Ski-in/Ski-out holiday rentals in Innisfil

4.87 out of 5 average rating, 128 reviews

An A-frame house featuring a white exterior and a steep roof stands beside a serene lake. A gravel driveway leads to the entrance, surrounded by greenery. Large windows allow ample natural light, providing views of the lake and trees in the background.

Home in Little Lake

Lakefront detached house on the little lake

♥️an unique, lovely elf house in front of the little lake. Here you’ll find a unique hideaway in the middle of the city Barrie with gorgeous lake views as far as the eye can see. ♥️ Only one hour drive from Toronto. Walking distance to everywhere (shoppers,restaurants, cinemas….) ♥️This home including new furniture, microwave, coffee maker, washing machine and all other appliances ! Walk out the back door and be greeted by our updated dock where you can fish for pike, perch, pickerel and bass.

An aerial view captures the expansive layout of Friday Harbour, showcasing various buildings along the marina and natural surroundings. A peaceful golf course is visible with a distinctive lighthouse, all framed by serene water reflections under a twilight sky.

4.9 out of 5 average rating, 90 reviews

Family-friendly luxury getaway at Friday Harbour

IT IS HALLOWEEN TIME! At Canada's most sought after all seasons resort, you, your family, and friends can unwind to the peaceful serenity of Lake Simcoe, spend hours in the 200-acre Nature Preserve, experience unforgettable fine dining, or stroll along the beautiful boardwalk. Our one-of-kind 2-bedroom open concept luxury Corner unit with floor-to-ceiling windows will give you a taste of paradise - an hour away from the Greater Toronto Area! Come and enjoy all that Friday Harbour has to offer!

4.83 out of 5 average rating, 113 reviews

A spacious living area features a comfortable tan sofa and modern black dining chairs surrounding a circular table. A gas fireplace and television are positioned against a light stone wall, while large windows allow natural light to fill the room. Decorative elements include a floor plant and a wine display.

Townhouse in Shanty Bay

Ravine Backyard, King Bed, Jacuzzi, Pool, Hot Tub

Forget your worries in this spacious and serene space at Highland Estates. You get a full designer suite perfect for couples, equipped with a King Sized Bed, and a Jacuzzi for romantics. Prepare your own meals in the fully equipped kitchen with Microwave and Electric Stove. Access your favorite Streaming-TV accounts like Netflix, Prime, and Disney+ Close to Vetta Spa and major Ski Hills; literally the Best Retreat in Oro-Medonte. Book with Us Today! Please note the Fireplace isn't working.

4.99 out of 5 average rating, 114 reviews

An open concept living area features rustic wood beams and sliding barn doors. Comfortable wicker chairs are paired with a wooden coffee table, while a cozy sofa adds to the inviting space. The modern kitchen is visible in the background, creating a seamless flow.

Guest house in Mansfield

Brookside Cottage - Charming Rural Getaway Mulmur

Our cozy guest house, situated in the Headwaters region, has it all! Close to hiking,golfing,biking,skiing. XCski/snowshoe from your door! Big skies for astronomers and astrophotography! We offer 32 acres of forest and fields for walking and taking in the magnificent views. The area boasts fine restaurants, boutiques, markets and artisans. Minutes to Mono Cliffs, Boyne, Mansfield Ski Club and easy driving to Blue Mountain and Wasaga Beach. Ideal for couples, solo adventurers or a small family.

5 out of 5 average rating, 11 reviews

A welcoming living area is highlighted by comfortable seating arrangements, including a sofa and two armchairs. A round coffee table sits in the center, surrounded by a soft area rug. A mounted television is above a modern fireplace, with natural light filtering through the windows.

Home in Barrie

Luxurious and Beautiful, Barrie

Welcome to our cozy retreat in Barrie, Ontario, just a short walk from the beautiful waterfront and popular beaches. Our home is perfect for a relaxing getaway or an adventurous weekend, offering modern amenities, a fully equipped kitchen, and a spacious outdoor patio in a quiet, family-friendly neighborhood. Our retreat offers year-round appeal, with activities like beach days in summer and skiing in winter. With free parking and easy access, we’re excited to host your unforgettable stay!

4.9 out of 5 average rating, 84 reviews

The exterior of a three-story building exhibits a yellow facade with white accents and balconies. A central staircase leads to the entrance, flanked by well-maintained shrubs and grass. The pathway is paved, creating a welcoming approach to the property.

Flat in oro- medonte

Oro-medonte/in/out pool/ski-2

relax with the whole family at this peaceful Highland Estate (Carriage hills )at 90 highland dr, Oro-medonte, ont, L0L 2X0! A beautiful resort with recreation activities for everyone. Outdoor / insdoor swimming pool, public bbq, hiking and mountain biking. Its located near Horse and Mount st louis Moonstone ski resorts. Also nearby is the Vetta nordic Spa and a beautiful golf resort. 2 min walk to the pool Close to Centennial park- barrie Couchiching Beach-orrila Treetop trekking!!

4.81 out of 5 average rating, 21 reviews

Home in Angus

The Angus Nest

Enjoy this bright and open space that features a master suite with a jacuzzi, cozy family room with a fireplace, and a fully equipped kitchen with modern appliances, and laundry room. Stay entertained with high-speed internet and a smart TV, and take advantage of the spacious deck. Four parking spots available extra spot if needed. Whether you're planning a family vacation, a ski trip, or a peaceful retreat, our home is the perfect place to relax and unwind. Book your stay today!

The marina at twilight features calm waters reflecting the vibrant colors of the sunset. Multiple boats are docked along the well-lit marina, with modern buildings lining the shore, creating a serene and inviting atmosphere.

4.94 out of 5 average rating, 88 reviews

Luxury Getaway @ Friday Harbour Condo at Marina

Book your accommodations with us & enjoy the prestigious FH Resort. FH wasn’t designed to be a place. It was designed to be a destination. Were you can unwind, disconnect & reconnect all your senses with the healing powers of the forest & beautiful sunsets, truly feel relaxed. Whether you come to take in the peaceful serenity of the lake, spend hours in the Nature Preserve or mingle with friends over a gourmet meal, there’s no shortage of ways to enjoy your days."

Place to stay in Oro Station

A serene winter landscape is depicted with the sun shining through bare trees. Snow blankets the ground, creating a tranquil atmosphere, while long shadows from the trees stretch across the snow-covered forest floor.

4.96 out of 5 average rating, 104 reviews

The Bunkie- A Cozy Modern Escape

Our cozy, modern Bunkie is nestled in a secluded forest setting with access to local trails and attractions. Whether you are seeking relaxation, adventure or exploration - this beautiful, four season destination will not disappoint. The bunkie has ski in ski out/ ride in ride out access to the Trails at Hardwood Ski and Bike for those who are interested. Trail passes are required, and available at a discount when staying at the bunkie. Contact us for more info.

5 out of 5 average rating, 12 reviews

The exterior of a spacious cottage is displayed, surrounded by lush green grass and trees. Large windows provide ample natural light to the interior, while a stone pathway leads to the entrance. The multi-level structure features a red roof and earthy stone accents.

Cottage in Utopia

Simcoe Cottage + Hot Tub + Sauna + Private Retreat

Welcome to your own private cottage situated on 3 acres of beautiful woodlands, where comfort and relaxation awaits! This massive custom-built cottage is the perfect setting for large families or travelling friends. Our tastefully furnished oasis boasts one of a kind décor, with plenty of room for indoor and outdoor activities. All accompanied with private access to the Nottawasaga River. Only 1hr from Greater Toronto Area.

4.93 out of 5 average rating, 184 reviews

A cozy living area features an orange L-shaped sofa adorned with decorative pillows, paired with a round coffee table. A 55" smart TV sits on a sleek black stand against the wall, surrounded by neutral decor and natural light from the nearby window.

Home in Barrie

4 Bedroom Fully Private Townhouse in Barrie

This spacious four-bedroom, four-bath townhouse is in Barrie South. It is a fully private and independent house, so you will have full privacy in and out. Enjoy the beautiful lake, which is five minutes away. Guests will have access to a fully stocked kitchen, washer/dryer, free high-speed internet (1500mbps), and a 55" smart TV with popular streaming services. All popular stores and amenities are nearby, within five minutes.

The bedroom displays a king-sized bed adorned with soft linens and multiple decorative pillows. Next to the bed, a stylish lamp provides warm light, while three framed nature photos hang above the headboard. A cozy seating area features a plush sofa with decorative cushions and a small table, enhancing comfort.

4.95 out of 5 average rating, 20 reviews

Serenity 1Bed+Sauna+HotTub+Indoor/OutdoorPool

Welcome to our modern zen retreat in Horseshoe Valley—perfect for families or friends looking to relax, explore, and make lasting memories. Just 2 hours from Toronto, our condo offers a prime location to experience it all. Minutes away from the Vettä Nordic spa, skiing, mountain biking, golf, tree-top trekking and more. Created with tranquility in mind, our space is the perfect place to return to after a day of adventure.

Popular amenities for Innisfil ski-in/out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/out house rentals

A spacious outdoor deck provides a comfortable lounge area, featuring a sectional sofa, colorful accent chairs, and a dining table. A large yellow umbrella offers shade, while views of the private dock and calm waters create a serene setting for relaxation.

Home in Innisfil

4.72 out of 5 average rating, 69 reviews

Luxurious Lake front Island Townhome, Innisfil, ON

4.53 out of 5 average rating, 51 reviews

Home in Gilford

Beautiful House by Lake Simcoe

A comfortable living room features a light-colored sectional sofa with a decorative pillow. Natural light filters through the window, which is covered with sleek shades. French doors are visible, leading to another space, and a framed artwork is positioned on the floor.

Home in Wasaga Beach

Peaceful house at the Beach

4.92 out of 5 average rating, 25 reviews

An aerial view of Olive & Willow Lodge reveals a spacious green lawn surrounded by trees. The white house is centrally located, with a driveway leading to the entrance. Scenic highways are visible along the property's edge, enhancing the natural tranquility of the setting.

Home in Uxbridge

Cozy 3-Bdrm Lodge beside Dagmar & Lakeridge Resort

The entrance of the home features a wide staircase leading to double front doors, framed by elegant columns. Two black chairs are positioned on the porch, accompanied by warm outdoor lighting. A garage is visible on the left, showcasing brick detailing along the facade.

Home in Springwater

4.75 out of 5 average rating, 8 reviews

3 bedroom 4 bathroom escape

A dark-clad chalet features large windows that provide natural light. In the foreground, three red Adirondack chairs are arranged on a grassy area, surrounded by a stone pathway and a small shrub, creating a relaxed outdoor space.

Home in Mansfield

4.55 out of 5 average rating, 20 reviews

Peace and Quiet at our Vacation home

Home in Georgina

New place to stay

Luxury 5BR Retreat in Heart of Keswick

An exterior view of the modern farmhouse showcases a sloped roof and a prominent red door. Sturdy wooden steps lead up to a private deck, surrounded by trees and greenery, creating a connection to the natural surroundings.

Home in Mansfield

The Sheds: 2 BR Coach House Apmt

Family-friendly, ski-in/out home rentals

A bright bedroom features a spacious bed with blue linens and a modern ceiling fan. A desk is positioned nearby, while large sliding glass doors open to a view of the backyard, allowing natural light to enter the room.

Private room in Barrie

4.6 out of 5 average rating, 10 reviews

Bright room! Free parking

A stunning view features a bright sunset behind an industrial building along a tranquil body of water. The vibrant orange and golden hues reflect on the surface, creating a serene atmosphere. Silhouettes of trees and distant structures outline the scene, enhancing the natural beauty.

Home in Collingwood

Dream vacation in Georgian Bay Collingwood, ON (2)

4.95 out of 5 average rating, 76 reviews

A spacious living area is shown, featuring a large sectional sofa adorned with decorative pillows. A round wooden coffee table sits at the center, accompanied by a cozy throw blanket. The open kitchen area is visible in the background, illuminated by recessed lighting.

Home in Whitby

Entire Brand new 3 bedroom house

Flat in Barrie

New place to stay

Stylish Downtown Barrie Condo

Flat in Whitby

1 Bed, Bath & Kitchen Basement Available Monthly

Flat in Innisfil

Luxury 2 BR/2Bth@ Friday Harbour

5 out of 5 average rating, 5 reviews

The exterior of a spacious two-story home is displayed, featuring a bricked facade and a welcoming entrance. Parking spaces are visible for multiple vehicles, with decorative planters hanging by the door. Large windows allow for ample natural light, enhancing the overall curb appeal.

Private room in Uxbridge

Country Inn-Like RetreatTrail Views Explore 240 km

4.95 out of 5 average rating, 128 reviews

Home in Collingwood

Driftwood on 6th Heritage Downtown Collingwood

Ski-in/out apartment rentals

5 out of 5 average rating, 3 reviews

Serenity 2Bed+Sauna+HotTub+Indoor/OutdoorPool

5 out of 5 average rating, 15 reviews

A cozy bedroom is presented with a spacious bed adorned in crisp white linens and a dark throw blanket. Flanking the bed are two bedside lamps, adding soft illumination. A plant adds a touch of greenery, while a living area is visible through an open doorway.

Apartment in Oro-Medonte

NEW Ski-In Ski-Out 1-BED Condo - Pool, Gym, Sauna

The living area is furnished with a light sofa and an accent chair, accompanied by a circular coffee table on a patterned rug. Large windows provide natural light and views of the outdoors. A modern kitchenette showcases sleek cabinetry and an island with seating.

4.45 out of 5 average rating, 71 reviews

Romantic stay at Friday Harbour

A spacious studio features a king-size bed with premium bedding, adjacent to a stylish sectional couch. Natural light pours in through large windows, illuminating the open floor plan. A dining table is positioned nearby, providing a comfortable area for meals.

4.67 out of 5 average rating, 57 reviews

Lux Studio in Horseshoe Valley

A sandy beach area features several wooden picnic tables shaded by blue umbrellas, overlooking a calm body of water. In the background, a modern building with a blue roof houses outdoor seating along the waterfront, surrounded by a vibrant landscape.

4.77 out of 5 average rating, 31 reviews

Luxury 2 BR Condo at FH All Season Resort

A serene swimming pool is framed by a modern building with large glass windows. Surrounding trees exhibit vibrant autumn colors, enhancing the tranquil outdoor setting. A small diving board is visible at the shallow end, while a ladder provides access to the pool.

4.75 out of 5 average rating, 4 reviews

Lux 2BD Apartment in Horseshoe Valley, Oro-Medonte

A two-story building features a red and white facade, with covered balconies and white railings. A path leads toward the entrance, flanked by grass. The exterior is illuminated, ensuring visibility at dusk.

Private room in Oro-medonte

4.58 out of 5 average rating, 12 reviews

Margarita Vacation Getaway 2

An open-concept living area features a cozy gas fireplace surrounded by stone, offering a relaxed seating arrangement. A large TV is mounted above the fireplace. The space transitions to a dining area with modern fixtures, while soft natural light filters in through windows.