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Search results; Over 1,000 homes in Hillsdale

Top guest favourite
Guest suite in Hillsdale
Country Get Away (Entire Private Lower Suite)
2 bedrooms, 3 beds, 1 private bathroom
23–28 Aug
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4.95 out of 5 average rating, 563 reviews
Superhost
Home in Hillsdale
Lost in Hillsdale | Heated POOL | Near Horseshoe
4 bedrooms, 4 beds, 2.5 bathrooms
17–22 Sept
4.76 out of 5 average rating, 29 reviews
Guest favourite
Tiny home in Waubaushene
Unique TinyHome
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.95 out of 5 average rating, 488 reviews
Guest favourite
Cabin in Elmvale
The Blue Cottage
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
4.89 out of 5 average rating, 46 reviews
Top guest favourite
Flat in Oro-Medonte
On the Fifth - Basement Apartment in the Country.
3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Coldwater
Fireside Haven Chalet
3 bedrooms, 4 beds, 3 bathrooms
16–21 Aug
4.99 out of 5 average rating, 72 reviews
Top guest favourite
Cottage in Elmvale
Lakefront Family-Friendly Cottage on Trails
2 bedrooms, 5 beds, 2 bathrooms
28 Aug – 2 Sept
4.98 out of 5 average rating, 53 reviews
Guest favourite
Home in Hillsdale
The four season Mount St. Louis hideaway
4 bedrooms, 5 beds, 3.5 bathrooms
16–21 Aug
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Barrie
Entire Luxury Townhouse | Barrie Hideaway
3 bedrooms, 4 beds, 1.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 63 reviews
Guest favourite
Guest suite in Oro-Medonte
The Suite at Bass Lake Retreat (Unit#4)
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 581 reviews
Top guest favourite
Cottage in Barrie
Minet's Point Beach House w/ Hot Tub & Beach
3 bedrooms, 4 beds, 3 bathrooms
15–20 Aug
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Tent in Orillia
Safari Tent on Horse Farm - sleeps 2-4
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 52 reviews
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, 24 reviews
Top guest favourite
Guest suite in Oro-Medonte
The Studio at Bass Lake Retreat (Unit #5)
1 queen bed, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 426 reviews
Guest favourite
Dome in Gravenhurst
Casa Doma | Unique 3BR Muskoka Retreat + Hot Tub
3 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 39 reviews
Guest favourite
Flat in Barrie
Hollywood Haven in downtown Barrie Ontario
2 bedrooms, 2 beds, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Guest house in Innisfil
PinesGuestHouse walk to lake 2bdrms
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 77 reviews
Home in Tiny
Lakeside Stunning Cottage - Private Beach - New
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
New place to stay
Guest favourite
Guest suite in Severn
Lake View Loft
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.91 out of 5 average rating, 100 reviews