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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
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
4.99 out of 5 average rating, 96 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, 40 reviews, 4 bedrooms, 4 beds, 2 bathrooms
31 Aug – 5 Sept
Top guest favourite
Home in Flesherton
Renovated 3-BR Home Near Old Baldy | BBQ & Hot Tub
4.98 out of 5 average rating, 43 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
6–11 Jul
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
Tiny home in Maxwell
New waterfront bunkie with loft
4.64 out of 5 average rating, 44 reviews, 1 bed, 1 bathroom
5–10 Jul
Guest favourite
Cottage in Kimberley
A Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi
4.85 out of 5 average rating, 376 reviews, 5 bedrooms, 7 beds, 5 bathrooms
12–17 Jul
Top guest favourite
Barn in Eugenia
Blue Barn Bed n Bale / Blue Mountain
4.98 out of 5 average rating, 207 reviews, 2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
Top guest favourite
Guest suite in Kimberley
"Wine Down" in Scenic Grey Highlands
4.97 out of 5 average rating, 268 reviews, 2 bedrooms, 5 beds, 1 bathroom
4–9 Oct
Flat in Meaford
Scenic Stable Apartment on 147-Acre Horse Farm
New place to stay, 3 bedrooms, 3 beds, Toilet with sink
5–10 Jul
Home in Markdale
TnG’s Country Airbnb
4 bedrooms, 4 beds, 2 bathrooms
18–23 Jul
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
29 Aug – 3 Sept
Top guest favourite
Chalet in The Blue Mountains
Stylish Log Chalet w/ Hot tub Minutes to Village
4.91 out of 5 average rating, 105 reviews, 3 bedrooms, 6 beds, 1.5 bathrooms
5–10 Jul
Home in Collingwood
*NEW*Collingwood Home-Private HotTub FirePit & BBQ
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Top guest favourite
Dome in Priceville
Dream Capsule | 3-Season Glamping Escape in Nature
5.0 out of 5 average rating, 30 reviews, 1 bedroom, 1 bed, Toilet with sink
9–14 Jul
Top guest favourite
Yurt in Meaford
Quiet Retreat for Two
4.99 out of 5 average rating, 194 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Guest suite in Kimberley
The Post Office Motel & Spa in the ❤️ of Kimberley
4.94 out of 5 average rating, 834 reviews, 1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept
Home in Markdale
Luxury Beaver Valley Chalet | Hot Tub, Sauna, View
4 bedrooms, 7 beds, 4.5 bathrooms
6–11 Jul
Top guest favourite
Farm stay in Kimberley
Valley View Farm Retreat ~ Family, Pets, Hiking
4.95 out of 5 average rating, 121 reviews, 4 bedrooms, 6 beds, 2 bathrooms
8–13 Sept