Holiday rentals in Hillsdale

The Beach House, Georgian Bay, Beach View w/ Sauna

New!! A rare and stunningly designed cabin overlooking a semi-private beach on Georgian Bay. This tranquil 4-bedroom, 2-bathroom retreat is surrounded by trees with breathtaking views of the pristine bay. Every detail has been thoughtfully curated for your ultimate enjoyment. We include all linens, towels, sheets, firewood for in/outdoor fires, olive oil, salt, pepper, a fully equipped kitchen with utensils, PrimeTV, Netflix, Sonos, and more. Additionally, we are taking bookings for 28+ nights.

Lakefront Family-Friendly Cottage on Trails

Four-season family-friendly cottage on 2.5 acres of natures best including wooded trails and a private lakefront and Hottub. Summer: Situated on 156-feet of lakefront. The lake is shallow and warm, perfect for families to enjoy. Equipped with a BBQ, Two fire pits and a lakeside beach shack for guests enjoyment. 30 Minutes from Barrie, Midland, and Orillia. ~ 75-minutes north of the GTA. Winter: Bonfires, frozen lake, direct access to OFSC Trails. Short drive to four well known ski resorts.

Off-grid Glamping Dome Nestled in the Woods

Welcome to our private campsite in Utopia, ON. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (summer only), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation Area, Nottawasaga & golf courses. Wasaga Beach is 30 min away.

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.

Warnica Coach House

Welcome to the Warnica Coach House! This unique and historic property will not disappoint! Built by George R. Warnica in 1900, this spectacular property was the recipient of the Heritage Barrie award in 2018. The Coach House where you will stay, once housed horses and carriages, has been completely renovated top to bottom in 2023 with the finest touches. We are centrally located with a 30 second drive from the 400, and an 8 minute walk to the waterfront, restaurants, and downtown fun.

Muskoka Stunning Cottage On Little Lake

Surrounded by Little Lake, this gem provides a relaxing getaway with amazing water views. Spend your days peacefully rowing on the lake or having a picnic on the private beach, and your nights settling by a crackling fire. The home itself is plenty spacious for unwinding and getting a good night's sleep, views all-inclusive. Explore Port Severn Park right next door and play around in the public beach and splash pad. For more adventure, hike the beautiful Georgian Bay Islands National Park.

Lost in Hillsdale | Heated POOL | Near Horseshoe

🏡🌲 Lost in Hillsdale | Spacious Getaway Near Horseshoe Valley Welcome to Lost in Hillsdale — a bright and spacious 4-bedroom retreat perfect for families and groups. Enjoy separate living and family rooms, a fully equipped kitchen, and plenty of space to relax and gather. Just 10 minutes from Horseshoe Valley and 20 minutes from downtown Barrie, with a summer pool and parking for 6–7 cars, this home is ideal for both adventure and relaxation. Unwind, explore, and feel right at home.

Ski, Swim, Soak, Boat & Golf

Renovated 2 storey cottage overlooking beautiful Orr Lake. Ski at Mt. St. Louis Moonstone or Horseshoe Valley. Both 13 minutes away. A heated swimming pool in the summer and a hot tub all year. Canoeing, kayaking, paddle boarding or golfing across the street. Fully equipped kitchen. Livingroom includes an overhead projector, plus as a second floor Family room with a Wet Bar. 5 bedrooms, 7 beds, & 3 Baths. Max occupancy: 10 adults or 12 including children under 13. Parking for 5 cars.

The four season Mount St. Louis hideaway

Escape to this Mount St. Louis hideaway, a private two-acre country retreat tucked among mature trees just minutes from Mount St. Louis Moonstone. This four-season getaway blends rustic charm with elevated comfort, Perfect for ski weekends, family escapes, or relaxed group retreats. Wake up surrounded by nature, spend the day on the slopes or trails, and end your evenings soaking under the stars in the private swim spa! Make Endless memories at this unique and family-friendly home.

Newly Built Woodsy Retreat - Your Perfect Escape

Woodsy Loft, an ideal home base for not just the beach and stunning sunsets, but Blue Mtn, Scandinave Spa, C-wood, brand new casino, all close by. Many bars, restaurants, beach and other things to do, within 5 min. Great place to stay in, too. Packed with amenities like screened in patio, XL bathtub w/ towel warmer, King size bed, 'The Frame' TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

Welcome to our cozy, modern condo in Horseshoe Valley — the perfect destination for families and groups of friends seeking adventure, relaxation, and unforgettable memories. Just a 2-hour drive from Toronto, our condo offers a prime location to experience it all. Whether you're hitting the slopes, unwinding at the Nordic spa, or exploring the outdoors with mountain biking, golf and tree-top trekking, you'll find everything you need for a perfect getaway.

Orr Lake Oasis

Sit, kick back, laugh & relax in this calm, stress-free, pet-friendly, stylish space with family and friends. Enjoy the great cottage views, games and much more. Drink your favourite drink by the hot tub or by the fire pit overlooking the lake. Take a steam in the barrel sauna just a hop away or take a walk on the local trails. Shop and dine at a tasty local restaurant 10 minutes away or drive out to the city of Midland just under 20 minutes