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

Close to Beach & Trails with Large Fenced in Yard
This is our second year staying over Christmas and using this place to host our families. It has everything we need to put on a dinner and enjoy the holiday. The place is clean and comfortable and has plenty of room to meet our needs. Jesse is very responsive and is eager to help if they can. We can't wait for our next stay.

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.

Tiny House in Penetanguishene
We had a great staycation! It was pet friendly and we would definitely come again. Carla was extremely responsive with our questions. We loved the endless movie options and various game boards.

Charming 3 bed house, your gateway to Georgian Bay
The place was very clean and the location it’s amazing, you are close to a lot of trails and to Blue Mountain Village. Jennifer and Keith were very responsive and friendly. It was a great experience!

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.

Driftwood on 6th Heritage Downtown Collingwood
We thoroughly enjoyed our time here. Seema's home is even more lovely than in pictures. The kitchen was fully stocked with everything you could possibly need. The beds were very comfortable and linens were high quality. This is always a make or break deal for me. The living room with big screen TV and comfy furniture was the perfect spot for us girls to relax and catch up. One thing to note is that both bathrooms are on the main floor. If you are one to get up through the night, she has installed 3 motion lights that come on as you go down the stairs. We really appreciated this safety measure. The backyard looked gorgeous. Unfortunately, we didn't have the best weather so we could not enjoy it. We'll look forward to using it the next time we book Seema's lovely home as we will most definitely be back!

Cheerful 3 bedroom home with outdoor pool & hottub
We loved our time at Paige's beautiful home. Such a comfortable, cozy, unique home. The stone fireplace with the wrapping stairs is so pretty. You feel you are staying somewhere special. With being out of our home for a renovation Paige provided many staples to make day to day comfortable. We definitely will recommend staying here to our friends and family.
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
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.

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
One of the best staycation. My siblings and I are really feel grateful especially the host are very cooperative. Everything in the house are good and the place is perfect! Will recommend it 💯%. Thank you very much!

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

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
The stay was very safe and cozy. The well-cleaned and maintained building created a great atmosphere. It is one of the best B&Bs I have ever stayed in. Anthony's responses were very quick and straightforward, making everything go smoothly. I asked for an hour early check-in, and it was approved. I will definitely come back again later.

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!

1BR Boutique Suite #5 - The Lake at Blue Mountains
clean and cozy. free parking. need to bring your own cooking oil tho!

ReLive Hilltop Chalet w/brand-new hottub, sunrises
We had a great stay in this cabin on a GORGEOUS wooded property. Awesome to watch the snow fall against the old pines. I took my dog on the snowshoe trails. Very cozy and it was great to get out of the city.

OakRidge Retreat-HOT TUB 100s of acres WIFI
We met Patricia upon check-in and she had prepared the place for us in the most welcoming way. The house has such a warm cabin feeling, is super spacious and the surroundings are beautiful. The place has everything families need in terms of spaces, linens, activities, etc… We were lucky enough to enjoy the presence of a deer coming in the garden on our first night and so many other animals. Highly recommend for a quiet stay in nature in a big cottage!
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
Wifi availability
500 properties include access to wifi
Destinations to explore
- Grand River Holiday rentals
- Brampton Holiday rentals
- London Holiday rentals
- Muskoka Lakes Holiday rentals
- Vaughan Holiday rentals
- Markham Holiday rentals
- Georgian Bay Holiday rentals
- Waterloo Holiday rentals
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- Greater Toronto and Hamilton Area Holiday rentals
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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
- National Pines Golf Club
- Alpine Ski Club
- The Georgian Peaks Club
- Inglis Falls
- Toronto Ski Club
- The Georgian Bay Club
- The Pulpit Club
- The Club At Bond Head
- Caledon Country Club
- Shanty Bay Golf Club
- Mad River Golf Club
- Craigleith Ski Club
- Horseshoe Adventure Park