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Search results; Over 1,000 homes in Windsor

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Top guest favourite
Cottage in Windsor
Wildberry Cottage
Studio, 2 beds, 1 private bathroom
23–28 Oct
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4.98 out of 5 average rating, 89 reviews
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Top guest favourite
Serviced apartment in Windsor
New Studio Suite in Historic Gem
1 bedroom, 1 bed, 1 bathroom
1–6 Oct
4.92 out of 5 average rating, 86 reviews
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Top guest favourite
Guest suite in Windsor
Dar's Dwelling - A suite place to stay.
1 bedroom, 1 queen bed, 1 bathroom
13–18 Oct
4.94 out of 5 average rating, 202 reviews
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Top guest favourite
Home in Windsor
Mounce Mansion - Country House-Sleeps 12+
5 bedrooms, 7 beds, 2.5 bathrooms
1–6 Oct
4.98 out of 5 average rating, 101 reviews
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Top guest favourite
Flat in Windsor
Minutes to Wine Country- The Sunshine Suite
1 bedroom, 1 queen bed, 1 bathroom
13–18 Oct
4.96 out of 5 average rating, 100 reviews
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Top guest favourite
Chalet in Windsor
Rocky Brook Chalet
4 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
4.96 out of 5 average rating, 271 reviews
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Guest suite in Windsor
Cozy Suite with Private Entrance
1 bedroom, 1 queen bed, 1 bathroom
13–18 Oct
4.82 out of 5 average rating, 127 reviews
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Top guest favourite
Cottage in Windsor
Knotty Pine Cottage - cozy lakeside getaway!
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
4.92 out of 5 average rating, 396 reviews
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Top guest favourite
Cabin in Newport
The Trapper's Cabin
2 bedrooms, 3 beds, 1 bathroom
20–25 Oct
4.94 out of 5 average rating, 17 reviews
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Top guest favourite
Cottage in Windsor
Birchwood on the Lake (with Hot Tub)
3 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.99 out of 5 average rating, 189 reviews
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Top guest favourite
Flat in Windsor
Gateway to Annapolis Valley | Windsor Studio Suite
1 queen bed, 1 bathroom
4–9 Oct
4.94 out of 5 average rating, 31 reviews
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Guest favourite
Flat in Windsor
Stylish Windsor Suite Near Wineries & Fundy Coast
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
4.9 out of 5 average rating, 10 reviews
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Guest favourite
Cabin in Windsor
Private cabin on a lake - kayaks, SUP, fire pit
3 bedrooms, 4 beds, 1 bathroom
9–14 Nov
4.96 out of 5 average rating, 224 reviews
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Top guest favourite
Cabin in Windsor
Hindy Hut with a hot tub
3 bedrooms, 4 beds, 1 bathroom
25–30 Oct
4.93 out of 5 average rating, 107 reviews
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Dome in Windsor
LUNA – The Moon Dome | A Romantic Vineyard Escape
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Cottage in Windsor
Falls Lake Burrow - 2 bdrm Cottage w/hot tub
2 bedrooms, 3 beds, 1 bathroom
5–10 Oct
4.97 out of 5 average rating, 153 reviews
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Guest favourite
Apartment in Windsor
Quiet Downtown Apartment with Everything You Need
1 bedroom, 1 queen bed, 1 bathroom
1–6 Jan
4.95 out of 5 average rating, 130 reviews
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Guest favourite
Cabin in Windsor
All Decked Out
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Oct
4.94 out of 5 average rating, 83 reviews
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Dome in Windsor
StELLA – The Star Dome | Celestial Vineyard Escape
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 4 reviews