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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
4.99 out of 5 average rating, 99 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Sept
Guest favourite
Home in Grey Highlands
Rosewood Parlour AFrame - by The Post Office Motel
4.98 out of 5 average rating, 43 reviews, 4 bedrooms, 4 beds, 2 bathrooms
29 Aug – 3 Sept
Superhost
Tiny home in Maxwell
New waterfront bunkie with loft
4.66 out of 5 average rating, 47 reviews, 1 bed, 1 bathroom
9–14 Aug
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
22–27 Aug
Top guest favourite
Cottage in Southgate
Luxurious Creek Retreat With Hot Tub
4.99 out of 5 average rating, 181 reviews, 2 bedrooms, 2 beds, 1 bathroom
21–26 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
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
Cabin in Kimberley
Deer Park, Cozy Cabin with Hot Tub, Amazing View
4.81 out of 5 average rating, 255 reviews, 3 bedrooms, 3 beds, 1 bathroom
21–26 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
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
18–23 Jul
Top guest favourite
Dome in Markdale
Forest Dome
4.95 out of 5 average rating, 265 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
16–21 Aug
Top guest favourite
Chalet in The Blue Mountains
Stylish Log Chalet w/ Hot tub Minutes to Village
4.92 out of 5 average rating, 107 reviews, 3 bedrooms, 6 beds, 1.5 bathrooms
20–25 Jul
Guest favourite
Home in Collingwood
The Light House
4.92 out of 5 average rating, 13 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
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
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
Dome in Priceville
Dream Capsule | Stargazing Glamping Escape
5.0 out of 5 average rating, 31 reviews, 1 bedroom, 1 bed, WC
19–24 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
Home in West Grey
Woodland River Retreat With Hot Tub
4.95 out of 5 average rating, 21 reviews, 2 bedrooms, 2 beds, 1 bathroom
10–15 Sept