tennis/Pickle Ball has 5 Bedrooms , 2 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have rated it 2, and VRBO labeled it a top-rated Cottage because of the excellent services rendered by the owner or manager of this Cottage, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Cottage has a friendly neighborhood, and the Tobermory has interesting places to visit. If you want to learn more about the Cottage in Tobermory, such as places to visit and things to do nearby, you can check below to learn more.