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Search results; Over 1,000 homes in Annan

Guest favourite
Cottage in Annan
Private 5 Acres Lakefront Cottage - Georgian Bay
4 bedrooms, 4 beds, 3 private bathrooms
29 Aug – 3 Sept
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4.95 out of 5 average rating, 77 reviews
Guest favourite
Cottage in Meaford
Cosy and modern cottage on beautiful Georgian Bay
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 215 reviews
Guest favourite
Home in Annan
The Sixth Great Lake Luxury
4 bedrooms, 6 beds, 3.5 bathrooms
27 Aug – 1 Sept
4.9 out of 5 average rating, 39 reviews
Guest favourite
Home in Meaford
Beach House Hideaway by Post Office Motel *HOT TUB
3 bedrooms, 3 queen beds, 1 bathroom
4–9 Sept
4.87 out of 5 average rating, 542 reviews
Top guest favourite
Home in South Bruce Peninsula
Pine Villa-Mediterranean Cottage with Hot Tub
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 112 reviews
Home in South Bruce Peninsula
Wiarton Home Waterview Bruce Peninsula EV Charger
3 bedrooms, 6 beds, 2 bathrooms
7–12 Sept
New place to stay
Top guest favourite
Guest house in Wiarton
Bruce Peninsula Country Loft on 17
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 240 reviews
Guest favourite
Home in Owen Sound
Balmy Beach Breeze Waterfront Home
3 bedrooms, 8 beds, 1.5 bathrooms
8–13 Sept
4.88 out of 5 average rating, 94 reviews
Guest favourite
Tiny home in Meaford
Tiny Home Nestled between Thornbury & Meaford
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.86 out of 5 average rating, 440 reviews
Guest favourite
Home in Kemble
*NEW Luxury Cobble Beach Golf Retreat w/ Game Room
5 bedrooms, 6 beds, 4 bathrooms
16–21 Aug
4.89 out of 5 average rating, 9 reviews
Guest favourite
Bed and breakfast in Owen Sound
Micha’s Bed & Breakfast - Paris Room (2-3)
1 bedroom, 1 king bed, 1.5 bathrooms
16–21 Aug
4.96 out of 5 average rating, 201 reviews
Top guest favourite
Cottage in Southgate
Luxurious Creek Retreat With Hot Tub
2 bedrooms, 2 beds, 1 bathroom
2–7 Nov
4.99 out of 5 average rating, 182 reviews
Guest favourite
Cabin in Meaford
Minniehill A-Frame
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.92 out of 5 average rating, 177 reviews
Top guest favourite
Cottage in Meaford
"Blue Vue" Georgian Bay Waterfront Cottage
4 bedrooms, 4 queen beds, 2.5 bathrooms
27 Sept – 2 Oct
4.92 out of 5 average rating, 107 reviews
Luxe
Cottage in Meaford
Bayview Oasis: Luxe Lakeside Escape w/ Pickleball
4 bedrooms, 8 beds, 3 bathrooms
31 Aug – 5 Sept
4.97 out of 5 average rating, 126 reviews
Guest favourite
Guest house in Kemble
Waterfront Sunrise Cottage
1 bedroom, 2 beds, 1 bathroom
21–26 Sept
4.87 out of 5 average rating, 225 reviews
Top guest favourite
Cabin in Wiarton
Fika North | Slow Mornings & Summer Nights
3 bedrooms, 4 beds, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Chalet in Meaford
Sundance of Blantyre Lodge +Hot Tub +Sauna +Pond
7 bedrooms, 9 beds, 3.5 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 133 reviews
Top guest favourite
Camper van/Motorhome in Annan
Base Camp Glamping Grey Bruce
2 bedrooms, 3 beds, 1 bathroom
1–6 Jan
4.96 out of 5 average rating, 24 reviews