Search results; Over 1,000 homes in Grey Highlands

Guest favourite
Cottage in Grey Highlands
Private 5 Acre Chalet with Bunkie & Sauna
2 bedrooms, 5 beds, 2 private bathrooms
12–17 Jul
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4.95 out of 5 average rating, 157 reviews
Top guest favourite
Cabin in Kimberley
Private Luxury Creekside Cabin with Sauna
1 bedroom, 2 beds
4–9 Jul
4.99 out of 5 average rating, 96 reviews
Guest favourite
Home in Grey Highlands
Rosewood Parlour AFrame - by The Post Office Motel
4 bedrooms, 4 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Tiny home in Arthur
Luxury tiny home on peaceful country estate
1 bedroom, 1 queen bed
25–30 Oct
4.97 out of 5 average rating, 396 reviews
Top guest favourite
Guest suite in Kimberley
"Wine Down" in Scenic Grey Highlands
2 bedrooms, 5 beds
29 Aug – 3 Sept
4.97 out of 5 average rating, 268 reviews
Guest favourite
Tiny home in Meaford
Tiny Home Nestled between Thornbury & Meaford
1 bedroom, 1 queen bed
23–28 Aug
4.86 out of 5 average rating, 435 reviews
Top guest favourite
Guest suite in Kimberley
The Post Office Motel & Spa in the ❤️ of Kimberley
1 bedroom, 2 beds
30 Aug – 4 Sept
4.94 out of 5 average rating, 832 reviews
Top guest favourite
Dome in Priceville
Dream Capsule | 3-Season Glamping Escape in Nature
1 bedroom, 1 bed
1–6 Jul
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Cabin in Singhampton
Cabin in the Woods
3 bedrooms, 5 beds
11–16 Jul
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Tiny home in Kimberley
Boho Beaver Cabin 1 with saltwater hot tub & sauna
1 bedroom, 1 queen bed
4–9 Jul
4.99 out of 5 average rating, 147 reviews
Guest favourite
Tiny home in Maxwell
Cute waterfront bunkie
2 single beds
1–6 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Chalet in The Blue Mountains
Stylish Log Chalet w/ Hot tub Minutes to Village
3 bedrooms, 6 beds
5–10 Jul
4.91 out of 5 average rating, 105 reviews
Home in Collingwood
*NEW*Collingwood Home-Private HotTub FirePit & BBQ
2 bedrooms, 3 queen beds
5–10 Jul
New place to stay
Top guest favourite
Yurt in Meaford
Quiet Retreat for Two
1 bedroom, 1 bed
18–23 Jul
4.99 out of 5 average rating, 191 reviews
Flat in Meaford
Scenic Stable Apartment on 147-Acre Horse Farm
3 bedrooms, 3 queen beds
5–10 Jul
New place to stay
Home in Markdale
Luxury Beaver Valley Chalet | Hot Tub, Sauna, View
4 bedrooms, 7 beds
6–12 Jul
Top guest favourite
Home in Kimberley
Paradise in the Valley
3 bedrooms, 3 beds
14–19 Sept
4.98 out of 5 average rating, 52 reviews
Top guest favourite
Cabin in Grey Highlands
The Cabin in the Woods
4 bedrooms, 4 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Cottage in Grey Highlands
Hilltop garden cottage
3 bedrooms, 6 beds
8–13 Sept
4.92 out of 5 average rating, 186 reviews