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

Find and book unique ski-in/ski-out homes on Airbnb

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

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

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Guest favorite

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

4.84 out of 5 average rating, 147 reviews

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.

Guest favorite

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.

Apartment in Blue Mountain

4.96 out of 5 average rating, 253 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 (Scheduled to open Fri May 15 2026- Tues Oct 13 2026) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

Top guest favorite

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

4.99 out of 5 average rating, 120 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 favorite

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, 562 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 favorite

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

4.89 out of 5 average rating, 212 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 favorite

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

4.91 out of 5 average rating, 104 reviews

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!

Guest favorite

The cottage features a welcoming exterior framed by a lush canopy of trees. A spacious deck accommodates various seating options, including colorful chairs and a dining table. Large windows provide natural light, reflecting a harmonious connection with the surrounding nature.

Cottage in Algonquin Highlands

4.91 out of 5 average rating, 386 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 favorite

A spacious bedroom is showcased with a large bed dressed in neutral linens and accented by decorative pillows. Natural light enters through a window, illuminating the room's soft gray walls. A contemporary art piece adorns one wall, while a doorway leads to a bathroom.

Townhouse in Blue Mountain

4.91 out of 5 average rating, 140 reviews

Upgraded 3-Bed Chalet in Blue Mtn Village

Licensed with Town of Blue Mountain # LCSTR20220000176 Exquisite and modern three bedroom chalet at Mountain Walk. Right at Blue Mountain Village, ALL LINENS AND TOWELS INCLUDED. Ski hills and golf course. Accommodate up to 7 people and features beautiful kitchen, two and half baths and wood fireplace. Beautifully decorated with tons of upgrades and perfect location this condo offers best of both worlds. kitchen fully equipped! Perfect vacation getaway with all amenities of modern living.

Superhost

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

4.8 out of 5 average rating, 124 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+. Get Some Fun in the Sun and Book Today

Top guest favorite

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.

Apartment in Blue Mountain

4.96 out of 5 average rating, 400 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 (Scheduled to open Fri May 15 2026- Tues Oct 13 2026) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

Guest favorite

An outdoor pool is surrounded by wooden decking, with lounge chairs and umbrellas positioned for shade. The pool deck is enclosed by a low fence, and nearby trees provide a natural backdrop, complementing the condo's architecture.

Townhouse in Blue Mountain

4.86 out of 5 average rating, 227 reviews

Private condo getaway at base of Blue Mountain

Open loft condo at the base of The Blue Mountains, wifi, air conditioning, parking, self check-in, ski-in/out at north chairlift. Sleeps 4 - 5, with 2 full bathrooms, full kitchen with granite counter tops, fireplace, free parking. Seasonal Outdoor pool and year round shared hot tub. 2 min to beaches and village. Surrounded by nature trails. Walk to ski lift. Fun family or getaway retreat with year round activities. Rental License #LCSTR202200000099

Guest favorite

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.

Apartment in Blue Mountain

4.97 out of 5 average rating, 206 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 (Scheduled to open Fri May 15 2026- Tues Oct 13 2026) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)!