
Chalet holiday rentals in Grey Highlands
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Top-rated chalet rentals in Grey Highlands
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Popular amenities for chalet rentals in Grey Highlands
Family-friendly chalet rentals

Chalet At Blue - Private chalet with hot tub
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.

Stylish Log Chalet w/ Hot tub Minutes to Village
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.

Authentic Tyrolean Chalet at base of BVSC
The place was really nice and we enjoyed with our family! We would love to visit again!!

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

Octagon Chalet fire pit, close to theVillage
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!

Walk to the village at Blue - Regal
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!

Beaver Valley family chalet with a view
Great value, only 10 minutes from Beaver Valley Ski Club, quiet and safe neighbourhood, great space and rooms!

Rustic Spanish Chalet inthe Heart of Nature/hottub
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

Lake/Ski chalet with HOT TUB1
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

The Blue Bear Classic Chalet w/ BBQ, Large Backyar
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.

Walk To Ski Hill- HOT TUB & SAUNA
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.

Shale Beach House - 5mins to Blue Mtn Village!
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.

Timberline Lodge: Luxury 4 Floor Chalet w/ Hot Tub
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!

Lake/Ski chalet with HOT TUB/SAUNA!
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!

Blue Birds Inn Collingwood, The Blue Mountains
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.

Relax at The Mountaintop Chalet (sleeps 16)
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

Lakefront Retreat, Cathedral Ceilings & Fireplace
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!

Sundance of Blantyre Lodge w Hot Tub, Sauna & Pond
We thoroughly enjoyed our stay. The place was beautiful and exactly as described. Michelle was a terrific host. I would highly recommend staying here.

Serene Waterfront Retreat
Great spot - on the water and yet close to town. Quiet dead end street and large sloping yard. Recommend!

The Cozy Camp Cottage and Jean Lodge
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.

Private Scenic Muskoka Lakefront Cottage (Hot Tub)
Great cottage for a large group. The sauna was amazing!

Country Oasis - 5 private acres with hot tub
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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- Blue Mountain Village
- TPC Toronto at Osprey Valley
- Osler Bluff Ski Club
- Horseshoe Resort
- Devil's Glen Country Club
- Beaver Valley Ski Club
- Mount St. Louis Moonstone
- Snow Valley Ski Resort
- Hockley Valley Resort - Golf, Spa and Ski
- Cobble Beach Golf Resort Community
- The Club At Bond Head
- The Georgian Peaks Club
- Caledon Country Club
- Alpine Ski Club
- National Pines Golf Club
- Barrie Country Club
- Inglis Falls
- The Georgian Bay Club
- Legacy Ridge Golf Club
- Craigleith Ski Club
- The Pulpit Club
- Mansfield Ski Club
- Mad River Golf Club
- Shanty Bay Golf Club