
Pet-friendly holiday rentals in Grey Highlands
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Top-rated pet-friendly home rentals in Grey Highlands
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Popular amenities for Grey Highlands pet-friendly home rentals
Pet-friendly house rentals

Sunnyside Stay-3bdrm w/ Gym!
We had a wonderful stay here in Midland. The house is very clean and spacious and the master bedroom is a great space to unwind and relax. The house did not disappoint and I would book again for our next trip to Midland. Nicole is a great host, and excellent communicator and was very helpful.

Theniceday - Family Friendly House
Great location. Amy was a wonderful host and she made sure we were well

Charming 3 bed house, your gateway to Georgian Bay
Lovely spot to stay with the family. We had such a nice weekend. Meaford is great place and close to both Owen sound and Collingwood to explore further. The house was comfortable and a great place for our family and dog to relax. It had everything we needed

Simcoe Retreat
From the moment I opened the door I was in love with Alison's place! It was bright, warm and welcoming (not to mentioned beautifully decorated). There were too many amenities to mention and so many thoughtful touches. Alison was an excellent host, allowing me to check in early and always responding in a timely manner. Alison's place has definitely raised the bar for me when it comes to Airbnb stays. I would 100% recommend Alison....you will not be disappointed!

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

Spacious N Bright 3Bd/1.5Ba Updated Suite/Parking
Host was very friendly and accommodating. The place was very clean and inviting. would definitely recommend to anyone! great Host.

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!

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.
Pet-friendly home rentals with a pool

Farmhouse GUEST SUITE- Pool, hot tub, horses
We stayed at Amanda and Mike’s Airbnb in Minesing for a 3-day cottage vacation and had an amazing time! The farmhouse was the perfect size for the two of us. The place was very clean. The kitchen was fully stocked with everything we needed, and the hot tub very nice and the instructions given for operating were easy to follow. It was very quiet, peaceful, and the perfect relaxing getaway from the city. We would definitely recommend this place to friends and family and would love to come back again!

Large 4 Br - 4.5 Bath; Sauna/Shuttle Bus/2 King bd
This was a great home with lots to do inside. We enjoyed all of the games and pool table. Shuttle service was easy to use and only a short ride away to the village. The beds were comfortable and lots of space inside for our family. Brendan was friendly and responsive!

Harper Cabin
wonderful atmosphere! Great amenities, close to beaches and lots of local attractions. The people were great, staff was excellent. Wood deliveries and all! I will be back!

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.

*Haven on Blue*- Hot Tub, Heated Pool & Sauna
Great place - cozy and so close to the hill. Didn’t have a chance to use the sauna so hopefully next time :)

Great kitchen, comfy beds, games, walk 2 village +
Jason and Tanya saved our trip after the first Airbnb we checked into was dirty and had mice! They had a last minute cancellation and allowed us to check in right away! They were super helpful in getting us moved over to their place. When we got inside it was beyond clean and comfortable. The kitchen was the best of any airbnb I've stayed in with spotless dishes and useable pots/pans and appliances. The unit is spacious and the beds & linens were extremely comfortable. A million thanks for saving our trip for us! Would highly recommend to anyone.

Blue Mountain Escape! Pool&HotTub. Walk to Village
This is a fantastic find! It's a short walk to Blue Mountain village and a short drive to Collingwood. The place is very spacious and comfy with bedrooms on different levels. The kitchen is well stocked if you want to do any cooking and the hot tub was wonderful. San was very helpful, friendly and accommodating, and would also reply pretty quickly. I'd definitely recommend this place and would absolutely stay here again!

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!
Private, pet-friendly home rentals

Cheerful bunkie on ranch
Excellent stay, check in was easy and place was sparkling clean. Very spacious and well equipped. We spent our days cross-country skiing in nearby nordic centers and enjoying the evenings at home. Would definitely stay again!

Woodski Mountain Retreat w/Pool & 3+ Private Acres
We had an amazing stay at this cozy cottage for the weekend! It was beautifully decorated, super clean, and had everything we needed. The peaceful location was perfect for relaxing, yet close to nearby attractions. Our host was thoughtful and communicative, making sure we had a great experience. We can’t wait to return!

Two units in Horseshoe Valley
Great spot, very clean wonderful communication

Blue Mountain Studio, 2 Queen Beds, Lake Huron
Great place with a wonderful host. Can’t wait to stay here again

Cozy 4 Season Family Cottage
Anthony’s place was the perfect spot for a nice weekend! We really enjoy having a relaxing fire in the backyard with plenty of wood. We would definitely consider staying here in the future!

Memories Are Made Here
Great place in such a beautiful cozy community! Communication with Ali was fast and easy and his cottage was clean and bunch of useful amenities. 10 min walk from beach, overall great experience!

Chic Pad w/ Yard Richmond Hill
She was responsive and a good communicator. We had everything we needed. It was a nice stay and convenient. The washer and dryer were not hooked up but didn’t bother us. Everything was great!

Romantic Cabin Getaway with Hot Tub
“Hostess with the mostest” is an understatement for Sandra. When she says all you need to bring is your overnight bag and groceries, she means it! Her and Dejay are lovely people, offering an incredible getaway. The attention to detail and commitment to their guests is unmatched. 10/10 would recommend and return!
Quick stats about holiday rentals that are pet-friendly in Grey Highlands
Total rentals
530 properties
Total number of reviews
30K reviews
Family-friendly rentals
450 properties are a good fit for families
Rentals with a pool
150 properties have a pool
Rentals with dedicated workspaces
310 properties have a dedicated workspace
Wi-Fi availability
500 properties include access to Wi-Fi
Destinations to explore
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- Family-friendly rentals Grey Highlands
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- Blue Mountain Village
- Horseshoe Resort
- Mount St. Louis Moonstone
- TPC Toronto at Osprey Valley
- Snow Valley Ski Resort
- Osler Bluff Ski Club
- Beaver Valley Ski Club
- Hockley Valley Resort - Golf, Spa and Ski
- Devil's Glen Country Club
- Cobble Beach Golf Resort Community
- Legacy Ridge Golf Club
- Alpine Ski Club
- National Pines Golf Club
- Inglis Falls
- The Georgian Peaks Club
- The Georgian Bay Club
- Toronto Ski Club
- The Pulpit Club
- Caledon Country Club
- Shanty Bay Golf Club
- The Club At Bond Head
- Craigleith Ski Club
- Mad River Golf Club
- Mansfield Ski Club