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

4.87 out of 5 average rating, 150 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, historically, 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 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 and bass.

FamilyLocationAccuracy

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, 57 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

LocationFamilyBathroom

4.79 out of 5 average rating, 52 reviews

A spacious open-concept living area features large windows allowing natural light to fill the room. A wood-burning stove is positioned against a stone fire surround. Modern white furniture, including two armchairs, complements the wooden dining table with multiple chairs, enhancing the inviting atmosphere.

Cottage in Bala

Granite Ridge - Bala-Lake Muskoka-Gravenhurst

Bala - Lake Muskoka dream, insect less. Two living rooms, dock, paddle boat, sand bottom beach Lake Muskoka. Parking, unlimited wifi, 3 bedroom plus loft & 3 bathrooms, laundry. Woodstove, and 3 fireplaces . Open concept with 2 large living area. Propane gas stove, microwave, dishwasher, barbeque, outdoor teak dining table, fire pit, Muskoka chairs. Three bedrooms with 6 beds, & pull out couch, loft. New mattresses, couches, and appliances. Visit Santa's village (31km), Discovery Museum.

ValueFamilyHiking

4.99 out of 5 average rating, 122 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.

LocationFamilyPets

4.92 out of 5 average rating, 107 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!

LocationFamilyParking

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, 90 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."

FamilyLocationComfort

4.8 out of 5 average rating, 126 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 Horseshoe Valley

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+. Get Some Fun in the Sun and Book Today

ValueFamilyAmenities

Apartment in Horseshoe Valley

Two King & Queen Beds, Hot Tub, Pool, BBQ

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!

4.94 out of 5 average rating, 93 reviews

Condo in Innisfil

Luxury Getaway | Friday Harbour Condo

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."

ValueLocationBiking

Apartment in Horseshoe Valley

King Bed Suite | Pool • Hot Tub • Gym Access

Escape to comfort in this bright King Bed Suite just 1.5 hrs north of Toronto. Perfect for a peaceful getaway, ski adventure, or spa retreat, this resort stay blends comfort and convenience. Enjoy the pool, hot tub, gym, and clubhouse, with golf courses, ski hills, hiking trails, and the world-class Vetta Nordic Spa nearby. Relax on your private balcony, cozy up on the pull-out couch, or stream shows with fast Wi-Fi.

ValueFamilyWalkability

4.8 out of 5 average rating, 60 reviews

Cottage in Victoria Harbour

A year-round Jacuzzi hot tub is situated on a stone patio, surrounded by lush green grass and tall trees. A planter with vibrant flowers adds a touch of color nearby, creating a serene outdoor relaxation space.

Perfect summer gateway.lots to do here

Discover your perfect summer escape at our fully renovated, private lakefront cottage on Georgian Bay in Victoria Harbour, less than 2 hours from the GTA. Enjoy breathtaking sunrise views, a cozy fire pit, BBQ, and a fun-filled game room with a pool table. Relax year-round in the hot tub under the stars. LCBO and Foodland are just 5 minutes away, and outdoor activities like biking and kayaking are right at your doorstep

FamilyValueHospitality

4.82 out of 5 average rating, 71 reviews

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.

5.0 out of 5 average rating, 11 reviews

Luxurious King Bed Jacuzzi Condo–Pool, Gym, Sauna

Welcome to the Highland Estate Private Condominiums! Nestled on the scenic rolling hills of Horseshoe Valley, this brand-new, ski-in/ski-out one-bedroom condo is the perfect retreat for adventure seekers and relaxation lovers alike. Whether you’re hitting the slopes, exploring hiking trails, or unwinding in the jacuzzi, this property offers the ultimate blend of luxury, comfort, and convenience.

LocationFamilySkiing

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 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

LocationFamilyCheck-in

4.93 out of 5 average rating, 198 reviews

A spacious home is surrounded by lush greenery, featuring a well-maintained driveway leading to the entrance. Lounge chairs are placed on the patio, and the landscape includes manicured gardens. The architecture displays a combination of traditional and modern elements with multiple windows letting in natural light.

Home in Shanty Bay

Nature Lovers Paradise

ComfortCleanlinessHospitality

5.0 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

LocationHospitalityCheck-in

4.83 out of 5 average rating, 6 reviews

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

Peace and Quiet at our Vacation home

FamilyLocationComfort

4.55 out of 5 average rating, 20 reviews

Home in Tiny

Cozy home

New place to stay

Home in Wasaga Beach

Pearl Cozy Beach House-4 Seasons

WalkabilityAccuracyBeach

Home in Georgian Bay

New Cottage Town at Marina & Pool!

LocationAmenitiesHospitality

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

Indoor spaces

Family-friendly, ski-in/ski-out home rentals

4.93 out of 5 average rating, 40 reviews

Home in Uxbridge

10-Acre Country Retreat | Sleeps 10 | Wedding Stay

FamilyLocationHeating

Apartment in Innisfil

Luxury 2 BR/2Bth@ Friday Harbour

Hospitality

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.

The Bunkie- A Cozy Modern Escape

LocationValueKitchen

4.96 out of 5 average rating, 118 reviews

An open-plan living space showcases a modern kitchen with stainless steel appliances and a sleek island. The dining area features a dark table surrounded by chairs. The comfortable seating area includes a neutral sofa and accent chairs. Natural light fills the room through large windows.

Apartment in Horseshoe Valley

Lower Level LuxSuite - 1min Walk from Heated Pool!

FamilyValueDecor

4.57 out of 5 average rating, 21 reviews

Place to stay in Coldwater

A cozy outdoor seating area features two chairs with colorful cushions, positioned beside a gas grill. Flowering plants, including white blooms and purple coneflowers, adorn the gravel pathway leading to the straw bale cottage, enhancing the natural setting.

Woodlands Retreat 1 bdrm Cottage *Birders Delight*

LocationValueView

5.0 out of 5 average rating, 85 reviews

A private outdoor space features a refreshing swimming pool surrounded by a wooden deck. Comfortable lounge chairs and umbrellas provide shaded seating areas. Lush greenery and colorful flowers line the perimeter, while a large glass door offers a view into the connected indoor living space.

Cottage in Oro Station

Oro Lakeshore Rustic Cottage Salt Water Pool

LocationFamilyHot tub

4.67 out of 5 average rating, 12 reviews

4.98 out of 5 average rating, 97 reviews

The exterior of the loft features a covered deck with a bistro set and railings, accessed by a staircase. The entrance is beneath the deck, with a white door and a potted plant hanging nearby. The building's siding is a light grey, surrounded by greenery.

Loft in Midland

Season's Retreat

FamilyLocationNearby

Decorative cushions with tropical leaf patterns are positioned on a neatly made bed with crisp white linens. The arrangement highlights a serene sleeping area, focusing on comfort and a relaxed ambiance.

Apartment in Barrie

1 Bedroom Full Private Apartment

LocationHeatingHospitality

5.0 out of 5 average rating, 5 reviews

Ski-in/ski-out condo rentals

A modern kitchen features dark wood cabinetry and granite countertops. Essential appliances include a microwave, refrigerator, and oven. The counter is equipped with a coffee maker and various utensils, while a sink is positioned to the right. Soft lighting enhances the workspace.

4.89 out of 5 average rating, 119 reviews

Lovely condo unit in Horseshoe Valley

LocationValueNearby

The living area features a cozy gas fireplace surrounded by a light stone facade, complemented by comfortable seating. A circular glass table is accompanied by four chairs, and a modern television is mounted on the wall. The open layout connects the living space to the kitchen.

4.57 out of 5 average rating, 79 reviews

Lower Level Jacuzzi Suite @ Carriage Hills

FamilyValueNearby

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.

4.77 out of 5 average rating, 65 reviews

Carriage Country Club Home Away From Home

ValueFamilyHiking

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

Romantic stay at Friday Harbour

LocationValueWifi

4.55 out of 5 average rating, 98 reviews

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.

4.33 out of 5 average rating, 40 reviews

Jacuzzi Suite Relaxing Retreat

LocationFamilyPool

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

Margarita Vacation Getaway 2

LocationWifiGetting around

4.58 out of 5 average rating, 12 reviews

A spacious room features a king-size bed adorned with a leaf-patterned duvet. A comfortable seating area includes a sofa, a wooden coffee table, and a dining table with four chairs, while large windows invite natural light.

4.85 out of 5 average rating, 98 reviews

Country Retreat Horseshoe Valley

LocationFamilyLaundry