Chalet holiday rentals in Grey Highlands

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Popular amenities for chalet rentals in Grey Highlands

Family-friendly chalet rentals

Superhost
Chalet in The Blue Mountains
4.8 out of 5 average rating, 195 reviews

Chalet At Blue - Private chalet with hot tub

MercedesRating, 5 stars3 months ago
This place was perfect for a blue mountain get away. We had 8 adults stay here for a ski trip and we all were comfortable and had a wonderful time. The kitchen is well stoked so we were able to make large communal meals with no issues. I'll definitely look into coming back next year.
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!!
Superhost
Chalet in The Blue Mountains
4.69 out of 5 average rating, 77 reviews

Rustic 5BR Escape | Sauna, Hot Tub, Mountain Views

RoccoRating, 5 stars1 month ago
Colin was an amazing host and our group loved staying at his place. Very responsive and helpful even when a powerful storm rolled through during our stay. The basketball court was very popular in our group despite the rim having been fairly damaged by one of the previous groups that stayed. It was awesome having a hot tub and sauna available to us. On a crispy cool day the hot tub was such a treat. The area has beautiful scenery and the AirBnb is located in a quiet and peaceful spot. Perfect for hanging out near the firepit or on one of the two patios. I would highly recommend this to anyone who is looking to just get away for a few days for a peaceful cottage experience.
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!
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!
Guest favourite
Chalet in The Blue Mountains
4.89 out of 5 average rating, 107 reviews

Rustic Spanish Chalet inthe Heart of Nature/hottub

GhazalehRating, 5 stars1 month ago
Our host was very respectful, responsive, and helpful throughout our stay. The cottage was well-equipped with everything we needed and offered great amenities. The location was also convenient and pleasant. Overall, we had a wonderful time here and would definitely recommend this place to others!

Luxury chalet rentals

Guest favourite
Chalet in The Blue Mountains
4.97 out of 5 average rating, 62 reviews

Lake/Ski chalet with HOT TUB1

KenRating, 5 stars4 months ago
Great place for our multigenerational hangout. Tons of space to sprawl out, great location for a walking to village and skiing. Hot tub was loved by all
Top guest favourite
Chalet in The Blue Mountains
4.94 out of 5 average rating, 48 reviews

The Blue Bear Classic Chalet w/ BBQ, Large Backyar

JaimesonRating, 5 stars1 month ago
We had a great stay at Tony’s! Excellent location, walkable to Blue Mountain. Lots of space. Very nice living area and big dinning table. Plenty of dishes and cooking tools. Great place for many people to stay! Would definitely come back. Tony was also so friendly and responsive to any questions we had.
Guest favourite
Chalet in The Blue Mountains
4.97 out of 5 average rating, 88 reviews

Walk To Ski Hill- HOT TUB & SAUNA

BrettRating, 5 stars3 weeks ago
This house was exactly like the pictures, great hot tub and sauna, big rooms and comfortable beds. Right at the base of the mountain close to all amenities.
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
4.76 out of 5 average rating, 135 reviews

Timberline Lodge: Luxury 4 Floor Chalet w/ Hot Tub

MalloryRating, 5 stars1 week ago
We have no complaints, stay here with a group of ladies and we were very impressed with this chalet. It was clean, very spacious, well equipped and great location. We would definitely stay here again!
Superhost
Chalet in The Blue Mountains
4.81 out of 5 average rating, 27 reviews

Lake/Ski chalet with HOT TUB/SAUNA!

LindsayRating, 5 stars1 week ago
We had a fantastic stay at Vlad and Elena's house. The layout was perfect and we had lots of space for 12 guests. Everything was very clean. It was the perfect place to unwind and relax after a busy day at Blue Mountain. The kitchen was beautiful and had everything we needed. The location was very private. I would definitely recommend and hope to be back myself sometime!
Superhost
Chalet in The Blue Mountains
4.72 out of 5 average rating, 106 reviews

Blue Birds Inn Collingwood, The Blue Mountains

SoniRating, 5 stars9 months ago
Anthony's place was nice and we enjoyed our stay. Place is very well stocked with towels, dishes, utensils and extra propane. We had a few concerns which Anthony adressed. Pool - house by the dirt road and thus traffic will cause dirt to enter pool. We advised Anthony and he promptly gave us access to the skimmer and we were able to clean the pool. Temperature is set at 80F, DO NOT increase the temperature or a fee of minimum $1500 applies if liner comes out or $5000 if liner needs replacing. This is stipulated in the contract you have to sign at check in Leak- master shower leak from damaged caulking causing water leak downstairs from the pot lights. We advised and stopped using the shower immediately. Anthony said was the first time and was going to repair the leak. Beds- bunk beds need safety railings due to safety hazard for children. Bring your own pillows if you like fluffy or firm. Anthony had offered an exclusive rate and was very kind. Would visit again.
Guest favourite
Chalet in The Blue Mountains
4.91 out of 5 average rating, 254 reviews

Relax at The Mountaintop Chalet (sleeps 16)

Grant & ChaniseRating, 5 stars1 month ago
We had a great stay. The photos don’t do it justice! This place is beautiful and clean. We loved our stay and would love to book again in the future.

Lakefront chalet rentals

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!
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.
Guest favourite
Chalet in Wiarton
5 out of 5 average rating, 19 reviews

Serene Waterfront Retreat

RichardRating, 5 stars6 days ago
Great spot - on the water and yet close to town. Quiet dead end street and large sloping yard. Recommend!
Guest favourite
Chalet in Severn Bridge
5 out of 5 average rating, 23 reviews

The Cozy Camp Cottage and Jean Lodge

IanRating, 5 stars1 month 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

    $64 SGD 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

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