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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
Top guest favourite
Cabin in Kimberley
Private Luxury Creekside Cabin with Sauna
1 bedroom, 2 beds
12–17 Sept
4.99 out of 5 average rating, 99 reviews
Guest favourite
Home in Grey Highlands
Rosewood Parlour AFrame - by The Post Office Motel
4 bedrooms, 4 beds
29 Aug – 3 Sept
4.98 out of 5 average rating, 43 reviews
Top guest favourite
Cottage in Southgate
Luxurious Creek Retreat With Hot Tub
2 bedrooms, 2 beds
21–26 Oct
4.99 out of 5 average rating, 181 reviews
Superhost
Tiny home in Maxwell
New waterfront bunkie with loft
1 bed
9–14 Aug
4.66 out of 5 average rating, 47 reviews
Guest favourite
Cabin in Grey County
Beaver Valley Hike, Bike & Ski Cottage
3 bedrooms, 3 beds
22–27 Aug
4.89 out of 5 average rating, 35 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, 436 reviews
Guest favourite
Guest suite in Kimberley
The Post Office Motel & Spa in the ❤️ of Kimberley
1 bedroom, 3 beds
30 Aug – 4 Sept
4.94 out of 5 average rating, 838 reviews
Superhost
Cabin in Kimberley
Deer Park, Cozy Cabin with Hot Tub, Amazing View
3 bedrooms, 3 beds
21–26 Jul
4.81 out of 5 average rating, 255 reviews
Top guest favourite
Dome in Markdale
Forest Dome
1 bedroom, 1 queen bed
16–21 Aug
4.95 out of 5 average rating, 265 reviews
Guest favourite
Home in Collingwood
The Light House
2 bedrooms, 2 beds
19–24 Jul
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Chalet in The Blue Mountains
Stylish Log Chalet w/ Hot tub Minutes to Village
3 bedrooms, 6 beds
20–25 Jul
4.92 out of 5 average rating, 107 reviews
Home in Flesherton
Luxury Lakefront Log Retreat On 100 Acres
3 bedrooms, 3 beds
9–14 Aug
4.8 out of 5 average rating, 10 reviews
Top guest favourite
Barn in Eugenia
Blue Barn Bed n Bale / Blue Mountain
2 bedrooms, 2 queen beds
18–23 Jul
4.98 out of 5 average rating, 209 reviews
Top guest favourite
Cottage in Kimberley
Cozy Summer Getaway | Hot Tub Sauna BBQ & Firepit
5 bedrooms, 10 beds
19–24 Jul
4.89 out of 5 average rating, 127 reviews
Top guest favourite
Dome in Priceville
Dream Capsule | Stargazing Glamping Escape
1 bedroom, 1 queen bed
19–24 Jul
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in West Grey
Woodland River Retreat With Hot Tub
2 bedrooms, 2 beds
10–15 Sept
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Guest suite in Nottawa
The Nottawa Post Office Inn
1 bedroom, 1 bed
16–21 Aug
4.97 out of 5 average rating, 168 reviews
Top guest favourite
Home in Flesherton
Renovated 3-BR Home Near Old Baldy | BBQ & Hot Tub
3 bedrooms, 3 queen beds
25–30 Jul
4.98 out of 5 average rating, 44 reviews