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

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.

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.

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

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!

Willow Beach Cottage

Welcome to our charming Willow Beach - the perfect place to enjoy Georgina’s best beach, just short walk away. Less than an hour from Toronto, we offer a great getaway from the city. After a day at the beach, you can enjoy a meal on our cedar deck & gaze at the stars. In winter you can go skiing, snowboarding, tubing at The ROC (Recreational Outdoor Campus 3 min drive). We can’t wait to welcome you at our cottage - a true home away from home with everything you need for a perfect stay.

Cozy Retreat Near Golf Club - 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.

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!

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."

Entire Lower Studio

Entirely private lower level studio, not shared and conveniently located apartment. This is only meant for 1-2 days stay not for longterm stays. Designed to fill gaps in booking schedule. → Queen Futon in Living Room → 800ft² / 74m² of total space → Fully Equipped Kitchen! → Smart TV → Outdoor Seating with Fire-pit area! (Summer) → Fast Wifi → Lots of Natural Light with full windows → Very safe neighborhood → Pet Friendly, Fully Fenced