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Search results; Over 1,000 homes in Windsor

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Top guest favourite
Flat in Windsor
Pool + 4 Hot Tubs! Gym, Luxury 2 bedroom villa.
2 bedrooms, 4 beds, 2 private bathrooms
2–7 Oct
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4.97 out of 5 average rating, 113 reviews
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Apartment in Windsor
WorldMark Windsor Two-Bedroom Condo
2 bedrooms, 3 beds, 2 bathrooms
19–24 Sept
4.4 out of 5 average rating, 53 reviews
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Resort in Windsor
Beautiful Windsor Resort - Spacious 1 Bedroom Unit
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.82 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Windsor
Pink kitchen • karaoke lounge • hot tub • walkable
3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 9 reviews
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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, 135 reviews
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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
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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
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Top guest favourite
Room in Windsor
Wine Country Stay
1 queen bed, 1 bathroom
19–24 Sept
4.9 out of 5 average rating, 214 reviews
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Top guest favourite
Home in Windsor
Wine Country Retreat: Pool, Hot Tub, Views & EV
4 bedrooms, 6 beds, 3 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 73 reviews
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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
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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, 105 reviews
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Guest favourite
Room in Windsor
Rivermind, a Wine Country Retreat #1
1 queen bed, 1 bathroom
5–10 Oct
4.93 out of 5 average rating, 171 reviews
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Guest favourite
Flat in Windsor
Windsor/Sonoma 2 Bed/2 Bath Condo Resort ~ Pool ~
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.89 out of 5 average rating, 73 reviews
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Top guest favourite
Home in Healdsburg
Vineyard View Retreat • Fire Pit • Wine Perks
2 bedrooms, 3 beds, 2 bathrooms
16–21 Nov
4.96 out of 5 average rating, 98 reviews
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Resort in Windsor
A Cozy Studio unit in Beautiful CA Wine Country!
1 queen bed, 1 bathroom
20–25 Sept
4.78 out of 5 average rating, 9 reviews
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Flat in Windsor
Windsor Resort Getaway
2 bedrooms, 3 beds, 2 bathrooms
31 Oct – 5 Nov
New place to stay
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Guest favourite
Flat in Windsor
Wine Country 2 Bedroom Sleeps 6!
2 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Santa Rosa
Elegant & Spacious Luxury Wine Country Estate
4 bedrooms, 4 beds, 3 bathrooms
28 Nov – 3 Dec
4.97 out of 5 average rating, 244 reviews
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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