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

4.84 out of 5 average rating, 148 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.

ValueFamilyOutdoor spaces

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, 54 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

LocationFamilyCheck-in

4.78 out of 5 average rating, 51 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.

ValueFamilyHospitality

4.99 out of 5 average rating, 121 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.

FamilyLocationQuiet

4.91 out of 5 average rating, 104 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!

LocationValueAccuracy

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, 19 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

LocationFamilyAmenities

Apartment in Innisfil

Luxury 2 BR/2Bth@ Friday Harbour

Enjoy staying at the prestigious FH Resort. Friday Harbour wasn’t designed to be a place. It was designed to be a destination. 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- Enjoy All Friday Harbour Has to Offer! .

Hospitality

4.8 out of 5 average rating, 125 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

FamilyValueSkiing

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."

FamilyLocationCheck-in

Apartment in Horseshoe Valley

4.86 out of 5 average rating, 56 reviews

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.

FamilyLocationSleep quality

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.

4.81 out of 5 average rating, 70 reviews

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

LocationValueLong stay

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 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

LocationCleanlinessCheck-in

Private room in Barrie

New place to stay

Double bed with washroom

A cozy sitting area features a white couch draped with a light throw, surrounded by decorative pillows. An antique lamp sits on a small table next to the couch, and a colorful piece of artwork hangs on the wall. Natural light enters through soft curtains.

Private room in Uxbridge

4.6 out of 5 average rating, 5 reviews

small and comfortable

LocationHospitalityWalkability

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

4.93 out of 5 average rating, 198 reviews

4 Bedroom Fully Private Townhouse in Barrie

LocationFamilyTV

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

5 out of 5 average rating, 3 reviews

Nature Lovers Paradise

HospitalityBackyardCleanliness

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

Home in Horseshoe Valley

New place to stay

Simcoe Retreats

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

LocationFamilyCheckout

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

A spacious studio room features a king-size bed adorned with pillows and a cozy blanket. The kitchenette is equipped with wood cabinetry and essential appliances. A dining area with a round table sits near a window, with a comfortable sofa nestled in the corner.

Apartment in Horseshoe Valley

4.67 out of 5 average rating, 3 reviews

Relaxing condo in Shanty Bay Oro

LocationCleanlinessComfort

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, 118 reviews

The Bunkie- A Cozy Modern Escape

LocationValueAccess

4.92 out of 5 average rating, 39 reviews

Home in Uxbridge

10-Acre Country Retreat | Sleeps 10 | Wedding Stay

FamilyLocationBathroom

A cozy bedroom features a double bed adorned with several soft pillows against a calming gray wall. Light filters through sheer curtains, illuminating the space, complemented by a modern bedside lamp. An art piece sits above a small table, adding a personal touch.

Apartment in Barrie

4.67 out of 5 average rating, 3 reviews

Beautiful Modern 2 Bedroom Apt.

LocationFamilyNearby

4.98 out of 5 average rating, 95 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

ValueFamilyQuiet

Apartment in Innisfil

Luxury Sunseeker Stay -New 1BR at Friday Harbour

Hot tubDecorHospitality

Place to stay in Coldwater

4.98 out of 5 average rating, 57 reviews

Woodlands Retreat 2 bdrm Cottage Birders Delight

LocationValueKitchen

Guest suite in Horseshoe Valley

4.93 out of 5 average rating, 15 reviews

King Studio w Kitchenette •Pools•HotTub•Sauna•Spa

ValueLocationTV

Ski-in/ski-out condo rentals

5 out of 5 average rating, 21 reviews

Serenity 2Bed+Sauna+HotTub+Indoor/OutdoorPool

FamilyLocationComfort

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

4.55 out of 5 average rating, 96 reviews

Romantic stay at Friday Harbour

LocationValueSleep quality

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

ValueLocationCondition

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

LocationCheck-inShared spaces

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, 39 reviews

Jacuzzi Suite Relaxing Retreat

FamilyLocationCheck-in

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

LocationFamilyBackyard

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 out of 5 average rating, 10 reviews

Luxurious King Bed Jacuzzi Condo–Pool, Gym, Sauna

FamilyLocationHospitality

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.