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

NelsonRating, 5 stars53 months ago

Brand New Luxury 1 Bedroom Condo at Friday Harbour

We had a great time at Maurizio’s place. The communication was super easy and quick and the place looks exactly like it does on the pictures. The neighborhood is very conveniently located and although it’s a lively neighborhood the apartment is very quiet! Would absolutely recommend to stay there!

4.92 out of 5 average rating, 76 reviews

Family-friendly luxury getaway at Friday Harbour

ChristopherRating, 5 stars1 week ago

A quiet week long retreat which was topped off by this comfortable and beautiful spot in Friday Harbour. Check in and out was incredibly simple, bonus of free underground parking and so many amenities both in the rental and nearby at the marina. a perfect week. Highly recommend and hope to be back for a future stay!

Top guest favourite

4.96 out of 5 average rating, 75 reviews

Luxury Getaway @ Friday Harbour Condo at Marina

AngelaRating, 5 stars3 weeks ago

We had such a peaceful long weekend stay at Ana's! The location was perfect and exactly described; overlooks right into the marina, amazing restaurants just right down the steps and extremely quiet! We didn't hear a single sound from any of neighbours around us. The space looked even more beautiful than the pictures. My husband and I were shocked to see just how incredibly clean the apartment was; not a single speckle anywhere! We were welcomed by a lovely snack basket (which my husband devoured on the first night) and a bottle of wine. Even included amenities in the bathroom which was wonderful since I forgot our toothbrush. The bathroom was so cozy and such a lovely surprise to have a tub. We will definitely be coming back!

4.87 out of 5 average rating, 103 reviews

Home in Barrie

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.

Top guest favourite

Home in Willow Beach

5 out of 5 average rating, 5 reviews

Willow Beach Cottage

Welcome to our charming Willow Beach cottage - 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.

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.

Home in Innisfil

4.74 out of 5 average rating, 58 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

5 out of 5 average rating, 7 reviews

Home in Barrie

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!

4.87 out of 5 average rating, 15 reviews

Home in Springwater

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.

5 out of 5 average rating, 7 reviews

Flat in Innisfil

Family-friendly 1 bedroom Apt

Welcome to our cozy, newly renovated, one bedroom vacation retreat in Friday Harbour, designed with your friends and families’ comfort in mind! The home is equipped with highspeed internet, open concept fully equipped kitchen and a living area with Fire Smart TV (Netflix, Amazon Prime, etc) perfect for gatherings. High countertop table or cozy convertible coffee table to enjoy your meals. Good nights’ rest guaranteed with hybrid mattresses and extra pillows.

Flat in Barrie

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

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Popular amenities for Regional Municipality of York ski-in/out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/out house rentals

Private room in Shanty Bay

5 out of 5 average rating, 14 reviews

Couples Luxury Getaway

JanetRating, 5 stars4 days ago

a beautifully quiet, spacious location with wildlife in the backyard to enjoy while lounging on the backyard patio. the room was clean and we were the only guests so we had exclusive use of a large guest washroom. Gilles made us a delicious fresh French crepe breakfast that topped off the visit, we could have eaten those all day, but alas the cycling trail was calling and we had to answer. Jennifer and Gilles were very welcoming hosts and gave us privacy as needed. if you're cycling the simcoe loop trail this is a great place to stay, it's right on the trail!

4.56 out of 5 average rating, 9 reviews

Bright room! Free parking

YangRating, 5 stars7 months ago

Thank you for the hassle-free check in and convenient place for us to stay! Paul is very responsive and patient 💗

3.92 out of 5 average rating, 12 reviews

Basement Sweet nest

DakotaRating, 5 stars8 months ago

Very nice. Clean, quiet. And Paul was very fast at responding! Very good

TinaRating, 5 stars12 months ago

lovely room!

I would definitely stay here again. very quiet and spacious. I will recommend this place to my friends.

3.57 out of 5 average rating, 7 reviews

Basement Love Nest

NatalieRating, 5 stars9 months ago

Other then being cold which was fixed by the host great little place to stay

4.17 out of 5 average rating, 6 reviews

Great view，high internet

ArslanRating, 5 stars5 months ago

Great place for a one night stamd.

KaidianRating, 5 stars9 months ago

Lovely room

I had no issues staying at Paul's place, I'd recommend if you're ever in Barrie.

3.78 out of 5 average rating, 9 reviews

Basement sweet room

Omaid AhmadRating, 5 stars9 months ago

This Airbnb stay was cozy and comfortable, just like home. Everything was clean and welcoming. A great choice for a peaceful stay!

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Ski-in/out apartment rentals

4.92 out of 5 average rating, 76 reviews

Family-friendly luxury getaway at Friday Harbour

ChristopherRating, 5 stars1 week ago

A quiet week long retreat which was topped off by this comfortable and beautiful spot in Friday Harbour. Check in and out was incredibly simple, bonus of free underground parking and so many amenities both in the rental and nearby at the marina. a perfect week. Highly recommend and hope to be back for a future stay!

NelsonRating, 5 stars53 months ago

Brand New Luxury 1 Bedroom Condo at Friday Harbour

We had a great time at Maurizio’s place. The communication was super easy and quick and the place looks exactly like it does on the pictures. The neighborhood is very conveniently located and although it’s a lively neighborhood the apartment is very quiet! Would absolutely recommend to stay there!

Top guest favourite

4.96 out of 5 average rating, 75 reviews

Luxury Getaway @ Friday Harbour Condo at Marina

AngelaRating, 5 stars3 weeks ago

We had such a peaceful long weekend stay at Ana's! The location was perfect and exactly described; overlooks right into the marina, amazing restaurants just right down the steps and extremely quiet! We didn't hear a single sound from any of neighbours around us. The space looked even more beautiful than the pictures. My husband and I were shocked to see just how incredibly clean the apartment was; not a single speckle anywhere! We were welcomed by a lovely snack basket (which my husband devoured on the first night) and a bottle of wine. Even included amenities in the bathroom which was wonderful since I forgot our toothbrush. The bathroom was so cozy and such a lovely surprise to have a tub. We will definitely be coming back!