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Ski-in/Ski-out holiday rentals in Lake Simcoe

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Top-rated ski-in/out rentals in Lake Simcoe

Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

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Guest favourite
An open layout of the studio unit is displayed, featuring a modern kitchen with a breakfast bar and sleek cabinetry. The cozy living area contains a pullout sofa with decorative cushions, and a spacious king bed is situated in the corner, complemented by subtle green accent walls.
Flat in The Blue Mountains
4.97 out of 5 average rating, 213 reviews

Evergreen Studio-KingBed/Pool/HotTub/Shuttle

Renovated studio unit at the North Creek Resort featuring: * King Bed * SMART TV, High-Speed Rogers Ignite WIFI and TV * Pull Out Sofa * Stone Fireplace * Modern, Stylish Decor *please note there is not a traditional oven- there is a microwave/convection oven combo along with a stove top *Shuttle Service *Year Round Hot Tub *Pool (closed for the winter season- to reopen Spring '26) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

Top guest favourite
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
4.99 out of 5 average rating, 114 reviews

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.

Guest favourite
A tree house is nestled among tall trees, featuring a wooden structure with a balcony and staircase. Soft sunlight filters through the branches, highlighting the natural wood finish and the serene forest surroundings.
Treehouse in Port Perry
4.98 out of 5 average rating, 557 reviews

Treehouse on private, isolated forest (300 acres)

You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.

Guest favourite
The lodge-style cabin is nestled among snow-covered trees, showcasing a combination of dark and red wood exterior. A spacious deck extends from the entrance, featuring a hot tub and outdoor seating. Snow blankets the ground, creating a serene winter landscape.
Chalet in Dysart et al
4.88 out of 5 average rating, 208 reviews

Dingle Run Lodge (ski-in/ski-out) at Sir Sam's

SKI-IN/SKI-OUT Lodge style cabin in a 2 acre forest directly on Sir Sam's Ski & Bike. Enjoy the ease of ski-in/ski-out, snow shoeing, hiking or biking right from the beautiful deck which over looks an 8-person hot tub, 20' sauna and a unique firepit. In the summer take a short walk to Eagle Lake public beach and boat launch for fishing/swimming. Endless adventures near by like the Haliburton Forest, dog sledding, wolf center and so much more! EV fast charging station available for our guest!

Guest favourite
Cottage in Algonquin Highlands
4.91 out of 5 average rating, 377 reviews

Long Beach on Big Boshkung

Welcome to Long Beach on Boshkung. A beautiful private 2 bedroom (2 Queens) , 1 Loft (2 Singles) cottage complete with a 3 piece bathroom on 300 feet of frontage on Big Boshkung Lake in Haliburton Ontario. Bungalow cottage property is a unique combination of comfort and beauty. Shaded by towering white pines, the cottage holds one of the best and clearest views of Boshkung lake, private 300 foot sand beach and spectacular sunsets. Front deck on lake side has hill may not be child friendly

Guest favourite
The studio features a spacious living area with a comfortable sofa and a modern armchair. A king bed adorned with blue and yellow linens is positioned in the background. Natural light filters through the window treatments, enhancing the serene ambiance.
Apartment in The Blue Mountains
4.83 out of 5 average rating, 451 reviews

Ski in/out @ North Creek W King bed! New Hot Tub

Welcome to our beautiful studio at the foot of Blue Mountain ski hills. Fully renovated from top to bottom in 2021 and ready for visitors! 'Cascade Cabin' is a modern studio which sleeps 3 and features a King bed with a queen sofa bed in the living area. Unit features a fully equipped kitchen with seating for 3, full bathroom with shower & new soaker tub. The condo is located within minutes from Blue Mountain Village and within walking distance to the north ski lift.

Guest favourite
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
4.85 out of 5 average rating, 110 reviews

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

Top guest favourite
A tranquil scene is depicted, showcasing a small cabin surrounded by vibrant autumn foliage. Lush grass and wetland plants frame the calm waters, reflecting the colorful trees in the background, creating a serene natural environment.
Farm stay in Kawartha Lakes
4.85 out of 5 average rating, 119 reviews

GcLittle Tourist Cabin on the Marsh

Nature enthusiasts welcome. We offer a large campsite complete with dock on a private nature reserve. Stay in a converted/restored century tourist cabin/hunt camp on the edge of Provincially Significant Wetlands & Woodlands and overlook 5 pristine acres of wetlands off the Pigeon River in the heart of the Kawarthas. All this is set on a 55 acre organic farm. We have a 10 kw solar panel, native plant nursery as well as heritage breed cattle, turkeys and chickens.

Guest favourite
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.
Place to stay in Oro Station
4.96 out of 5 average rating, 115 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.

Top guest favourite
The airy studio unit features a spacious king bed framed by green accent walls. A cozy sectional sofa is positioned in front of a coffee table. Natural light filters through window shutters, highlighting the adjacent balcony with Muskoka chairs.
Flat in The Blue Mountains
4.96 out of 5 average rating, 361 reviews

Studio at Blue-KingBed/Pool/HotTub/Shuttle

Welcome to our studio unit in the mountainside North Creek Resort! *King bed *sofa bed-double sized memory foam mattress *SMART TV, High-Speed Rogers Ignite WIFI and TV *Cookware, Utensils and Keurig *freshly painted *remodeled washroom Property Features: *Shuttle Service *Year Round Hot Tub *Pool (closed for the winter season- to reopen Spring '26) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

Top guest favourite
An open-concept studio unit is shown, featuring a cozy living area with a dark sectional sofa and a wooden coffee table. The king bed is visible in the background, accompanied by modern bedding. The kitchen area includes a bar with stools and is equipped with countertop appliances.
Flat in The Blue Mountains
4.97 out of 5 average rating, 159 reviews

Alpine Bliss: King Bed/Pool/HotTub/Shuttle

Newly renovated studio unit at the mountainside North Creek Resort featuring: * King Bed * SMART TV, High-Speed Rogers Ignite WIFI and TV * Double Pull Out Sofa * Remodeled Washroom *Equipped Kitchen with Keurig * Modern, Stylish Decor *Shuttle Service *Year Round Hot Tub *Pool (closed for the winter season- to reopen Spring '26) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)!

Top guest favourite
A modern cabin is nestled among tall trees, showcasing large floor-to-ceiling windows that invite natural light. A spacious covered porch, framed by lush greenery, features outdoor seating. The grassy area surrounding the cabin adds to the serene atmosphere of the wooded retreat.
Home in Eagle Lake
4.97 out of 5 average rating, 115 reviews

HyggeHaus—sleek snuggly secluded apres-ski cabin

For a getaway that merges serenity with style; imagination with intention, look no further than HyggeHaus and its private Haliburton Highlands wooded retreat. Indulge in a stay where there is time and space for both leisure and adventure, and where beautiful design enables beautiful experiences. To view a short property video, search Youtube for "HyggeHaus Eagle Lake Haliburton". STR Licence# STR-25-00010

Popular amenities for Lake Simcoe ski-in/out rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Ski-in/out house rentals

Superhost
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
4.74 out of 5 average rating, 72 reviews

Luxurious Lake front Island Townhome, Innisfil, ON

Guest favourite
Home in The Blue Mountains
4.89 out of 5 average rating, 266 reviews

Large 4 Br - 4.5 Bathroom: 2 King beds/Sauna/games

Superhost
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, 188 reviews

4 Bedroom Fully Private Townhouse in Barrie

Guest favourite
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
5 out of 5 average rating, 12 reviews

Luxurious and Beautiful, Barrie

Guest favourite
A master bedroom features a spacious bed adorned with a blue and white comforter. Light wooden flooring is complemented by a decorative nightstand and a stylish chandelier. Large windows allow natural light to fill the room, offering views of the greenery outside.
Home in The Blue Mountains
4.94 out of 5 average rating, 232 reviews

Serene mountainside home with View/Shuttle Bus

Guest favourite
The exterior of the town-home is showcased, featuring a combination of stone and blue siding. Neatly manicured lawns surround the property, and several large windows allow natural light to illuminate the interior. A small tree is planted in the foreground, adding a touch of greenery.
Home in The Blue Mountains
4.85 out of 5 average rating, 117 reviews

Blue Mountain Village Townhome 4 Bedroom w Shuttle

Guest favourite
A modern bathroom is equipped with a walk-in shower featuring marble-like tiles. A wall-mounted mirror reflects soft light from three globe fixtures above a large sink, complemented by grey cabinetry. Two neatly hung towels are visible, and a small rug adds warmth to the floor.
Home in Brampton
4.75 out of 5 average rating, 123 reviews

Brand new One Bedroom apartment

Top guest favourite
Home in Collingwood
4.95 out of 5 average rating, 140 reviews

Driftwood on 6th Heritage Downtown Collingwood

Family-friendly, ski-in/out home rentals

Guest favourite
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
4.91 out of 5 average rating, 96 reviews

Family-friendly luxury getaway at Friday Harbour

Top guest favourite
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
4.94 out of 5 average rating, 90 reviews

Luxury Getaway @ Friday Harbour Condo at Marina

Guest favourite
A dining area features a long wooden table surrounded by six chairs, with vibrant red cushions. A vase is placed at the center of the table, and sunlight streams through a large window, illuminating the room and offering a view of the greenery outside.
Cottage in Oro Station
4.86 out of 5 average rating, 64 reviews

Farmhouse next to Bike, Hike, Ski Forest Trails

Guest favourite
The exterior of a Victorian farmhouse is displayed, featuring a metal roof and rustic wooden siding. A spacious deck is visible, surrounded by vibrant flower beds and green lawn. Seating areas include patio furniture and a fire pit, offering a welcoming outdoor space.
Chalet in Mulmur
4.79 out of 5 average rating, 53 reviews

The Sheds: Victorian Farmhouse 5BR Ski-In Ski-Out

Top guest favourite
The dock is illuminated by string lights, creating a warm ambiance. Multiple lounge chairs surround a central seating area, positioned under trees. Kayaks and paddleboards rest against the side, with water reflecting their vibrant colors and the soft glow of the lights.
Cottage in Kawartha Lakes
4.98 out of 5 average rating, 89 reviews

Beautiful Balsam Lake Retreat-2Hammocks on Balsam

Guest favourite
Place to stay in Cold wate
4.82 out of 5 average rating, 28 reviews

Amazing Cottage in Horseshoe Valley

Guest favourite
Apartment in The Blue Mountains
4.92 out of 5 average rating, 50 reviews

Open Loft Condo at Blue Mountain

Guest favourite
Cottage in Victoria Harbour
4.86 out of 5 average rating, 58 reviews

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

Ski-in/out apartment rentals

Guest favourite
The open concept living area features a spacious sofa with blue accent pillows, a flat-screen TV mounted above a modern fireplace, and large windows providing natural light. A dining area with bar stools is visible, complemented by a rustic wooden table.
Apartment in The Blue Mountains
4.82 out of 5 average rating, 214 reviews

Blue Escape | Ski-In-Out, Hot Tub & Shuttle

Superhost
A cozy sleeping area features a spacious bed with a patterned blanket and two bedside lamps mounted on a black headboard. Artwork is displayed on the gray walls, and a nightstand is positioned beside the bed, complementing the warm wood flooring.
Apartment in The Blue Mountains
4.77 out of 5 average rating, 338 reviews

Blueview Suite (Studio Condo) Blue Mountain

Superhost
A modern dining area features a large wooden table surrounded by six upholstered chairs. Above, a geometric light fixture provides illumination, while artwork hangs on the wall, complementing the warm tones of the cabinetry visible in the kitchen.
Apartment in The Blue Mountains
4.88 out of 5 average rating, 198 reviews

Close to Village, 2 Bedrooms , Rivergrass

Superhost
The kitchen displays modern appliances, including a refrigerator, microwave, and stove, set against a stylish backsplash. A granite countertop extends into a small dining area with two black stools, while light fixtures offer bright illumination in the space.
Apartment in The Blue Mountains
4.81 out of 5 average rating, 215 reviews

Blue Mountain Escape, WIFI, Base of North lift

Guest favourite
Apartment in The Blue Mountains
4.89 out of 5 average rating, 509 reviews

Explore a Winter Wonderland at Blue Mountain

Top guest favourite
A modern living area is featured, showcasing a grey sofa and two armchairs. A coffee table sits in front of the seating arrangement, and a wall-mounted television is positioned above a linear fireplace. Natural light streams through large windows, illuminating the space.
Apartment in Blue Mountains
4.93 out of 5 average rating, 394 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

Superhost
A cozy living area features a dark sofa and a pull-out couch, complemented by colorful throw pillows. Natural light streams through multiple windows, highlighting the light wood flooring. A large flat-screen TV is mounted above a black fireplace, and a door leads out to a patio area.
Apartment in The Blue Mountains
4.84 out of 5 average rating, 459 reviews

Mountain Side One Bedroom

Guest favourite
A heated hot tub is situated outdoors, surrounded by a snow-covered landscape. The tub features bubbling water and is framed by tall trees, with nearby townhouses visible beyond a protective fence.
Apartment in The Blue Mountains
4.83 out of 5 average rating, 201 reviews

Rivergrass Hot Tub, Pool, Clean, Lovely, Great Loc

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