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Search results; Over 1,000 homes in Windsor

Top guest favourite
Serviced apartment in Windsor
New Studio Suite in Historic Gem
1 bedroom, 1 bed, 1 shared bathroom
28 Sept – 3 Oct
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4.92 out of 5 average rating, 83 reviews
Top guest favourite
Guest suite in Windsor
Dar's Dwelling - A suite place to stay.
1 bedroom, 1 queen bed, 1 bathroom
29 Sept – 4 Oct
4.93 out of 5 average rating, 196 reviews
Guest favourite
Guest suite in Windsor
Cozy Suite with Private Entrance
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.83 out of 5 average rating, 124 reviews
Top guest favourite
Flat in Windsor
Minutes to Wine Country- The Sunshine Suite
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.96 out of 5 average rating, 99 reviews
Top guest favourite
Cottage in Windsor
Knotty Pine Cottage - cozy lakeside getaway!
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 391 reviews
Top guest favourite
Flat in Windsor
Quiet Country 2 Bedroom Suite
2 bedrooms, 2 king beds, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 105 reviews
Guest favourite
Flat in Windsor
Renovated Studio Apartment, full amenities
1 king bed, 1 bathroom
1–6 Jan
4.9 out of 5 average rating, 103 reviews
Guest favourite
Apartment in Windsor
Quiet Downtown Apartment with Everything You Need
1 bedroom, 1 queen bed, 1 bathroom
1–6 Jan
4.96 out of 5 average rating, 129 reviews
Guest favourite
Cabin in Windsor
Private cabin on a lake - kayaks, SUP, fire pit
3 bedrooms, 4 beds, 1 bathroom
6–11 Nov
4.96 out of 5 average rating, 219 reviews
Top guest favourite
Cabin in Windsor
Hindy Hut with a hot tub
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 102 reviews
Dome in Windsor
StELLA – The Star Dome | Celestial Vineyard Escape
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
Top guest favourite
Cottage in Windsor
Birchwood on the Lake (with Hot Tub)
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 186 reviews
Top guest favourite
Cottage in Windsor
Falls Lake Burrow - 2 bdrm Cottage w/hot tub
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 152 reviews
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, 269 reviews
Guest favourite
Flat in Windsor
Gateway to Annapolis Valley | Windsor Studio Suite
1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.91 out of 5 average rating, 22 reviews
Top guest favourite
Cottage in Windsor
Wildberry Cottage
2 beds, 1 bathroom
29 Oct – 3 Nov
4.99 out of 5 average rating, 82 reviews
Top guest favourite
Home in Vaughan
Welcome to Piper's Perch - 10 Mins To The Ski Hill
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 68 reviews
Top guest favourite
Cabin in Newport
The Trapper's Cabin
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Wolfville
Lily's Pad
1 bedroom, 2 beds, 1 bathroom
31 Oct – 5 Nov
4.91 out of 5 average rating, 115 reviews