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Search results; Over 1,000 homes in Hillsdale

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Top guest favourite
Guest suite in Hillsdale
Country Get Away (Entire Private Lower Suite)
2 bedrooms, 3 beds, 1 private bathroom
18–23 Oct
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4.95 out of 5 average rating, 571 reviews
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Guest favourite
Home in Hillsdale
The four season Mount St. Louis hideaway
4 bedrooms, 5 beds, 3.5 bathrooms
20–25 Sept
4.9 out of 5 average rating, 21 reviews
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Top guest favourite
Cottage in Elmvale
Lakefront Family-Friendly Cottage on Trails
2 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 56 reviews
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Cottage in Barrie
The Guesthouse on the North Shore Trail
2 beds, 1 bathroom
3–8 Oct
4.75 out of 5 average rating, 496 reviews
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Home in Barrie
Sofi House in Barrie
5 bedrooms, 6 beds, 2.5 bathrooms
20–25 Sept
New place to stay
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Superhost
Home in Barrie
Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts
4 bedrooms, 5 beds, 2.5 bathrooms
29 Sept – 4 Oct
4.9 out of 5 average rating, 145 reviews
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Top guest favourite
Cottage in Wasaga Beach
Charming riverside cottage, B&B license
4 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 302 reviews
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Home in Port Mcnicoll
Steps From the Beach and Hiking Trails!
3 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.97 out of 5 average rating, 66 reviews
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Top guest favourite
Home in Oro-Medonte
Havenwood
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 26 reviews
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Guest favourite
Apartment in Shanty Bay
Romantic Country Getaway
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 107 reviews
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Top guest favourite
Flat in Oro-Medonte
On the Fifth - Basement Apartment in the Country.
3 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 46 reviews
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Top guest favourite
Flat in Innisfil
Sunrise to Sunset - Friday Harbour Penthouse
3 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 40 reviews
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Top guest favourite
Apartment in Oro
Pet-friendly, 1 BR condo in Horseshoe Valley
1 bedroom, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 208 reviews
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Guest favourite
Chalet in Moonstone
All Season Chalet, Mt St Louis Moonstone
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.89 out of 5 average rating, 223 reviews
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Home in Barrie
Stanley House
4 bedrooms, 4 queen beds, 3 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 124 reviews
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Guest favourite
Home in Minesing
Sleeps 14 Family Retreat Near Barrie & SnowValley
4 bedrooms, 7 beds, 3.5 bathrooms
20–25 Sept
4.87 out of 5 average rating, 142 reviews
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Apartment in Shanty Bay
Welcome to Horseshoe Haven
1 bedroom, 2 beds, 1.5 bathrooms
7–12 Oct
New place to stay
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Superhost
Cottage in Waubaushene
Waterfront Paradise on the Georgian Bay
5 bedrooms, 8 beds, 3 bathrooms
27 Sept – 2 Oct
4.84 out of 5 average rating, 191 reviews
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Superhost
Home in Barrie
Entire House, Private/Clean 5bdr 6 Beds/Sleeps 12
5 bedrooms, 5 queen beds, 2.5 bathrooms
11–16 Oct
4.79 out of 5 average rating, 183 reviews