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Ski-in/Ski-out holiday rentals in Grey Highlands

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

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Popular amenities for Grey Highlands ski-in/ski-out rentals

Ski-in/ski-out house rentals

Guest favourite
Home in Grand Valley
4.94 out of 5 average rating, 16 reviews

2 bdrm lower level large apt

PatrickRating, 5 stars3 weeks ago
Ich habe 9 Nächte im unteren appartement von Rita verbracht. Rita war immer gut erreichbar und äußerst freundlich. Der checkin hätte einfacher nicht sein können. Die Wohnung war mit allem ausgestattet was ich gebraucht habe. echt super!
Superhost
Home in The Blue Mountains
4.83 out of 5 average rating, 54 reviews

Heated Pool Chalet Near BM Village – Pet Friendly!

CelineRating, 5 stars1 month ago
Our large group had a great time at Tuan's place! From incredibly clear instructions and proactive communication, to the amenities of a heated pool and hot tub, to how close it is to the village and spa, it was a great spot for a weekend away!
Guest favourite
Home in Barrie
4.95 out of 5 average rating, 167 reviews

4 Bedroom Fully Private Townhouse in Barrie

MoniqueRating, 5 stars2 weeks ago
family of 5 adults, one toddler for a weekend. Playground across the street was great. Good location for quick access to major roads. Quiet. Unit was clean & had what we needed for our visit. Great value!
Guest favourite
Home in Barrie
5 out of 5 average rating, 7 reviews

Luxurious and Beautiful, Barrie

MarlonRating, 5 stars4 months ago
Stayed here for the long weekend to do a few activities in the area and have to say that the space was amazing. Would 100% recommend anyone coming to barrie to come stay here!
Guest favourite
Home in The Blue Mountains
4.95 out of 5 average rating, 196 reviews

Pool Open / Serene mountainside home View/Shuttle

TimRating, 5 stars1 month ago
We had a wonderful stay with a family of four including 18 year old teen boys and two dogs. The boys enjoyed the pool table and great tv's while my wife and I enjoyed the great walking and quiet surroundings. It was also easy to have our well trained dogs with us in this location which was wonderful. Thank you Brendan for the terrific stay and allowing us to change our reservation when our plans changed with ease.
Top Guest favourite
Home in Desboro
4.97 out of 5 average rating, 122 reviews

Forest Loft - Forest, Sauna, Ponds & Stargazing

StaceyRating, 5 stars2 months ago
My brother, father and I really enjoyed staying at the loft! Valentine provided us with everything we could have asked for and more. We will definitely be recommending this space to our friends and family :)
Top Guest favourite
Home in Collingwood
4.96 out of 5 average rating, 113 reviews

Driftwood on 6th Heritage Downtown Collingwood

LianneRating, 5 stars2 days ago
I wish this was my house. Truly, that’s my only complaint. The entire place is stunning, but the backyard is a true oasis. The photos don’t even come close to doing it justice. It’s peaceful, beautifully set up, and the kind of space you’ll find yourself daydreaming about long after you leave. Inside, everything was spotless, stylish, and thoughtfully put together. The bed was super comfortable, the location was ideal, and every little detail felt intentional and warm. It’s one of those rare places that feels like home the second you walk in. I already can’t wait to come back. Seema - if you ever decide to sell, please call me first. ❤️
Superhost
Home in Wasaga Beach
5 out of 5 average rating, 4 reviews

Your home away from home

JenniferRating, 5 stars4 months ago
We loved our stay. Such a clean and beautiful space. It had everything we needed and a lot of space for the 9 of us to celebrate my birthday. The hot tub was great after a day of skiing and snowboarding. The host is very responsive too. Amazing overall!

Family-friendly, ski-in/ski-out home rentals

Guest favourite
Cottage in The Blue Mountains
4.92 out of 5 average rating, 13 reviews

Cottage@BlueMountain/Private Beach Access/Hot Tub

TanishaRating, 5 stars2 months ago
We had a great time at the chalet. There was more than enough space for all our 15 guests. Snezhana was extremely helpful, kind and attentive. I would highly recommend staying at any one of Snezhana's stays.
Superhost
Apartment in The Blue Mountains
4.65 out of 5 average rating, 471 reviews

Hidden Gem Escape at Blue Mtn @Great Rates@

SahanaRating, 5 stars1 month ago
We stayed here 2 weekends in a row! It's so close to the mountains. Has great views, and Vijay is super cool It's so convenient getting a place this nice at such a last minut
Guest favourite
Townhouse in The Blue Mountains
4.94 out of 5 average rating, 506 reviews

3BR Sierra Scandi Chic - Closest to Village

SharonRating, 5 stars2 weeks ago
Accommodation was spacious, comfortable, clean and well equipped. Short walk to restaurants, shops and activities. Would recommend!
Superhost
Condo in The Blue Mountains
4.53 out of 5 average rating, 434 reviews

Beautiful Studio Condo in Blue Mountains Sleeps 4

JavierRating, 5 stars4 weeks ago
The place was great. Clean and organized. Everything you need. Good location, quiet, beautiful surroundings. close to Everything.
Superhost
Apartment in The Blue Mountains
4.59 out of 5 average rating, 368 reviews

The Perfect Getaway in Renovated Corner Unit

AlexandraRating, 5 stars2 weeks ago
Veronica’s place was so nice, quiet and a great getaway!
Superhost
Townhouse in The Blue Mountains
4.87 out of 5 average rating, 181 reviews

Private condo getaway at base of Blue Mountain

DhartiRating, 5 stars4 weeks ago
We stayed here over the long weekend and absolutely loved it! The place was gorgeous—cozy, clean, and the view of the mountains from the Airbnb was stunning. The beach just two minutes down the road was also beautiful and made the stay even better. We’ll definitely be booking this place again whenever we return to Blue Mountain!
Guest favourite
Chalet in The Blue Mountains
4.98 out of 5 average rating, 109 reviews

Walk to the village at Blue - Regal

JulieRating, 5 stars4 months ago
Sara’s place was absolutely spectacular! Every little detail was thoughtfully considered, making it perfect for a big group or family. From an abundance of towels, blankets, and dishes to a well-stocked kitchen with spices—you name it, they had it! Our family frequently rents large homes, and it's usually hard to please everyone, but this time, not a single person had any complaints—only praise for how much they enjoyed the stay. The amenities were top-notch! We made great use of the sauna, red light bathrooms, and hot tub. Plus, the home offered plenty of gathering spaces for both adults and kids to relax and enjoy. It was truly a comfortable and welcoming experience. We would absolutely stay here again and highly recommend it to anyone looking for a well-equipped, thoughtfully designed getaway!
Guest favourite
Condo in Blue Mountains
4.92 out of 5 average rating, 344 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

BraydonRating, 5 stars1 week ago
This place was beautiful! As soon as we walked in, we felt at home. All the amenities listed were in the property and in good condition. Richard was very helpful and responsive when we had questions for him. There were extra pillows for people who sleep with more than just one lol. The ceiling fan in the loft really cooled down the place and kept the place at a good temperature. The area is also lovely, with a nearby tennis court on the resort. My friends and I spent most of our time there playing pickleball and tennis. Also, Blue Mountain village is about a 20 minute walk from the resort, so my friends and I went to visit at night. Overall, this was a lovely place to stay for the weekend and I would definitely come back again!

Ski-in/ski-out condo rentals

Superhost
Condo in The Blue Mountains
4.76 out of 5 average rating, 29 reviews

Rustic Studio @ North Creek Resort

AprilRating, 5 stars1 month ago
Loved the place it was beautiful area felt at home. It wasn’t that far from downtown. Teresa and Ian was so helpful with all and any questions I had. I would definitely book it again and definitely recommend it to friends and family.
Guest favourite
Condo in Innisfil
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
Condo in Oro-Medonte
5 out of 5 average rating, 12 reviews

NEW Ski-In Ski-Out 1-BED Condo - Pool, Gym, Sauna

EmilyRating, 5 stars2 months ago
We had a little girls spa weekend. This location fit beautiful as Vetta was a 5 min walk!! The Airbnb had their own little spa, with a sauna, hot tub, pool (inside and outside) and a gym…beautiful amenities! The Airbnb itself was spotless, perfect to dine in (everything you need in a little kitchenette) the little thoughtful snacks were a pleasant surprise! The thoughtful basket in the bathroom “in case you forgot” so helpful and cute! We were 3 girls and it was a perfect amount of space. We would definitely stay here again! And next would go skiing as the ski hill is right there (5-7 minute walk) !! Great location, amazing hosts, great restaurant called the ktchn (very worth it, make a reservation) the best meal I have had in a while! Amazing views!
Guest favourite
Condo in The Blue Mountains
4.8 out of 5 average rating, 203 reviews

Blue Mountain Escape, WIFI, Base of North lift

JessicaRating, 5 stars3 months ago
If you’re looking for a ski in/out location with access to a hot tub and very close to the village action, then this is the place! The unit was clean and tidy, very easy to access, and was exactly as described. We’ll definitely be back!
Top Guest favourite
Condo in Innisfil
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!
Superhost
Condo in Shanty Bay
4.68 out of 5 average rating, 40 reviews

Lux Studio in Horseshoe Valley

LiezelRating, 5 stars2 days ago
Very accommodating and flexible, and they didn’t hesitate to approve our last-minute late check-in request.
Superhost
Condo in The Blue Mountains
4.8 out of 5 average rating, 220 reviews

Mountainside Retreat - Ski in/out - Endless Coffee

DianaRating, 5 stars3 weeks ago
My friends and I went to the spa for a girls night and we stayed here. It was a great time and everything worked out so well. The instructions were clear and everything was perfectly clean! Overall, great place to stay and we are thinking on making it our monthly stay for when we go to the spa!
Guest favourite
Condo in Oro
4.84 out of 5 average rating, 87 reviews

Spacious King Studio - Pool, Hottub, Kitchenette

DanRating, 5 stars3 weeks ago
Our stay was exactly what we were looking for quiet, nice location, good price communication was clear and concise. If we are ever that way again we would definitely stay here again. Would be nice to stay more than one night to enjoy the area and what the location has to fully offer.

Quick stats about holiday rentals that are ski-in ski-out in Grey Highlands

  • Total rentals

    280 properties

  • Nightly prices starting at

    $66 NZD before taxes and fees

  • Total number of reviews

    29K reviews

  • Family-friendly rentals

    180 properties are a good fit for families

  • Pet-friendly rentals

    90 properties allow pets

  • Rentals with a pool

    150 properties have a pool

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Grey County
  5. Grey Highlands
  6. Ski-in/ski-out rentals