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Search results; Over 1,000 homes in Grey Highlands

Top guest favourite
Cottage in Grey Highlands
Hilltop garden cottage
3 bedrooms, 6 beds, 2 private bathrooms
16–21 Aug
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4.93 out of 5 average rating, 187 reviews
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
Yurt in Meaford
Quiet Retreat for Two
5.0 out of 5 average rating, 200 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Sept
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
Guest favourite
Home in Grey Highlands
Rosewood Parlour AFrame - by The Post Office Motel
4.98 out of 5 average rating, 45 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
Flat in Markdale
Dee’s Hideaway
4.95 out of 5 average rating, 37 reviews, 1 bedroom, 2 beds, 1 bathroom
26–31 Jul
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
Guest favourite
Guest suite in Kimberley
The Post Office Motel & Spa in the ❤️ of Kimberley
4.94 out of 5 average rating, 839 reviews, 1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Cabin in Kimberley
Kimberley Creek Cabin
4.98 out of 5 average rating, 420 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
18–23 Sept
Guest favourite
Cottage in Flesherton
Modern all-season cottage overlooking Lake Eugenia
4.95 out of 5 average rating, 101 reviews, 3 bedrooms, 4 beds, 1 bathroom
9–14 Aug
Top guest favourite
Cabin in Kimberley
Private Luxury Creekside Cabin with Sauna
4.99 out of 5 average rating, 100 reviews, 1 bedroom, 2 beds, 1 bathroom
21–27 Sept
Home in Grey Highlands
*Lake House Escape* 4 BR Family Cottage on Water
New place to stay, 4 bedrooms, 5 beds, 2 bathrooms
21–26 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
Top guest favourite
Cottage in Kimberley
Cozy Summer Getaway | Hot Tub Sauna BBQ & Firepit
4.89 out of 5 average rating, 128 reviews, 5 bedrooms, 10 beds, 2.5 bathrooms
9–14 Aug
Guest favourite
Home in Collingwood
The Light House
4.92 out of 5 average rating, 13 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
Home in Flesherton
Luxury Lakefront Log Retreat On 100 Acres
4.82 out of 5 average rating, 11 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
9–14 Aug
Home in Singhampton
Blue Mountain Riverside Lodge | Hottub & Sauna
4.86 out of 5 average rating, 58 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Aug
Top guest favourite
Flat in The Blue Mountains
Studio at Blue-KingBed/Pool/HotTub/Shuttle
4.96 out of 5 average rating, 395 reviews, 1 bedroom, 2 beds, 1 bathroom
3–8 Aug