Ski-in/Ski-out vacation rentals in Regional Municipality of York

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

Top-rated ski-in/ski-out rentals in Regional Municipality of York

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

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Guest favorite

Home in Barrie

4.86 out of 5 average rating, 93 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.

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

4.75 out of 5 average rating, 68 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, 56 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 favorite

Home in Barrie

5 out of 5 average rating, 7 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!

Condo in Innisfil

4.45 out of 5 average rating, 42 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. Only place to offer exclusive pool & hot tub access at Friday Harbour. Resort offers world-class amenities, including a golf course, marina, and exclusive Beach Club. Just steps from lake, restaurants

Guest favorite

Home in Springwater

4.87 out of 5 average rating, 15 reviews

Cozy Retreat Near Ski Resort - Sleeps 20

Escape to a Cozy Springwater Retreat Discover the charm of our cozy retreat in Springwater Township, located near best ski resorts and Golf club. We welcome small parties and intimate weddings, with additional charges for events. To make your experience even more special, we offer customizable décor packages for occasions like Valentine’s Day, marriage proposals, or birthday parties. Book your stay today and experience the perfect balance of comfort, convenience, and celebration.

Guest favorite

Condo in Innisfil

4.92 out of 5 average rating, 74 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 favorite

Condo in Innisfil

4.96 out of 5 average rating, 73 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."

Guest favorite

Home in Barrie

4.95 out of 5 average rating, 162 reviews

4 Bedroom Fully Private Townhouse in Barrie

This spacious four-bedroom, four-bath townhouse is in Barrie South. It is a fully private and independent house, so you will have full privacy in and out. Enjoy the beautiful lake, which is five minutes away. Guests will have access to a fully stocked kitchen, washer/dryer, free high-speed internet (1500mbps), and a 55" smart TV with popular streaming services. All popular stores and amenities are nearby, within five minutes.

Guest favorite

Apartment in Innisfil

5 out of 5 average rating, 18 reviews

Resort Condo, cozy and modern!

Stunning 2 bedroom condo, located on a beautiful resort with amenities and attractions. 2 Full Bath Condo With Beautiful backyard patio area! Furnished with laundry and wifi on site. Ideal for peace and entertaining inside and outside! Open concept living and kitchen space for dining. Walk to the boardwalk and village. Nature preserve! Restaurants, shopping and more on site!