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Search results; Over 1,000 homes in Windsor

Top guest favourite
Home in Windsor
Timberline Retreat - Great for teams & families!
3 bedrooms, 7 beds, 2.5 private bathrooms
13–18 Sept
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5.0 out of 5 average rating, 54 reviews
Top guest favourite
Guest house in Windsor
Walk to Lake, Restaurants, & Pickleball.
1 bed, 1 bathroom
24–29 Sept
5.0 out of 5 average rating, 120 reviews
Top guest favourite
Home in Windsor
The Windsor Exchange Retreat
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Room in Windsor
Cozy Windsor Queen Guest Bedroom #2
1 queen bed, 1 bathroom
5–10 Oct
4.96 out of 5 average rating, 26 reviews
Guest favourite
Guest suite in Windsor
Swanky Downtown Getaway!
2 bedrooms, 2 beds, 1 bathroom
9–14 Jan
4.93 out of 5 average rating, 235 reviews
Top guest favourite
Home in Windsor
King size bed! 5-Bedroom Home W/ Outdoor Pergola!
5 bedrooms, 6 beds, 2 bathrooms
27 Nov – 2 Dec
4.95 out of 5 average rating, 169 reviews
Guest favourite
Room in Windsor
Comfortable & beautiful house
1 bed, 1 bathroom
11–16 Sept
4.84 out of 5 average rating, 83 reviews
Guest favourite
Home in Windsor
Windsor Getaway
4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Oct
4.91 out of 5 average rating, 86 reviews
Top guest favourite
Flat in Windsor
Lake Life on Birch ~ Boardwalk Park
2 bedrooms, 2 beds, 1.5 bathrooms
22–27 Sept
4.95 out of 5 average rating, 126 reviews
Guest favourite
Home in Windsor
Windsor Peaceful Escape!
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.82 out of 5 average rating, 56 reviews
Guest favourite
Guest suite in Windsor
Cheerful Pet-Friendly Lower Level Stay
2 bedrooms, 12 beds, 1 bathroom
15–20 Sept
4.9 out of 5 average rating, 31 reviews
Top guest favourite
Guest suite in Windsor
Guest Suite
1 bedroom, 1 bed, 1 bathroom
26 Sept – 1 Oct
4.97 out of 5 average rating, 63 reviews
Top guest favourite
Guest suite in Windsor
The Studio: A Mid Century Style Guest House
1 bedroom, 1 king bed, 1 bathroom
21–26 Sept
4.97 out of 5 average rating, 190 reviews
Superhost
Guest suite in Windsor
Neighborhood Nest
3 bedrooms, 3 queen beds, 1 bathroom
13–18 Sept
4.89 out of 5 average rating, 54 reviews
Guest favourite
Home in Windsor
Quaint three-bedroom house
3 bedrooms, 3 queen beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Guest house in Windsor
Ranch Retreat
1 bedroom, 2 beds, 1 bathroom
13–18 Oct
4.98 out of 5 average rating, 94 reviews
Top guest favourite
Home in Windsor
Quiet peaceful home near Chimney Park
3 bedrooms, 3 beds, 2 bathrooms
22–27 Oct
4.94 out of 5 average rating, 202 reviews
Top guest favourite
Room in Windsor
Private room in our quiet home - no chores!
1 queen bed, 1 bathroom
15–20 Sept
4.95 out of 5 average rating, 86 reviews
Top guest favourite
Home in Windsor
Courtside Estates • Luxury Stay w/ Pickleball
7 bedrooms, 12 beds, 5 bathrooms
22–27 Sept
4.95 out of 5 average rating, 22 reviews