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Search results; Over 1,000 homes in Windsor

Guest favourite
Flat in Windsor
Windsor/Sonoma 2 Bed/2 Bath Condo Resort ~ Pool ~
2 bedrooms, 3 beds, 2 private bathrooms
27 Sept – 2 Oct
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4.89 out of 5 average rating, 73 reviews
Apartment in Windsor
WorldMark Windsor Two-Bedroom Condo
2 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
4.4 out of 5 average rating, 53 reviews
Top guest favourite
Home in Windsor
Pink kitchen • karaoke lounge • hot tub • walkable
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Sept
5.0 out of 5 average rating, 9 reviews
Room in Windsor
Beautiful Windsor Resort - Spacious 1 Bedroom Unit
2 beds, 1 bathroom
4–9 Oct
4.82 out of 5 average rating, 11 reviews
Top guest favourite
Home in Windsor
Casa de la Esperanza: 1890s Gem - Hot Tub
5 bedrooms, 6 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 81 reviews
Top guest favourite
Home in Windsor
Gorgeous Victorian in the HEART of Windsor
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 134 reviews
Guest favourite
Rooms in Windsor
Two-room suite for 1-4 guests
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
4.93 out of 5 average rating, 54 reviews
Top guest favourite
Home in Windsor
Wine Country Retreat: Pool, Hot Tub, Views & EV
4 bedrooms, 6 beds, 3 bathrooms
21–26 Sept
4.99 out of 5 average rating, 71 reviews
Flat in Windsor
Enjoy Wine Country
2 bedrooms, 1 queen bed, 2 bathrooms
20–25 Sept
Top guest favourite
Room in Windsor
Wine Country Stay
1 queen bed, 1 bathroom
9–14 Sept
4.9 out of 5 average rating, 214 reviews
Guest favourite
Room in Windsor
Rivermind, a Wine Country Retreat #1
1 queen bed, 1 bathroom
9–14 Sept
4.93 out of 5 average rating, 170 reviews
Guest favourite
Townhouse in Windsor
Wine and Golf Paradise in Windsor, CA (#1)
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.88 out of 5 average rating, 104 reviews
Superhost
Home in Windsor
Wine Country Escape | Hot Tub & Fire Pit
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
Top guest favourite
Home in Windsor
Winelight Vineyard Home With Spa
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 445 reviews
Home in Windsor
Adventures surround this charming 2bedroom home.
2 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.77 out of 5 average rating, 75 reviews
Guest favourite
Home in Windsor
Gourmet Kitchen in Wine Country w/Hot Tub + Office
4 bedrooms, 7 beds, 2.5 bathrooms
21–26 Sept
4.95 out of 5 average rating, 116 reviews
Guest favourite
Flat in Windsor
Wine Country 2 Bedroom Sleeps 6!
2 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.95 out of 5 average rating, 96 reviews
Guest favourite
Home in Windsor
Spacious Windsor Retreat | 4BR Home w/ Patio & BBQ
4 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms, 7 beds, 3 bathrooms
18–23 Sept
4.95 out of 5 average rating, 66 reviews