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

4.86 out of 5 average rating, 139 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.

Apartment in Horseshoe Valley

4.75 out of 5 average rating, 28 reviews

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.

Guesthouse 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.

4.91 out of 5 average rating, 101 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.

Condo in Innisfil

Family-friendly luxury getaway at Friday Harbour

Happy Holidays! 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!

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.

5 out of 5 average rating, 18 reviews

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.

4.86 out of 5 average rating, 29 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!

Townhouse in Horseshoe Valley

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.

4.84 out of 5 average rating, 126 reviews

Ravine Backyard, King Bed, Pool, Fun and Sun

Forget your worries in this spacious and serene space at Highland! A designer suite perfect for couples, equipped with a King Sized Bed, and a Jacuzzi for romantics. Fix your own meals in the kitchen with Microwave and Electric Stove. Access your favorite Streaming-TV accounts like Netflix, Prime, and Disney+ Take your sweetie to Vetta Spa, and lots of activities in the area; literally the Best Retreat in Oro-Medonte. Book with Us Today! Please note there is no dishwasher.

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.

4.68 out of 5 average rating, 76 reviews

Lux Studio in Horseshoe Valley

Forget your worries in this spacious and Tranquil Studio condo with king bed & premium mattress. Walking distance to ski slopes . Wall mounted smart TV, and optional room divider for maximum privacy. This unit can sleep 4. The stylish sectional can be converted to increase additional sleeping for 2 more guests . This corner unit condo boasts additional windows with no units above. You will be nestled in Horseshoe Valleys serene, and inviting space for ultimate relaxation."

Guest suite in Horseshoe Valley

5 out of 5 average rating, 12 reviews

Romantic King Studio•Pools•HotTub•Sauna•Spa•Gym

Welcome to “Snug In” — Your Peaceful Escape. Located in the heart of Horseshoe Valley, you’ll be minutes from top destinations including Horseshoe Valley Resort, Horseshoe Ski Resort, and The Heights Ski & Country Club. Enjoy year-round activities such as skiing, biking, scenic hiking trails, treetop adventures, spa experiences, fitness studios, local dining, and boutique services. Wasaga Beach, supermarkets, and everyday essentials are all within easy reach.

The living room features a cozy arrangement with a gas fireplace and a wall-mounted TV. A coffee table sits centrally on a colorful area rug, surrounded by comfortable seating options including a sofa and two armchairs. Natural light fills the space through large windows.

4.91 out of 5 average rating, 32 reviews

Country Retreat in Horseshoe Valley with 2 bdrs

Escape to this beautiful 2-bedroom, 4-bed condo nestled in Horseshoe Valley. Experience the indoor/outdoor pool, outdoor gas fire pit, 2-person jacuzzi, and indoor fireplace. Close to Horseshoe Resort, Vetta Spa, Hiking & Biking Trails & more. Whether seeking adventure or relaxation, this condo ensures an unforgettable experience. Recently renovated, this well-appointed vacation retreat is perfect for the whole family or group of friends.

4.93 out of 5 average rating, 192 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/ski-out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/ski-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, 74 reviews

Luxurious Lake front Island Townhome, Innisfil, ON

5 out of 5 average rating, 15 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

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

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

4.91 out of 5 average rating, 32 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

Private & Serene 10-Acre Willow Retreat

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

4 out of 5 average rating, 4 reviews

Luxury 5BR Retreat in Heart of Keswick

5 out of 5 average rating, 3 reviews

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/ski-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

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

Cabin in Bracebridge

New place to stay

111 Acre Woodland Retreat - Hot Tub & Sauna

Apartment in Barrie

Stylish Downtown Barrie Condo

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/RV in Wasaga Beach

Beach camp trailer

A door stands framed by a welcoming garden, featuring vibrant red flowers and lush greenery. A large sign marked 'First Aid' is prominently displayed above the entrance, with planters hanging to the sides. The area exudes a sense of care and accessibility.

Barn in Mansfield

Mulmur Adventures Penthouse

5 out of 5 average rating, 7 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

Apartment in Innisfil

Luxury Sunseeker Stay -New 1BR at Friday Harbour

Ski-in/ski-out condo rentals

5 out of 5 average rating, 19 reviews

Serenity 2Bed+Sauna+HotTub+Indoor/OutdoorPool

4.93 out of 5 average rating, 92 reviews

Condo in Innisfil

Luxury Getaway | Friday Harbour Condo

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.

Condo in Innisfil

4.49 out of 5 average rating, 79 reviews

Romantic stay at Friday Harbour

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.

4.94 out of 5 average rating, 35 reviews

Serenity Studio Sauna+HotTub+Indoor/OutdoorPool

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 Horseshoe Valley

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.

4.31 out of 5 average rating, 32 reviews

Jacuzzi Suite Relaxing Retreat

An open-concept living area is showcased featuring a cozy gas fireplace framed by a stone wall. A large TV is mounted above it. A dining table with several wooden chairs is visible, alongside a comfortable armchair and coffee table.

4.78 out of 5 average rating, 63 reviews

Carriage Country Club Home Away From Home

A spacious bedroom is highlighted by a king-size bed with a plush white comforter. Two round mirrors adorn the black accent wall, reflecting natural light from the window. A soft tan throw blanket and decorative pillows complement the bed, alongside a bedside table and a green potted plant.