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Search results; Over 1,000 homes in Windsor

Descriptions are based on details hosts provide
Top guest favourite
Chalet in Windsor
Rocky Brook Chalet
4 bedrooms, 5 beds, 2 private bathrooms
18–23 Oct
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4.96 out of 5 average rating, 262 reviews
Top guest favourite
Guest suite in Windsor
Dar's Dwelling - A suite place to stay.
4.93 out of 5 average rating, 190 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Aug
Top guest favourite
Serviced apartment in Windsor
Mid-century modern in a historic building
4.9 out of 5 average rating, 73 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Sept
Superhost
Home in Windsor
The Martock House · Ski-Inspired Sauna Retreat
4.84 out of 5 average rating, 45 reviews, 2 bedrooms, 4 beds, 1 bathroom
23–28 Aug
Guest favourite
Apartment in Windsor
Newly built downtown, near wineries
4.96 out of 5 average rating, 119 reviews, 1 bedroom, 1 bed, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Home in Windsor
Mounce Mansion - Country House-Sleeps 12+
4.98 out of 5 average rating, 98 reviews, 5 bedrooms, 7 beds, 2.5 bathrooms
1–6 Jun
Guest favourite
Flat in Windsor
Fully renovated with a gated courtyard
4.9 out of 5 average rating, 92 reviews, 1 bed, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Flat in Windsor
Quiet Country 2 Bedroom Suite
5.0 out of 5 average rating, 99 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Sept – 4 Oct
Guest favourite
Guest suite in Windsor
Cozy Suite with Private Entrance
4.84 out of 5 average rating, 121 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Sept
Guest favourite
Cottage in Windsor
Lakefront with a dock and sandy beach
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 5 beds, 2 bathrooms
26–31 Oct
Guest favourite
Cabin in Windsor
Private cabin on a lake - kayaks, SUP, fire pit
4.97 out of 5 average rating, 213 reviews, 3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Windsor
Lakeside with a private dock and deck
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Cottage in Windsor
Knotty Pine Cottage - cozy lakeside getaway!
4.92 out of 5 average rating, 384 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Oct
Cabin in Newport
Private cabin beside a quiet pond
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
Guest favourite
Flat in Windsor
Minutes to Wine Country- The Sunshine Suite
4.96 out of 5 average rating, 93 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Top guest favourite
Cottage in Windsor
Birchwood on the Lake (with Hot Tub)
4.99 out of 5 average rating, 185 reviews, 3 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
Superhost
Flat in Windsor
Newly renovated and minutes from wineries
1 bedroom, 1 bed, 1 bathroom
19–24 Aug
Top guest favourite
Cottage in Windsor
Wildberry Cottage
4.99 out of 5 average rating, 69 reviews, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Flat in Hantsport
Century home with a private outdoor sauna
5.0 out of 5 average rating, 176 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Oct