Holiday rentals in Hillsdale

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Top-rated holiday rentals in Hillsdale

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost

The entrance features double doors in a dark finish, adorned with elegant seasonal wreaths. Flanking the doors are decorative wall art pieces. A small bistro table with two chairs is positioned on a stone patio, complemented by potted snake plants and decorative pumpkins.

Home in Barrie

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

Our luxury home rental is located in one of the best neighborhoods in Barrie. Secluded neighborhood surrounded by forest. 5 min to HWY 400 8 min to Downtown Barrie 11 min to Snow Valley Ski resort 40 min to Blue Mountain & Wasaga Beach 25 min to Friday Harbor Resort Free WiFi-Cable & Parking Perfect home for families and large groups. Newly renovated home, with beautiful large outside area and swimming pool. Accommodates up to 9 guests. Pool open May 31 (Solar heated) Pool closes Sept.7

LocationValueQuiet

4.9 out of 5 average rating, 145 reviews

Top guest favourite

A charming cottage is showcased with a stone facade, set against a backdrop of lush trees. A welcoming front entrance is framed by steps leading up to a porch, while a well-maintained lawn and walking paths enhance the inviting outdoor space.

Cottage in Elmvale

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.

LocationFamilyAir conditioning

4.98 out of 5 average rating, 57 reviews

Top guest favourite

The exterior of a modern cottage is framed by tall trees and colorful foliage. A spacious deck wraps around the cottage, providing outdoor seating options. The gravel pathway leads to the entrance, surrounded by natural landscaping and decorative stones.

Cottage in Tiny

Fall Escape - dazzling colours & stunning beach

Insta: @woodwardbythebeach 3min walk to the area’s most beautiful beach, sunsets & trails, you'll be sure to get lost in the serenity of the sand dunes year round Outdoor fire pit- s'mores included! Enjoy the BBQ, deck, & patio; the wine is on us! Fast WIFI for streaming movies or work from cottage Area is secluded yet central. 10min to Midland, close to Balm Beach - arcade, gokart, restaurant, & bar Ski/Hike/Snowmobile then unwind in a peaceful winterized home getaway with indoor fireplace

ValueFamilyAmenities

4.97 out of 5 average rating, 133 reviews

Guest favourite

A spacious common area features a large, light-colored sectional sofa arranged around a warm fireplace built into a stone wall. Large glass doors provide access to a serene outdoor space, while natural light enhances the wood-beamed ceiling. Decorative elements include woven wall art and a wooden side table.

Cottage in Tiny

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.

FamilyDecorComfort

5.0 out of 5 average rating, 18 reviews

Guest favourite

A geodesic dome is nestled among vibrant fall foliage, showcasing a combination of green coniferous trees and orange and yellow deciduous leaves. The transparent windows of the dome reveal a glimpse of the interior, enhancing the connection to the surrounding nature.

Dome in Utopia

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.

ValueFamilyAccuracy

4.95 out of 5 average rating, 293 reviews

Guest favourite

A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.

Cottage in Tiny

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.

FamilyValueNearby

4.96 out of 5 average rating, 182 reviews

Top guest favourite

A tranquil lakeside view displays a spacious cottage with large windows, reflecting on the calm water. Surrounding trees and a clear blue sky add to the serene atmosphere, inviting relaxation and enjoyment of the natural beauty.

Cottage in Georgian Bay

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.

ValueFamilyBack garden

4.98 out of 5 average rating, 156 reviews

Superhost

Home in Hillsdale

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.

LocationFamilyCleanliness

4.77 out of 5 average rating, 35 reviews

Superhost

A hot tub is situated under a wooden gazebo, featuring railings and a ceiling adorned with decorative elements. Sunlight illuminates the scene, highlighting the inviting water surface. A view of the snowy landscape and frozen lake extends in the background, enhancing the serene atmosphere.

Home in Elmvale

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.

FamilyLocationBack garden

4.85 out of 5 average rating, 113 reviews

Guest favourite

Home in Hillsdale

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.

FamilyValueTV

4.9 out of 5 average rating, 21 reviews

Top guest favourite

A modern bathroom features a freestanding soaking tub situated next to a window, allowing natural light to fill the space. The vanity displays a mirror and toiletries. Nearby, a spacious bed with soft linens is visible, set against a backdrop of wooden walls.

Place to stay in Wasaga Beach

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.

FamilyLocationBiking

5.0 out of 5 average rating, 418 reviews

Top guest favourite

A cozy living area features a spacious sectional sofa adorned with soft pillows, complemented by a minimalist coffee table. Natural elements are highlighted by an accent wall showcasing a scenic forest mural. The nearby sleeping area includes a neatly made bed with fresh linens.

Apartment in Horseshoe Valley

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.

FamilyLocationLayout

4.99 out of 5 average rating, 137 reviews