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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, 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, 41 reviews, 4 bedrooms, 4 beds, 2 bathrooms
31 Aug – 5 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
28 Jul – 2 Aug
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
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
12–17 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
Superhost
Tiny home in Maxwell
New waterfront bunkie with loft
4.64 out of 5 average rating, 44 reviews, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Cottage in Flesherton
All-Season Cottage on the Lake
4.95 out of 5 average rating, 151 reviews, 3 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
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
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
Home in Markdale
Luxury Beaver Valley Chalet | Hot Tub, Sauna, View
4.67 out of 5 average rating, 3 reviews, 4 bedrooms, 7 beds, 4.5 bathrooms
9–14 Aug
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
Top guest favourite
Loft in Grey Highlands
The Carriage House @ Trillium Shores, Lake Eugenia
4.9 out of 5 average rating, 125 reviews, 3 bedrooms, 5 beds, 1.5 bathrooms
9–14 Aug
Home in Singhampton
Blue Mountain Riverside Lodge | Hottub & Sauna
4.86 out of 5 average rating, 56 reviews, 1 bedroom, 2 beds, 1 bathroom
17–22 Aug
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
Guest favourite
Guest suite in Kimberley
The Post Office Motel & Spa in the ❤️ of Kimberley
4.94 out of 5 average rating, 835 reviews, 1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept
Home in Markdale
TnG’s Country Airbnb
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 4 beds, 2 bathrooms
18–23 Jul