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Search results; Over 1,000 homes in Annan

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Guest favourite
Cottage in Annan
Private 5 Acres Lakefront Cottage - Georgian Bay
4 bedrooms, 4 beds, 3 private bathrooms
11–16 Oct
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4.94 out of 5 average rating, 82 reviews
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Cottage in Meaford
Cosy and modern cottage on beautiful Georgian Bay
3 bedrooms, 4 beds, 1 bathroom
18–23 Oct
4.91 out of 5 average rating, 220 reviews
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Home in Annan
Highland House Retreat- Luxury Log Home
5 bedrooms, 6 beds, 2.5 bathrooms
24–29 Nov
4.99 out of 5 average rating, 88 reviews
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Home in Meaford
The Velvet Pier by the Post Office Motel *HOT TUB*
4 bedrooms, 4 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 7 reviews
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Cottage in Kemble
Georgian Bay Waterfront Oasis
2 bedrooms, 4 beds, 1 bathroom
29 Sept – 4 Oct
4.85 out of 5 average rating, 192 reviews
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Guest house in Wiarton
Stunning Lakeside Loft Perched Above Georgian Bay
4 bedrooms, 5 beds, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 131 reviews
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Flat in Owen Sound
Private Suite • Near Bruce Trail • Modern & Bright
1 bedroom, 1 queen bed, 1 bathroom
23–28 Oct
4.98 out of 5 average rating, 154 reviews
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Cabin in Shallow Lake
Privacy Plus - cozy two bedroom country cottage
2 bedrooms, 4 beds, 1.5 bathrooms
19–24 Oct
4.97 out of 5 average rating, 61 reviews
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Flat in Owen Sound
East Side Serenity Apartment
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.94 out of 5 average rating, 340 reviews
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Home in Kemble
Luxury 5BR Home w/ Fire Pit near Georgian Bay
5 bedrooms, 9 beds, 3 bathrooms
12–17 Oct
4.91 out of 5 average rating, 79 reviews
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Guest house in Kemble
Waterfront Sunrise Cottage
1 bedroom, 2 beds, 1 bathroom
28 Sept – 3 Oct
4.86 out of 5 average rating, 229 reviews
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Guest favourite
Cottage in Meaford
The SURF SHACK by The Post Office Motel *HOT TUB*
3 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.77 out of 5 average rating, 636 reviews
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Flat in Owen Sound
One bedroom apartment on the river, with hot tub
1 bedroom, 1 queen bed, 1 bathroom
5–10 Oct
4.86 out of 5 average rating, 146 reviews
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Home in Meaford
Quaint country cottage by the Bay
3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Sept
4.77 out of 5 average rating, 95 reviews
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Cottage in Wiarton
A cabin disconnect on Boat Lake - pet friendly
2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
4.98 out of 5 average rating, 40 reviews
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Chalet in Meaford
Sundance of Blantyre Lodge +Hot Tub +Sauna +Pond
7 bedrooms, 9 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 138 reviews
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Cabin in Owen Sound
Heritage Reflections Guest House
1 bedroom, 2 beds, 1 bathroom
8–13 Dec
4.88 out of 5 average rating, 352 reviews
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Flat in Owen Sound
Cozy Hideaway
2 bedrooms, 4 beds, 1 bathroom
16–21 Oct
4.9 out of 5 average rating, 350 reviews
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Guest suite in Meaford
The Beach Button
1 bedroom, 1 bed, 1 bathroom
25–30 Oct
4.93 out of 5 average rating, 362 reviews