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Search results; Over 1,000 homes in Grey Highlands

Top guest favourite
Loft in Grey Highlands
The Carriage House @ Trillium Shores, Lake Eugenia
3 bedrooms, 5 beds, 1.5 private bathrooms
9–14 Aug
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4.9 out of 5 average rating, 125 reviews
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
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
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
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
Tiny home in Flesherton
The Hideaway - Tiny House
4.81 out of 5 average rating, 197 reviews, 1 bedroom, 2 beds, 1 bathroom
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
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
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
Home in Markdale
TnG’s Country Airbnb
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Superhost
Tiny home in Maxwell
New waterfront bunkie with loft
4.64 out of 5 average rating, 45 reviews, 1 bed, 1 bathroom
9–14 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
Top guest favourite
Barn in Eugenia
Blue Barn Bed n Bale / Blue Mountain
4.98 out of 5 average rating, 209 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Cottage in Flesherton
All-Season Cottage on the Lake
4.95 out of 5 average rating, 152 reviews, 3 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Cottage in Kimberley
Cozy Summer Getaway | Hot Tub Sauna BBQ & Firepit
4.89 out of 5 average rating, 127 reviews, 5 bedrooms, 10 beds, 2.5 bathrooms
19–24 Jul
Home in Flesherton
Luxury Lakefront Log Retreat On 100 Acres
4.8 out of 5 average rating, 10 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
9–14 Aug
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
Chalet in Meaford
Sundance of Blantyre Lodge +Hot Tub +Sauna +Pond
4.98 out of 5 average rating, 130 reviews, 7 bedrooms, 9 beds, 3.5 bathrooms
30 Aug – 4 Sept
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