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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
9–14 Sept
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4.95 out of 5 average rating, 158 reviews
Top guest favourite
Home in Flesherton
Renovated 3-BR Home Near Old Baldy | BBQ & Hot Tub
4.98 out of 5 average rating, 46 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
24–29 Aug
Top guest favourite
Cottage in Kimberley
Vintage School House ~ Family, Pets, Hiking
4.91 out of 5 average rating, 371 reviews, 5 bedrooms, 8 beds, 2 bathrooms
14–20 Sept
Top guest favourite
Cottage in Flesherton
Lake Eugenia all season cottage
5.0 out of 5 average rating, 24 reviews, 3 bedrooms, 6 beds, 2 bathrooms
12–17 Aug
Guest favourite
Cottage in Flesherton
Lake Eugenia-Private, Quiet Retreat
4.82 out of 5 average rating, 95 reviews, 3 bedrooms, 5 beds, 1.5 bathrooms
7–12 Sept
Home in Flesherton
Peaceful Family Retreat by Eugenia Falls
New place to stay, 4 bedrooms, 6 beds, 2 bathrooms
12–17 Aug
Guest favourite
Tiny home in Meaford
Tiny Home Nestled between Thornbury & Meaford
4.86 out of 5 average rating, 439 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Guest favourite
Home in Markdale
TnG’s Country Airbnb
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
Flat in Flesherton
Green Highlands
4.67 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Superhost
Place to stay in Maxwell
Waterfront Cabin on private trout Lake
4.76 out of 5 average rating, 172 reviews, 3 beds, WC
30 Aug – 4 Sept
Guest favourite
Cottage in Flesherton
Private Waterfront, Dock — Lake Eugenia Escape
4.95 out of 5 average rating, 44 reviews, 3 bedrooms, 6 beds, 1 bathroom
24–29 Aug
Top guest favourite
Apartment in Collingwood
Modern & Chic Sanctuary Suite in Collingwood
4.94 out of 5 average rating, 838 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Cabin in Flesherton
MapleHaven Cabin @ Lake Eugenia
4.96 out of 5 average rating, 123 reviews, 3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
Top guest favourite
Guest suite in Nottawa
The Nottawa Post Office Inn
4.97 out of 5 average rating, 170 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
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
9–14 Aug
Home in Southgate
Modern Home | Office | Free Parking | Sleeps 4
New place to stay, 2 bedrooms, 1 bed, 2.5 bathrooms
2–7 Aug
Home in Grey Highlands
*Lake House Escape* 4 BR Family Cottage on Water
New place to stay, 4 bedrooms, 5 beds, 2 bathrooms
4–9 Aug
Top guest favourite
Barn in Eugenia
Blue Barn Bed n Bale / Blue Mountain
4.98 out of 5 average rating, 210 reviews, 2 bedrooms, 2 beds, 1 bathroom
10–15 Aug
Superhost
Room in The Blue Mountains
2nd Floor Room + Private balcony
4.79 out of 5 average rating, 76 reviews, 1 bed, 2 bathrooms
17–22 Aug