Ski-in/Ski-out holiday rentals in York Region

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

Top-rated ski-in/ski-out rentals in York Region

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

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Guest favourite

Home in Barrie

4.87 out of 5 average rating, 117 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.

Condo in Innisfil

4.77 out of 5 average rating, 31 reviews

Luxury 2 BR Condo at FH All Season Resort

Enjoy staying at prestigious FH Resort Community with a wide range of winter activities. Experience a beautiful winter wonderland, whether is running through the snow on the trails Nature Preserved, cross country skiing, or Strap on your skates for a quick game in the staking ring. Want to Skip: Snow Valley Ski Resort or Horseshoe Resort Horseshoe are 30 min away. ** For Pool & Beach access home owner card purchase available for a separate $400 fee, photo ID and one week notification required.

Cottage in Oro Station

4.57 out of 5 average rating, 7 reviews

Oro Lakeshore Rustic Cottage Salt Water Pool

Escape to your year-round retreat in the heart of Oro-Medonte, where serenity meets adventure. Whether you're drawn to the snow-covered slopes or the sun-drenched landscapes, this charming cottage offers the perfect sanctuary for all seasons. Our spacious cottage is an ideal haven for ski enthusiasts, just moments away from the region's renowned slopes. In the summer, explore nearby attractions such as beautiful hiking trails, pristine lakes for swimming and fishing, or indulge in water sports.

Condo in Innisfil

4.76 out of 5 average rating, 78 reviews

Hottub#Pool#Firepit#QueenBed

Unwind with your family at this serene getaway. The condo is fully equipped, including a fully stocked kitchen, a queen bed, and a sofa bed. The pool is available to use during the summer months, while the hot tub is open year-round, unless closed for maintenance by resort management, which is beyond our control. We do have a few negative reviews, so please take a moment to read our responses before making your decision. We would be delighted to host you at our charming and peaceful property.

Home in Innisfil

4.73 out of 5 average rating, 66 reviews

Luxurious Lake front Island Townhome, Innisfil, ON

This luxurious 3 storey vacation home is located in the beautiful Friday Harbour Resort, in Innisfil, ON. The town home has been upgraded with state of the art appliances for the residents comfort. It is a corner unit, with Glass stair case. The resort itself has a variety of resources to keep everyone entertained during their stay. This includes access to a golf club, hiking, canoeing, kayaking, tennis, basketball and more. Along with the physical activities, there are also relaxing options

Guest favourite

Home in Barrie

5 out of 5 average rating, 10 reviews

Luxurious and Beautiful, Barrie

Welcome to our cozy retreat in Barrie, Ontario, just a short walk from the beautiful waterfront and popular beaches. Our home is perfect for a relaxing getaway or an adventurous weekend, offering modern amenities, a fully equipped kitchen, and a spacious outdoor patio in a quiet, family-friendly neighborhood. Our retreat offers year-round appeal, with activities like beach days in summer and skiing in winter. With free parking and easy access, we’re excited to host your unforgettable stay!

Apartment in Barrie

The Affordable Private Barrie Apartment

Come stay in our spacious, entirely private and conveniently located apartment. I prefer hosting families, business travellers and mature groups. The neighbourhood is quiet, the unit is located in a lower level of a side-split home. → 1 large Bedrooms → 800ft² / 74m² of space → Fully Equipped Kitchen! → Smart TV → Outdoor Seating with Fire-pit area! → Fast Wifi → Designated Work Area → Lots of Natural Light with full windows → Very safe neighborhood → Pet Friendly, Fully Fenced in

Home in Springwater

4.33 out of 5 average rating, 3 reviews

3 bedroom 4 bathroom escape

Step into comfort, style, and tranquility in our brand-new, beautifully designed home - the perfect place to unwind, explore, and create lasting memories. From the moment you walk in, you'll notice the thoughtful touches: modern architecture, sunlit open spaces, and a fresh, clean atmosphere that only a newly built home can offer. Whether you're planning a quiet retreat or a lively getaway with family and friends, this space was built with relaxation and connection in mind.

Guest favourite

Condo in Innisfil

4.89 out of 5 average rating, 82 reviews

Family-friendly luxury getaway at Friday Harbour

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!

Top Guest favourite

Condo in Innisfil

4.96 out of 5 average rating, 82 reviews

Luxury Getaway @ Friday Harbour Condo at Marina

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."

Condo in Innisfil

4.4 out of 5 average rating, 58 reviews

Romantic stay at Friday Harbour

Lakeside luxury at Friday Harbour Resort in Town of Innisfil. Steps from Lake Simcoe, offers upscale comfort and resort-style amenities. Enjoy a gourmet kitchen, spacious bedroom, and a large wrap-around balcony with panoramic forest views. Modern conveniences include in-unit washer/dryer. The Resort offers world-class amenities, including a golf course, marina, and exclusive Beach Club. Just steps from lake and restaurants!

Private room in Barrie

4.56 out of 5 average rating, 9 reviews

Bright room! Free parking

The house is new renovation, new painting and furnitures are all new. The house have bathroom, working place ,shared kitchen , High Speed Internet , Free Parking, Near Bus Stop, Plaza just cross the street, 7 minutes to Cineplex Cinema, LA Fitness, Zehrs, LCBO , 5 minutes to College and Hospital, 7 Downtown, 800 meters to Beach , 500 meters to GAS Station and Tim Horton and more , 20 minutes to Horseshoe Valley or Snow Valley