
House vacation rentals in Grey Highlands
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Top-rated house rentals in Grey Highlands
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Vacation rentals for every style
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Popular amenities for Grey Highlands house rentals
House rentals with a pool

Large 4 Br - 4.5 Bath; Sauna/Shuttle Bus/2 King bd
It is a wonderful house, furnished in every detail, it offers many entertainments to have fun with your family. My children had a great time. The house is in a quiet and relaxing location surrounded by nature.

Spacious 4BR Snowbridge Home with Shuttle Access
Very nice and spacious home with plenty of room for a large group to spread out. Loved the open concept kitchen and dining area and felt plenty close to Blue Mountain village and skiing.

Serene mountainside home View/Shuttle Bus/Pool
We had a wonderful stay - Brendan's place was clean, organized and in a great area (close to village). Brendan was responsive and helpful and I would recommend this place to relax and enjoy Collingwood.

Forest Loft - Forest, Sauna, Ponds & Stargazing
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 :)

10 Acre Farmhouse with Pool + 5 Bedrooms/3 Baths
This place was absolutley spotless and communication was amazing even though nothing was needed til checkout. Would love to have enjoyed pool but tough in January. Minimal amount of snow fell and they had someone come shovel and salt.

Custom Mansion on the Water | Pool | Hot Tub
This is the second time we’ve booked a stay here - from the outside it doesn’t seem nearly as big as it actually is inside. A beautiful home with a ton of space for 14-16 of us, with enough amenities that you don’t have to leave at all during your stay, but there are also multiple nearby trails and parks to explore. The dishwasher was broken during our stay, which was quite an inconvenience for a large group, but Nicholas was accommodating and fairly responsive. Due to the holiday season there was no one available to repair it but we were fairly compensated for our troubles.

Heart of Kimberley - with views and a hot tub
Thanks for a great stay!

Stonehaven - large country retreat, with pool*
We struggled to find a place for our group of 17 and Stonehaven was an amazing find! The beds were comfortable, we loved being able to have meals all together in one spot, and there was lots of space for people to do different activities inside since it was winter. Outside, we enjoyed tobogganing, snowshoeing and cross country skiing on the property. Steve was quick to communicate and provided clear instructions and maps. We were already talking about going back so we can enjoy the property in the summer! Thank you for a memorable and fun weekend!
Weekly house rentals

WoWSaga peaceful 3bdr close to Blue Mountain
Nice place about a 10 min walk to the beach down some quiet side streets. Great fire pit in the back but the pull out couch leaves something to be desired if you sit on the wrong spot. Loved the vinyl collection and the path across the street.

King Beds with Home Gym and Large Backyard Oasis
We had a great stay in Barrie! The place was clean, cozy, and exactly as described. The host was super responsive and made everything easy. Would definitely stay again!

Luxe Villa with Sauna and Hot Tub @ Lake Simcoe
We loved the place—cozy and perfect for a relaxing weekend getaway. I really appreciated the early check-in and later check-out. Thank you! I would definitely recommend this stay

Great Family Get Away - Wasaga Beach (2) wifi
Rocco was an incredible host, accommodating to every extent possible. The place was spotless, equipped with everything you could ever need, and just steps away from the beach. To top it off, there's an amazing ice cream shop just two steps away—what more could you ask for? Rocco truly made us feel right at home and ensured our stay was comfortable and enjoyable from start to finish. I can't recommend this place enough! I just hope this review doesn’t come back to bite me, as it might mean less availability in the future for us! Def looking forward to our next visit!

Stunning 5 Bedroom Family Home
House was perfect for our group of 8. Will stay again next time we’re in the area

Townhouse 5 min to Wasaga Beach
This is a beautiful home. It is very clean and perfect for anyone. We definitely recommend staying here and would come back again. The owners were extremely responsive to any of our questions.

Sandy beach getaway
We had an amazing stay at the cottage. Everything was spotless and welcoming. Kitchen had everything we needed and we enjoyed our meals on the large deck. Located in a quiet and peaceful area. Short walk to a beautiful, clear, sandy beach. We enjoyed many spectacular sunsets. Great beach for kids. We enjoyed our stay and would highly recommend.

JJ’s Collingwood bar & games house.
Jer was a very good host, the place was beautiful, bunch of games to play, had a lot of fun. The surroundings are beautiful 10 min walk to park and beach. 10 minutes drive to blue mountain. The place was really good.
Private house rentals

All season/Ski/Waterfront/Fish Modern Cottage
We had a wonderful stay in this AirBnB! The view is a dream. You are reliant on a car here, as you can't get very far on foot, but the nearest supermarket is just a 5-minute drive away.

The Old Millinery House
We had a wonderful stay at the Old Mill in Shelburne. The property is charming and full of character, offering both comfort and tranquility. Lynn is a generous and thoughtful host, making our visit truly special. Highly recommended!

Swan Cove Waterfront Retreat
Evgenia's home was overall ABSOLUTELY STUNNING! From the beautiful water front views to the gorgeous amenities, my entire group was in awe of what was right in front of us. We had such an amazing stay, made even better memories and felt right at home during our stay. It was truly a great "home away from home" experience! We were so lucky to get the chance to feed the swans during our stay, we were shocked at the amount of wildlife that appeared thereafter. During our stay we were able to bring a boat & jet ski. We docked the jet ski at the property's dock and were able to launch the boat/jet ski at the Victoria Harbour in the area. Unfortunately we were unable to bring the boat to the home's dock due to low tide this year, but hopefully when we book again we can dock both at the house :) We would 100% recommend Evgenia's place for anyone looking for a quiet luxurious getaway with the most spectacular views!

Large 4 br and 3 full bathroom/Sauna by Village
Our stay was awesome, the house is amazing, very close to the slopes and the amenities were great!

5+ bdr Cottage Collingwood Blue Mountain Singhamp
Nancy’s Airbnb was an absolutely fantastic experience! From the moment we booked, Nancy’s communication was flawless—prompt, clear, and incredibly friendly. She provided detailed instructions and helpful tips that made our stay seamless. The property itself was immaculate, cozy, and exactly as described, with thoughtful touches that made it feel like home. Nancy clearly takes pride in hosting, as every detail was carefully considered, from the well thought out social spaces to the well-stocked amenities. Her hospitality truly stood out—she was always available to answer questions and went above and beyond to ensure we had everything we needed. It’s rare to find a host so dedicated to creating a memorable experience. We couldn’t recommend Nancy’s Airbnb more highly and will absolutely stay here again!

Entire House, Private/Clean 5bdr 6 Beds/Sleeps 12
Hi Sina! Thanks for hosting me and my family. The house was beautiful and clean. We enjoyed every minute of it. The area was very serene and had a sense of home in it. It was also near many wonderful tourist sites as well convenient stores. Although, it was a bit cold, so we couldn't enjoy it to the fullest. But we very much hope to revisit in the summer.

Century Home in downtown Owen Sound - Hot Tub
Excellent place to stay. Very clean. Very accommodating.

BlueFornia Ski Snow Sweet Home Winter
beautiful and clean place. 100% privacy as it was surrounded by trees. . everything you needed was there. .would highly recommend
Quick stats about house rentals in Grey Highlands
Total rentals
270 properties
Total number of reviews
7.3K reviews
Family-friendly rentals
240 properties are a good fit for families
Pet-friendly rentals
110 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
150 properties have a dedicated workspace
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- Blue Mountain Village
- Horseshoe Resort
- Mount St. Louis Moonstone
- Snow Valley Ski Resort
- TPC Toronto at Osprey Valley
- Osler Bluff Ski Club
- Beaver Valley Ski Club
- Hockley Valley Resort - Golf, Spa and Ski
- Devil's Glen Country Club
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- Alpine Ski Club
- Cobble Beach Golf Resort Community
- Inglis Falls
- Toronto Ski Club
- Caledon Country Club
- The Georgian Peaks Club
- National Pines Golf Club
- Shanty Bay Golf Club
- The Georgian Bay Club
- Craigleith Ski Club
- The Paintbrush
- Barrie Country Club
- Mad River Golf Club
- The Club At Bond Head