Ski-in/Ski-out holiday rentals in Oro-Medonte

4.85 out of 5 average rating, 133 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.

A cozy bedroom is highlighted by a plush bed adorned with soft linens and decorative pillows. A bedside lamp casts a warm glow, while art prints with nature motifs hang above the bed. Nearby, a modern dresser and a comfortable sofa are visible, providing inviting spaces for relaxation.

4.96 out of 5 average rating, 27 reviews

Serenity Studio Sauna+HotTub+Indoor/OutdoorPool

Welcome to our modern zen studio retreat in Horseshoe Valley—perfect for couples or smaller groups of 4 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. *Please note this is a studio condo with a kitchenette

5 out of 5 average rating, 15 reviews

Flat in Shanty Bay

Luxury Jacuzzi Suite w/ Full Kitchen & Heated Pool

Welcome to your all-season retreat. A beautifully designed luxury suite offering comfort, privacy and amenities in Horseshoe Valley. Surrounded by rolling hills, forests and scenic trails, this property provides the perfect balance between relaxation & recreation. Guests have access to a year-round heated pool, hot tub, sauna, fitness room, playground & outdoor fire pit lounge. Perfect for a romantic escape, family getaway or weekend adventure, every detail is designed for an unforgettable stay.

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.

Cottage in Victoria Harbour

4.86 out of 5 average rating, 56 reviews

20 min to Mount St. Louis ski resort.private&Cozy

Discover Our intimate home where You have access to the entire property. fully renovated , well equipped situated on the very southern point of Georgian bay in Victoria Harbour,Our lake front cottage is Less than 2 hours drive from the GTA . Delight in expansive waterfront views, mesmerizing sunrise ,a fire pit, BBQ, Pool table , game room and a year-round Jacuzzi Hot Tub. LCBO & Foodland 5 minutes away Also Take advantage of plenty outdoor activities such as bike riding And kayaking

5 out of 5 average rating, 18 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

Welcome to Highland Estate Private Condominiums, where modern comfort meets the beauty of the great outdoors. Nestled at the top of Horseshoe Valley Resort (just a 3-minute walk to the top of Horseshoe Hill), this cozy and stylish condo is perfect for: • Skiers & Snowboarders craving direct access to slopes • Sports Enthusiasts seeking golf, hiking, mountain biking, and more • Families looking for an active and relaxing getaway • Couples seeking a romantic retreat with serene surroundings

Place to stay in Cold wate

4.82 out of 5 average rating, 28 reviews

Amazing Cottage in Horseshoe Valley

Kick back and relax in this calm, stylish and spacious three bedroom cottage. Its a perfect getaway outside Toronto for the families who want to spend their time to relax and enjoy the activities around the Horseshoe area just 1.5 Hrs drive from Toronto. Enjoy your stay in this cozy and unique decorated cottage in the middle of a prestigious neighbourhood. This place is 5 minutes to Horseshoe resort and close to hiking trails, ski resorts, snowmobile trails and mountain biking terrain.

4.83 out of 5 average rating, 71 reviews

A row of charming units features gabled roofs and inviting porches, framed by colorful trees and well-maintained landscaping. The path leads towards the units, which are complemented by lush lawns and seasonal foliage.

Flat in Shanty Bay

Gym+Pool+PetFriendly+KingBeds

Located just about 1.5 hours North of Toronto, this is the place you'll want to be. In an area where most units are similar, what makes this property unique is all the extra things we add to ensure you'll taken care of. Whether you aim to ski, hit golf at one of eighteen golf courses, mountain bike or hike in several landscape trails, soak in the healing experience of Vetta Nordic spa, or simply relax at the tranquility of the area, this place is simply yours to enjoy!

4.85 out of 5 average rating, 109 reviews

A bright and spacious living area features a comfortable white sofa paired with dark blue accent chairs. A stylish dining table is set for meals, while a gas fireplace and mounted television create a cozy atmosphere. Natural light fills the room through large windows.

Home in Shanty Bay

King Bed, Pool, Gym, Ravine View, Your Getaway!

Enjoy a stylish experience in this spacious and serene space at Highland Estates Resort. You get a completely equipped designer suite that is perfect for couples sneaking away, or families looking for the perfect vacation. Enjoy a peaceful night in your private Jacuzzi then snuggle up in a King Bed. The next day, prepare your own meal in the fully equipped kitchen with Microwave and Electric Stove. Access Netflix, Prime, Disney+. Our Pool is Open! Book Us Today

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, 114 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, 16 reviews

A large custom-built cottage is set against a snowy landscape, surrounded by tall trees. A Canadian flag is visible near the entrance, complementing the stone pathway leading to the home. The property features a screen-in porch and multiple windows reflecting the winter light.

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, 188 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.

Popular amenities for Oro-Medonte ski-in/out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/out house rentals

4.74 out of 5 average rating, 72 reviews

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

Luxurious Lake front Island Townhome, Innisfil, ON

Home in Georgina

4.5 out of 5 average rating, 6 reviews

Cozy 2 bedroom ice fishing&skiing

5 out of 5 average rating, 12 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

Home in Gilford

4.56 out of 5 average rating, 54 reviews

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

4.77 out of 5 average rating, 13 reviews

An open living area features a high wooden ceiling with large angled windows allowing natural light to fill the space. A stone fireplace serves as a focal point, complemented by a dark leather sectional sofa and a coffee table. A plush armchair adds extra seating.

Home in Collingwood

Charming Chalet in Collingwood

4.9 out of 5 average rating, 29 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

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

Family-friendly, ski-in/out home rentals

The spacious master bedroom is furnished with a queen bed, a desk and chair, and a dresser. Natural light filters through a window adorned with plaid curtains. A neutral color palette enhances the room's tranquil atmosphere.

Private room in Barrie

Bright Master Bedroom+Private B

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

4.97 out of 5 average rating, 32 reviews

A spacious bed is positioned in a well-lit room, featuring a flat-screen TV mounted on the wall. Large sliding glass doors offer a view of Lake Simcoe, leading to an outdoor space with seating. Natural light fills the room, creating a serene ambiance.

Private room in Gilford

Waterfront Room with private bathroom

Three snowmobiles are seen traveling along a snow-covered trail surrounded by tall, bare trees. The path is flanked by dense foliage, creating a natural corridor. Snow is kicked up from the tracks, highlighting the winter recreational activity.

Home in Shanty Bay

Nature Lovers Paradise

The kitchen features modern white cabinetry and sleek stainless steel appliances, including a refrigerator, stove, and dishwasher. Ample counter space is provided, and large windows allow natural light to brighten the area. A neutral tile floor complements the contemporary design.

Home in Innisfil

Cozy bungalow on Yonge st

A designated outdoor gathering area features a circular arrangement of colorful plastic chairs in blue, red, and turquoise. A fire pit is centered on a stone surface, with a stack of firewood nearby. Sunlight brightens the space, creating a relaxed atmosphere.

Camper van/Motorhome in Wasaga Beach

Beach camp trailer

Private room in Sutton

4.67 out of 5 average rating, 3 reviews

A holiday resort with air, gardens, river, nature.

Flat in Innisfil

Luxury 2 BR/2Bth@ Friday Harbour

Ski-in/out apartment rentals

4.57 out of 5 average rating, 14 reviews

King Suite – heated Pool, Sauna & Kitchen

4.91 out of 5 average rating, 95 reviews

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.

Apartment in Innisfil

Family-friendly luxury getaway at Friday Harbour

5 out of 5 average rating, 12 reviews

Serenity 2Bed+Sauna+HotTub+Indoor/OutdoorPool

4.94 out of 5 average rating, 90 reviews

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.

Apartment in Innisfil

Luxury Getaway @ Friday Harbour Condo at Marina

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.

Apartment in Innisfil

4.47 out of 5 average rating, 76 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.

4.69 out of 5 average rating, 65 reviews

Lux Studio in Horseshoe Valley

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.