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

4.86 out of 5 average rating, 146 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.

LocationFamilyDecor

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.

FamilyLocationAir conditioning

4.99 out of 5 average rating, 120 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.

LocationFamilySleep quality

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!

LocationValueSleep quality

4.8 out of 5 average rating, 123 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

FamilyValueBathroom

Apartment in Horseshoe Valley

4.8 out of 5 average rating, 88 reviews

Pet Friendly, 2 King Beds, Gym, Pool

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!

FamilyLocationParking

5 out of 5 average rating, 27 reviews

Apartment in Innisfil

Relaxing 2BR Escape @ FH | Fire Pit & Pets Welcome

Welcome to our spacious, newly renovated, two bedroom vacation retreat in Friday Harbour, designed with your friends and families’ comfort in mind! The home is equipped with highspeed internet, open concept fully equipped kitchen and a living area with 65" QLED Smart TV (Netflix, Amazon Prime, etc) perfect for gatherings. High countertop table or cozy convertible coffee table to enjoy your meals. Good nights’ rest guaranteed with hybrid mattress and extra pillows.

LocationFamilyComfort

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.

4.99 out of 5 average rating, 67 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.

ValueFamilyAccuracy

Apartment in Horseshoe Valley

4.89 out of 5 average rating, 55 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.

ValueFamilyAmenities

Cottage in Victoria Harbour

A year-round Jacuzzi hot tub sits near the edge of the property, featuring a smooth surface and built-in jets. In the background, a fire pit is surrounded by blue Adirondack chairs, with kayaks lined up on the grass and the expansive waterfront visible.

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

FamilyValueAmenities

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

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.

LocationCheckoutComfort

4.95 out of 5 average rating, 78 reviews

A fully renovated cottage is surrounded by greenery, featuring large windows that allow for ample natural light. The outdoor area includes a wide deck with seating, a fire pit, and a pergola. A wooden dock extends into the lake, providing access for water activities.

Home in Uxbridge

Lakeside Lodge Scott’s Vacation House Rules (Reno)

🌲 As Seen on Scott’s Vacation House Rules (2025!) 🌲 Welcome to Uxbridge Lakeside Lodge – Where Luxury Meets Nature Completely renovated by Scott McGillivray’s expert team, this spectacular retreat has been professionally designed to blend luxury vibes with a warm country lodge feel. Featured on Scott’s Vacation House Rules 2025, this is not just a getaway — it’s a destination.

FamilyLocationAccess

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

LocationHospitalityQuiet

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

LocationAmenitiesWalkability

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

LocationValueAmenities

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

CleanlinessHospitalityBreakfast

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

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

LocationFamilyRiver

Home in Georgian Bay

New Cottage Town at Marina & Pool!

LocationAmenitiesHospitality

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

LocationCleanlinessHospitality

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

ValueLocationCheck-in

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.

5 out of 5 average rating, 85 reviews

Woodlands Retreat 1 bdrm Cottage *Birders Delight*

FamilyLocationDecor

4.92 out of 5 average rating, 38 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

LocationFamilyAccuracy

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.

LocationFamilyAccuracy

4.98 out of 5 average rating, 93 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

LocationValueBeach

Apartment in Innisfil

Luxury 2 BR/2Bth@ Friday Harbour

Hospitality

Guest suite in Horseshoe Valley

4.93 out of 5 average rating, 15 reviews

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

ValueFamilySleep quality

Ski-in/ski-out condo rentals

5 out of 5 average rating, 21 reviews

Serenity 2Bed+Sauna+HotTub+Indoor/OutdoorPool

LocationFamilyQuiet

4.94 out of 5 average rating, 93 reviews

Condo in Innisfil

Luxury Getaway | Friday Harbour Condo

FamilyLocationAccuracy

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, 95 reviews

Romantic stay at Friday Harbour

LocationValueBeach

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, 91 reviews

Lux Studio in Horseshoe Valley

LocationFamilySolo travel

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, 52 reviews

Serenity Studio Sauna+HotTub+Indoor/OutdoorPool

LocationFamilyAir conditioning

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

LocationHot tubShared 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

FamilyLocationAmenities

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.