Chalet holiday rentals in Grey Highlands

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Popular amenities for Grey Highlands chalet rentals

Family-friendly chalet rentals

Superhost
Chalet in The Blue Mountains
4.8 out of 5 average rating, 194 reviews

Chalet At Blue - Private chalet with hot tub

JamieRating, 5 stars3 months ago
Great communication with Shawn from start to finish, the home was what we expected and equipped with almost everything we needed. Lots of parking available, great spaces for groups to hang out, easy to host team meals. We were there for a ski trip and got pounded with snow, burying all sidewalks and making the walk to villages and chairlifts more difficult - but doable.
Guest favourite
Chalet in The Blue Mountains
4.9 out of 5 average rating, 82 reviews

Stylish Log Chalet w/ Hot tub Minutes to Village

RachelRating, 5 stars1 month ago
Tamara’s rental was perfect for a girls weekend! Great sleeping arrangements. Hot tub was nice and clean. The whole canine was spot less and clean. Only 10 min uber ride into blue mountain. Great location. Would definitely recommend staying here.
Chalet in Markdale
4.77 out of 5 average rating, 57 reviews

Authentic Tyrolean Chalet at base of BVSC

ShwetaRating, 5 stars8 months ago
The place was really nice and we enjoyed with our family! We would love to visit again!!
Chalet in Craigleith
4.86 out of 5 average rating, 14 reviews

The Aqua Villa

GurleenRating, 5 stars57 months ago
Beautiful chalet on the water. Lovely views! Close to blue mountain village. Spacious. Abeer stays in the chalet beside this one but we felt we had more than enough privacy!
Guest favourite
Chalet in The Blue Mountains
4.83 out of 5 average rating, 171 reviews

Octagon Chalet fire pit, close to theVillage

MayaRating, 5 stars3 months ago
We had a great stay at Vivian's place! The chalet was very clean, exactly as described, and fit our group of 13 comfortably. We especially liked the big dining table that was great for meals and games together, and that the kitchen/living room area was on a separate floor from all the bedrooms as this made it easy to accommodate different schedules within the group. One thing to note is that the kitchen didn't have some cooking items like tin foil, cooking oil, and a baking sheet, so be sure to bring those if you'll need them. There was coffee however which we really appreciated! Vivian was very responsive to all messages and sent clear instructions for the space. Definitely recommend for a big group trip, would book again!
Chalet in The Blue Mountains
4.77 out of 5 average rating, 225 reviews

-BBQ-Full Kitchen-W/D-Sauna-Backyard-Parking-A/C

AnkatRating, 5 stars1 week ago
very nice and easy to communicate owners. the place is easy to find, accurate description. and most important, the place is safe specially for the kids. will definitely choose this place again.
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!
Superhost
Chalet in Kimberley
4.76 out of 5 average rating, 17 reviews

Beaver Valley family chalet with a view

KristiRating, 5 stars3 months ago
Great value, only 10 minutes from Beaver Valley Ski Club, quiet and safe neighbourhood, great space and rooms!

Luxury chalet rentals

Guest favourite
Chalet in The Blue Mountains
4.96 out of 5 average rating, 24 reviews

The Four Leaf Clover at The Blue Mountains for 12

EmmaRating, 5 stars3 months ago
Enjoyed our stay very much! It was the perfect place to host our 11 person bachelorette. It had all the amenities and was walkable to the village (20min). It was a close drive to collingwood as well! Host was responsive and helpful - overall a great stay for us!!
Superhost
Chalet in The Blue Mountains
4.77 out of 5 average rating, 92 reviews

Retreat at Blue with private Hot Tub

AhmadRating, 5 stars6 days ago
Ira is amazing! Very fast to respond and communicate. Place is amazingly clean. Just 2 reminders to the next visitors: hut tob is private, just it has some visibility from some neighbors, which was ok for us. So, it was alright. Secondly, by law, fire place is not allowed. Thank you so much Ira. Wonderful job.
Superhost
Chalet in The Blue Mountains
4.8 out of 5 average rating, 89 reviews

Starlight Mountain House: Chalet w Hot Tub + Games

PatriciaRating, 5 stars1 week ago
Our group of 12 women were very well accommodated in this chalet for our spa weekend. The number of bedrooms, beds, and bathrooms was perfect. The size of the unit allowed for everyone to have their own space. The layout allowed for us to gather as a group of 12 or breakout into smaller groups . The chalet was clean, the kitchen was well equipped with utensils, dishes , barware etc. There was more than adequate seating in the living areas and at the dining table/island. Location was fabulous- minutes to Scandinave Spa, walking distance to Village and easy drive to Thornbury and Collingwood for shopping, dining and takeout. A wonderful weekend getaway.
Guest favourite
Chalet in The Blue Mountains
4.89 out of 5 average rating, 142 reviews

1 Lake/Ski Luxury Chalet /HOT TUB

ElizabethRating, 5 stars3 weeks ago
I had about 15-20 people coming to a get together for my wedding, everything was clean and well prepared. Even though it rained it was still a very pleasant time at the hot tub.
Guest favourite
Chalet in The Blue Mountains
4.9 out of 5 average rating, 39 reviews

Shale Beach House - 5mins to Blue Mtn Village!

LaurelRating, 5 stars1 month ago
We had a lovely stay. The kitchen had everything we needed to cook and bake. All rooms were neat and clean. The linens were lovely, right down to the comfortable pillows. Every bedroom was decorated and comfortable as the next. The house has amazing natural light. The house is a close car ride to restaurants, shopping and hiking. We were a group of four and we all agreed that we would return.
Superhost
Chalet in The Blue Mountains
4.9 out of 5 average rating, 48 reviews

The Green Moose Classic Chalet w/ Hot Tub, BBQ, La

KatiaRating, 5 stars4 weeks ago
We stayed for two nights and had a great time! The location was perfect — close to everything we needed. Tony was a wonderful host, very friendly and responsive. Highly recommended!
Guest favourite
Chalet in Meaford
4.9 out of 5 average rating, 63 reviews

UrbanChalet: Secluded 20Acres W/Pizza Oven+Firepit

NiñaRating, 5 stars1 month ago
Me and 9 girlfriends had a blast celebrating my best friend’s Bachelorette party here! Oksana was helpful and responsive, despite having a very busy day of her own, and being proactive in letting us know beforehand when to expect a response from her/giving us an alternative for quicker communication. The space was clean, perfect for the amount of guests, and the already-supplied firewood was a great bonus. Would recommend both home and host!
Superhost
Chalet in The Blue Mountains
4.8 out of 5 average rating, 25 reviews

Lake/Ski chalet with HOT TUB/SAUNA!

KanwalRating, 5 stars1 day ago
It was great to stay Elena and Vlad’s property. They both were very helpful and great hosts. Cottage was super clean and pristine.

Lakefront chalet rentals

Top Guest favourite
Chalet in Meaford
4.98 out of 5 average rating, 87 reviews

Sundance of Blantyre Lodge w Hot Tub, Sauna & Pond

SabinaRating, 5 stars2 weeks ago
We thoroughly enjoyed our stay. The place was beautiful and exactly as described. Michelle was a terrific host. I would highly recommend staying here.
Chalet in Gravenhurst
4.89 out of 5 average rating, 62 reviews

Muskoka Mist

SarahRating, 5 stars3 months ago
Our family stayed at Antonio’s place for a week and we really enjoyed our stay. The cottage was very clean and as described. The beds were very comfortable and we all had good sleeps the entire week! The area was very safe and peaceful and the cottage was well stocked so we literally just needed to bring food and clothes and we were set. The location is very well located between Gravenhurst and Bracebridge so everything is close by and very accessible. We would definitely recommend this cottage and would love to return for another vacation in the future.
Chalet in Gravenhurst
4.76 out of 5 average rating, 42 reviews

Lakefront Retreat, Cathedral Ceilings & Fireplace

BriannaRating, 5 stars5 months ago
We stayed with a group of friends over the New Years holiday, and it was the perfect peaceful setting! Lots of communal space to hang out, play games, eat meals. The view from the back windows and deck was stunning as well!
Guest favourite
Chalet in Wiarton
5 out of 5 average rating, 18 reviews

Serene Waterfront Retreat

KarlRating, 5 stars1 week ago
the stay was beautiful perfect dock and beach area house was clean and welcome package was lovely touch
Top Guest favourite
Chalet in Gravenhurst
4.94 out of 5 average rating, 236 reviews

Log Cabin on the Lake Bed and Breakfast

CharleneRating, 5 stars1 day ago
My boyfriend and I rented Steve’s cabin for a birthday weekend and loved our stay. It was both recharging and relaxing. Being surrounded by nature all weekend felt grounding and the quiet was just what we were looking for. The bed was so comfortable and the whole cabin was so clean. Communication with Steve was great and he was so nice to chat with when we arrived. Although his home is just next door you’d never know he was even on the property unless you needed him. We did quite a bit of fishing during our stay and caught a pike on the first night! Thanks for a great stay!
Guest favourite
Chalet in Severn Bridge
5 out of 5 average rating, 23 reviews

The Cozy Camp Cottage and Jean Lodge

IanRating, 5 stars4 weeks ago
Camp Winston is by far the best Air Bnb I've ever stayed at. They had absolutely everything. Kayaks, canoes & paddle boats. Right on the water just steps away. Beautiful dock & boathouse area, as well as, a separate area to walk out from. The water is very shallow until a long way out. All sand with no seaweed or grime in the lake. We were able to hang out in the boathouse whereas I'd never step foot in the water of any other boathouse. Great for fishing & outdoor activities. Multiple fire pits. One located by the water for an amazing fire underneath the stars. Very private location with nobody around. The upstairs games room was massive & had room for anything & everything. The foosball tables & air hockey table were a nice touch. I would highly recommend Camp Winston to everyone & hope I can go back soon. The place had everything we needed & more! Perfect for big groups. If you see Camp Winston is available for your weekend, book it ASAP! You'll thank me.
Superhost
Chalet in Port Severn
4.64 out of 5 average rating, 83 reviews

Private Scenic Muskoka Lakefront Cottage (Hot Tub)

MikeRating, 5 stars3 weeks ago
Great cottage for a large group. The sauna was amazing!
Top Guest favourite
Chalet in Mulmur
5 out of 5 average rating, 36 reviews

Country Oasis - 5 private acres with hot tub

VeronicaRating, 5 stars8 months ago
During our stay at Jen’s cottage, we were truly impressed by how accommodating it was. We all have small children so this place was perfect as it had activities such fishing, volleyball, chess and board games and so much more. At one point the kids even had fun gathering the leaves in the front yard. This place is spacious, had everything you could possibly need for a nice getaway from the city and it’s still close to home. We had the most amazing time and will definitely be coming back soon. Thank you to Jen for being the most wonderful host and letting us use her home!

Quick stats about chalet rentals in Grey Highlands

  • Total rentals

    190 properties

  • Nightly prices starting at

    $83 NZD before taxes and fees

  • Total number of reviews

    13K reviews

  • Family-friendly rentals

    180 properties are a good fit for families

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with a pool

    40 properties have a pool

Destinations to explore

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  5. Grey Highlands
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