Holiday rentals with lake access in Dufferin County

Spectacular Estate Pristine 100 Acres Private Lake

Unveil the beauty of our stunning home, where modern elegance graces a private 100-acre estate. Ideally located, you're just minutes from local attractions and essentials—including Westside Market Village (7 mins), Caledon Village Plaza (9 mins) and Orangeville Square (11 mins). Enjoy nature with Island Lake Conservation Area (12 mins) and Upper Credit Conservation Area just a 5-minute walk away. With parks, trails, shops, and dining all nearby, convenience meets tranquility in every direction.

Rustic Cabin on Private Pond

Our Rustic Beach House is simply furnished and set on you very own private pond with a private beach. It has electricity, does not have plumbing. Fresh drinking water is supplied. Bathroom is a clean, private outhouse and you have access to our guest shower facility on premises from 6-9 am/pm daily. As your Bed and Breakfast host we will personally greet you and check you in and always remain on property while offering you privacy. We are designed for a quiet, peaceful rustic getaway.

Spacious Basement Guest Suite

Welcome to Orangeville and to my lovely basement suite! Conveniently located walking distance to Island Lake Conservation Area (1 km) and downtown Orangeville (2 km) shopping, dining, business. Tons of hiking & outdoor adventures close by: Hockley Valley is 10 minutes away, Mono Cliffs Provincial Park, Monora Park...all just 5-10 minutes away. Headwaters Hospital is a 5-minute walk (perfect for doctors & pharmacists doing rotations), and the Ontario Fire Academy is a 5-minute drive.

The Manager's Cabin, RockHill Park

Experience this amazing historical RockHill Park, just a short 1 hour drive north of Toronto. Feel like you are away at a secluded destination in nature once you are tucked in our 122 acre property. The "Manager's Cabin" has hydro, which offers beautiful modern lighting, Kuerig coffee machine, and a good size small fridge. Have fun with all the outdoor activities enjoying the natural clear spring fed water, beach, and the amazing section of Bruce Trail adjacent to our property.

5BR Riverfront Retreat w/ Firetable, BBQ, and Deck

Welcome to my spacious riverfront retreat, perfect for up to 10 guests! This 5-bedroom, 3-bathroom home features 4 queen beds, 1 king bed, and a bathtub. Enjoy outdoor dining on the beautiful deck with a firetable, BBQ grill, and over 1000 ft of river frontage on 72 acres. Inside, you'll find a Smart TV, thermostat, washer/dryer, and ample parking with 6+ spots. Garbage bins are located in the garage for your convenience. Relax and unwind in this serene and well-equipped getaway

Walk to Downtown Orangeville | Free Parking & Game

Welcome to your perfect Orangeville getaway! This stylish 3-bedroom, 3-bath home is literally steps away from Downtown Orangeville’s best cafés, restaurants, shops, and local attractions. Family-friendly and designed for comfort, enjoy free parking, Smart TV, board games, a cozy coffee station and a fun popcorn machine for movie nights. Whether you’re here to relax, explore, or spend time with loved ones, this home offers the perfect mix of convenience, comfort, and location.

Country Oasis - 5 private acres with hot tub

Escape to the country and unwind. Just 1.5 hours from the city, this luxurious chalet sleeps up to 12 and offers a hiking loop, a 1-acre swimming pond, volleyball, ping pong, a trampoline. (Or work with ease thanks to high-speed wifi.) With ski clubs, Bruce Trail hiking, cycling, and snowmobile routes right outside the door, boredom is not an option. Venture up to Collingwood, hop down to Hockley Valley, or just soak up the tranquility from the hot tub.

Central OVille,3 bed Victorian, walk to Lake, pets

This 3 bedroom (4 beds), 1,500 sqft unit with new Gas Fireplace and central A/C sleeps 6 adults comfortably. Bedroom 1 has a queen-sized bed, another a double bed while Bedroom 3 contains two separate single beds. There is large and beautiful private deck and fenced back yard that contains a full-sized BBQ The unit contains: Washer and dryer (within the unit), hard-wood floors, and free high-speed unlimited internet and HD Cable.

Fabulous Family Retreat, 1hr from TO, Sleeps 8

Just 10 minutes to Hockley Valley Ski Resort. Located in the heart of Ontario's Headwaters region, this stunning estate home boasts 4 bedrooms and 4 bathrooms. Walk out the front door to a private path to the Island Lake Conservation which offers snowshoeing, trail walks or skating on the lake. Enjoy a luxurious stay with a home built for welcoming guests and making everyone feel at home.

Upper level 2 bdrm apt

Take a break and unwind at this peaceful oasis. In new house a 2 bedroom apartment suited for two or max 4 adults, located in conservation area with lakes, beaches, nature trails, horseback riding, hike, canoe or cycle in natures playground. In winter time downhill ski, cross country ski, skating, ice-fishing, snowmobile and much more. Please check the websites for details.

Beautiful Belwood Lake Campground RV’g

Spend warm, summer evenings relaxing in the great outdoors. Experience a world-class selection of facilities, spread across 200 acres of beautiful property. Find a place that’s all your own — where you can meet new friends, spend quality time with family, and make memories that will last a lifetime. Discover the gorgeous landscape that surrounds this place to stay.

Log Chalet | Private Lake+Games Room | 1hr Toronto

Wake up to lake views from every bedroom. Spread across 100 private acres in Caledon Village, this log chalet is your complete escape — private lake, kayak, fire pit, basement whiskey bar, and wildlife at your doorstep. Just one hour from Toronto.