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

Cute and Cozy House
After being displaced from our home after damage from severe weather we were so fortunate to find this location. The house accommodated our family of 4 with pets for nearly a month without any issues. The kitchen is well equipped, bathrooms are well finished, bedrooms were comfortable and the location was very clean. The backyard is a beautiful and relatively private space hidden within a 15 minute walk to the downtown restaurants or the beach area. Anzhelika is an excellent host who was very responsive when needed, provided clear instructions and ample privacy. We would happily recommend this location to friends and family attending the area for events.

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts
We had a wonderful stay in this beautiful house. We booked it for a small get-together with our friends. The house is spacious and beautifully decorated. Jerry made sure everything was set up to make our stay comfortable. Although the pool wasn’t open during our visit, it’s definitely something we’re looking forward to next time. We are glad we chose this place. Thanks again for hosting us!

4BR Family Home w/ Pool Access + Village Shuttle
We really enjoyed our stay! The home was large and very clean, and in a great location for going to the spa and into the village.

Heated Pool-tub Open 365 Days
Miles is a fantastic host! Not only was he proactive in communicating details regarding entry and amenities, he went above and beyond with little fresh baked goods, Smart Home instructions guide, and providing literally everything you'd need to feel at home (bathrobes, teas, serving dishes+several cups, even milk and cream in the fridge!) The Hot tub was great, the place was spotlessly clean, and the balcony views were a pleasure to enjoy. This is a great house with lovely sky lights in the kitchen and beautiful location right by the boardwalk! 11/10 ✨

10 Acre Farmhouse with Pool + 5 Bedrooms/3 Baths
This place is the perfect getaway for anyone looking to relax and enjoy quality time with family and friends. Surrounded by beautiful nature and fresh air, it offers a peaceful, private setting that’s ideal for both adventure and quiet moments. I highly recommend it to anyone seeking a refreshing escape.

Toronto Pool Retreat
Meysam’s place was a great fit for our large group. The location was convenient for getting around, and the house offered everything we needed for a comfortable stay. There was plenty of space to cook and hang out together, and the hot tub was a nice feature. Overall, a solid spot for a group getaway.

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!

King West Victorian Studio Gem
What an absolute gem of a house! I felt right at home and so relaxed with the cherry tree blooming in the back yard. Kathleen added thoughtful details and helpful instructions. The house was within walking distance of amazing restaurants, cafes and shops.
Weekly house rentals

King Beds with Home Gym and Large Backyard Oasis
Very nice place in a quiet neighbourhood.. steps away from my nature trail

Mono Mills Home next to the County Great Getaway
We were displaced by a fire and lucky to find this spot to call home until we found our forever home. Trudy and Ray were both friendly and supportive. Big backyard was nice for our little guy to play in, safe and quiet spot as well. Thank you for having us!

2min walk to the beach & 20 min drive to Blue Mnt
Lovely place, friendly but unobtrusive host! Great for family!

4 Bedroom Fully Private Townhouse in Barrie
Muhammad's place was clean,quiet and private. Muhammed was easy to get ahold of and very accommodating I recommend this stay to anyone. Thank you for you hospitality. Ryan

Entire House, Private/Clean 5bdr 6 Beds/Sleeps 12
Had a great time staying here with 6 people including myself. Great location. It was close to everything we wanted. 4 mins to Tims. 13 mins to downtown. and 25 mins to Horseshoe Valley Resort. Beds were decent. Couches were very comfortable, and my back isn't the best. So that was a nice feature. Back deck was very nice. We had no issues with the neighbors, even though I was worried based on one of the other reviews. We only used 3 cars, and parked in a row on our side of the driveway. We enjoyed our stay a lot. Would definitely recommend.

3 bdr home + bsmt in Swansea/High Park
we lived Johan's hosted house over two and half months. it's a pleasant staying. It's cozy and beautiful neighborhood , short distance to subway and almost everything in the walkable distance. Johan is such a responsible and considerate host, We do enjoy our staying.

The Nest at Victoria Street
Would definitely recommend staying at the Nest. The location is very close to the centre of town, and walkable to the beach and fairy lake. The Nest itself is very cozy and has everything you need, and Sheila is a very responsive and welcoming host!

Luxury 5 beds, 6 Baths custom home
An amazing home meeting the needs of our multi-generational family spending a week together in the GTA to cheer on our daughter participating in a National sporting event. Listing is reflective of the gorgeous, clean home. We would definitely look to return should another opportunity present!
Private house rentals

Cozy Cottage with Private Beach Access
Thanks for having us! Lovely home, great neighborhood, huge backyard.

Private log cottage on 2 acres
Natalia's listing was spot on, easy to get to and very well kept. Guests are going to book her place hopefully next summer for their family. Great for all ages. I would recommend Natalia's place as a destination for AIRbnb. Ken

Luxe Villa with Sauna and Hot Tub @ Lake Simcoe
Great stay. Private and peaceful area, but within walking distance to the vibrant Friday Harbor. We have had lovely time. Thanks Alex!

Luxurious Spacious Dream Home with Parking!
Romalis place was Beautiful comfortable, so spacious and clean!!

Riverside Retreat /w Pool,Hot Tub & Sauna in Elora
The Crystal Retreat was really a fun vacation spot, and especially interesting as architecture buffs. The house is a custom home built in 1978 with the plans framed and on display. It is a unique and beautiful house with so much to enjoy on the property. We managed to check off everything over the course of four days, but needed at least that much time to get to all the pretty and relaxing spots throughout. From getting cozy with a movie with a tv that spins to face all the various lounging nooks, to diving in the pool, canoeing to the Elora Quarry, vegging out by the fire pit, we did it all and are thankful to Djurdjica for sharing her special home.

Cheerful 3 bedroom home with outdoor pool & hottub
An absolutely stunning property with great amenities - the hot tub soak was super appreciated. Instructions to get to the property and check-in are super clear, and everything is clearly labelled in the house. Paige supplies everything you need at the house to cook, clean up, and keep everything running. She is super responsive and very helpful! Thank you for a lovely stay and we are already hoping to come back!

Skyhouse - Private Beach Access
The place we stayed at was great, and whenever there was a problem Irena found a quick solution that worked with both her and I. Great people great stay. 10/10

Entire Vacation Home in Barrie
John and Monica’s place was perfect for my family to stay after a wedding in the area. Felt right at home. It was clean and just as described. John and Monica were very responsive, allowing us to check in early. Thank you for a wonderful stay, we 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
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