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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
19–24 Jul
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4.95 out of 5 average rating, 158 reviews
Top guest favourite
Cabin in Kimberley
Private Luxury Creekside Cabin with Sauna
4.99 out of 5 average rating, 99 reviews, 1 bedroom, 2 beds, 1 bathroom
7–12 Aug
Guest favourite
Home in Grey Highlands
Rosewood Parlour AFrame - by The Post Office Motel
4.98 out of 5 average rating, 42 reviews, 4 bedrooms, 4 beds, 2 bathrooms
29 Aug – 3 Sept
Guest favourite
Cabin in Grey County
Beaver Valley Hike, Bike & Ski Cottage
4.89 out of 5 average rating, 35 reviews, 3 bedrooms, 3 beds, 1 bathroom
5–10 Aug
Top guest favourite
Tiny home in Kimberley
Hand-Crafted Cabin in Stunning Beaver Valley
4.98 out of 5 average rating, 174 reviews, 1 bed, 1 bathroom
18–23 Jul
Home in Mulmur
Escarpment House | Modern Country Retreat
New place to stay, 3 bedrooms, 4 beds, 3.5 bathrooms
14–19 Jul
Guest favourite
Guest suite in Kimberley
The Post Office Motel & Spa in the ❤️ of Kimberley
4.94 out of 5 average rating, 838 reviews, 1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept
Superhost
Home in Meaford
Greystone Lavender Farm-Hot Tub|Pool Table|KoiPond
New place to stay, 4 bedrooms, 9 beds, 3.5 bathrooms
26–31 Jul
Top guest favourite
Home in Flesherton
Renovated 3-BR Home Near Old Baldy | BBQ & Hot Tub
4.98 out of 5 average rating, 44 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
25–30 Jul
Top guest favourite
Guest suite in Kimberley
"Wine Down" in Scenic Grey Highlands
4.96 out of 5 average rating, 272 reviews, 2 bedrooms, 5 beds, 1 bathroom
11–16 Oct
Guest favourite
Tiny home in Meaford
Tiny Home Nestled between Thornbury & Meaford
4.86 out of 5 average rating, 436 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Superhost
Place to stay in Maxwell
Waterfront Cabin on private trout Lake
4.76 out of 5 average rating, 172 reviews, 3 beds, WC
30 Aug – 4 Sept
Guest favourite
Cottage in Kimberley
A Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi
4.85 out of 5 average rating, 378 reviews, 5 bedrooms, 7 beds, 5 bathrooms
26–31 Jul
Guest favourite
Cottage in Flesherton
Modern all-season cottage overlooking Lake Eugenia
4.95 out of 5 average rating, 100 reviews, 3 bedrooms, 4 beds, 1 bathroom
9–14 Aug
Top guest favourite
Cottage in Grey Highlands
Hilltop garden cottage
4.93 out of 5 average rating, 187 reviews, 3 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Home in Kimberley
Beaver Valley Vista: Secluded w Hot Tub, Fire Pit
5.0 out of 5 average rating, 50 reviews, 4 bedrooms, 7 beds, 2 bathrooms
9–14 Aug
Guest favourite
Flat in Markdale
Dee’s Hideaway
4.95 out of 5 average rating, 37 reviews, 1 bedroom, 2 beds, 1 bathroom
14–19 Jul
Flat in Flesherton
Green Highlands
4.67 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Jul
Top guest favourite
Home in Collingwood
*NEW*Collingwood Home-Private HotTub FirePit & BBQ
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–14 Aug