
Holiday houses in Grey Highlands
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Top-rated holiday rentals in Grey Highlands
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Grey Highlands
Top Guest favourite

Tent in Fergus
4.94 out of 5 average rating, 16 reviewsThe Grand Bell Glamp
ShannonRating, 5 stars5 days ago
The tent was perfect and on a beautiful site along the river. It warmed up quickly with the woodstove. The shower house was amazing. We had everything we needed for a fun glamping getaway. I would love to return.
Top Guest favourite

Chalet in Meaford
4.98 out of 5 average rating, 87 reviewsSundance of Blantyre Lodge w Hot Tub, Sauna & Pond
SabinaRating, 5 stars2 weeks ago
We thoroughly enjoyed our stay. The place was beautiful and exactly as described. Michelle was a terrific host. I would highly recommend staying here.
Guest favourite

Farm stay in Kimberley
4.96 out of 5 average rating, 23 reviewsDay Break Farm
NaomiRating, 5 stars3 weeks ago
Day Break Farm is a stunning home. It is airy and perfectly integrated into nature. It is beautifully and comfortably decorated. The views are stunning and you truly get an extraordinary experience of Beaver Valley. The house is set up more like a property rental than a "BNB" than some other Air BNBs I have rented, so just make sure you bring things like coffee, tea and some other staples you may wish to use. We were holding a "retreat" at the property, with 4 people staying on site but 12 people gathering for lunches and meetings. I would say one thing that could be improved is more access to enjoy the outdoors. More seating (there are only 2 Muskoka chairs around the fire pit), cushions (the patio furniture available was bare), and a table would be amazing (currently there is no outdoor dining available). But of course, I imagine the property is set up for how the family use it! Overall a lovely place to stay.
Guest favourite

Home in South Bruce Peninsula
4.95 out of 5 average rating, 64 reviewsPine Villa-Mediterranean Cottage with Hot Tub
KatherineRating, 5 stars2 weeks ago
Beautiful space and super responsive & accommodating hosts! The place looks exactly like the photos and was a really nice space to spend the week. The only thing I wish we knew ahead of time was that the neighbours are pretty close on all 3 sides so it does impact the privacy of the backyard at times!

Cottage in Flesherton
4.89 out of 5 average rating, 9 reviewsNordic Nook: Family Retreat with Salt Pool
TerryRating, 5 stars10 months ago
Nick’s place was wonderful. Everything was as expected and Kylie (co-host) was quick to respond to messages. The cottage was clean, well organized and has a great layout. We felt right at home. The beds and linens are of good quality. The yard is great and the pool and hot tub were definite highlights. I 100% recommend Nick’s Nordic Nook.
Guest favourite

Cabin in Tiny
5 out of 5 average rating, 12 reviewsThe Beach House, Georgian Bay, Beach View w/ Sauna
SamRating, 5 stars5 days ago
My family and I had a great time at Adam’s cottage! Incredible view of the lake, the lake water was crystal-clear. Beach house was well maintained and very clean, the interior decor was stunning! Beach house/garage had all the amenities you will need! The 2 paddle boards and 2 bikes were a great edition! we enjoyed walks/bike rides through the trails in the neighbourhood. We will definitely come back, HIGHLY recommend! Adam was very helpful, insightful, and gave fast replies! Great host!
Guest favourite

Shipping container in Berkeley
4.94 out of 5 average rating, 83 reviewsShipping container getaway in small country town
NafisaRating, 5 stars1 month ago
Tristan was very responsive and kind. This place was perfect for a long weekend getaway!
Top Guest favourite

Cabin in Markdale
5 out of 5 average rating, 16 reviewsPond View
LynnRating, 5 stars1 week ago
Andrea was an amazing host, meeting us at the road and showing us around. The grounds are beautiful, well kept with plenty of varied seating to enjoy the sun and shade. Inside, the cabin was clean and well stocked. It was newly renovated it seemed and the appliance were new and clean. There is a remote control heating and cooling system so we didn’t have to use the wood stove. There was plenty of firewood to have a nice fire outside. The TV had Netflix, Amazon Prime etc without having to sign into your own account. And the Alexa sound bar cued to music on demand. The wifi was excellent, I had to do a bit of work while there. The shower had a large overhead rain shower and a hand held and the bathroom was very clean. The beds were very comfortable, the pillows and linen smelled fresh. We brought our dog, who has knee & hip issues and the terrain was perfect for her. She easily got in and out of the water. Lots of bunnies to keep her busy! Can’t wait to come back! Thanks Andrea
Quick stats about holiday rentals in Grey Highlands
Total rentals
1.3K properties
Total number of reviews
83K reviews
Family-friendly rentals
1K properties are a good fit for families
Pet-friendly rentals
530 properties allow pets
Rentals with a pool
490 properties have a pool
Rentals with dedicated workspaces
740 properties have a dedicated workspace
Destinations to explore
- Grand River Holiday rentals
- Brampton Holiday rentals
- London Holiday rentals
- Muskoka Lakes Holiday rentals
- Vaughan Holiday rentals
- Georgian Bay Holiday rentals
- Markham Holiday rentals
- Tobermory Holiday rentals
- Kitchener Holiday rentals
- Mississauga Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Family-friendly rentals Grey Highlands
- Rentals with a patio Grey Highlands
- Rentals with a kayak Grey Highlands
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- Fitness-friendly rentals Grey Highlands
- Ski-in/ski-out rentals Grey Highlands
- Rentals with a fireplace Grey Highlands
- Rentals with a hot tub Grey Highlands
- Rentals with breakfast Grey Highlands
- Condo rentals Grey Highlands
- Rentals with a fire pit Grey Highlands
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- Rentals with pools Grey Highlands
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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