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Search results; Over 1,000 homes in Windsor

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Superhost

Apartment in Windsor

Sip, Taste, Hot Tub - Repeat - 2 Bdrm Condo-Slps 6

2 bedrooms, 4 beds, 2 private bathrooms

4–9 Oct

$1,798 SGD for 5 nights

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4.9 out of 5 average rating, 59 reviews

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Apartment in Windsor

WorldMark Windsor Two-Bedroom Condo

2 bedrooms, 3 beds

1–6 Oct

Extended stay discount

4.41 out of 5 average rating, 54 reviews

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Top guest favourite

Home in Windsor

Casa de la Esperanza:1890s Gem - Hot Tub

5 bedrooms, 6 beds

1–6 Oct

$4,356 SGD for 5 nights

5.0 out of 5 average rating, 83 reviews

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Superhost

Home in Windsor

Wine Country Escape | Hot Tub & Fire Pit

3 bedrooms, 7 beds

25–30 Oct

$2,946 SGD for 5 nights

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Top guest favourite

Home in Windsor

Pink kitchen • karaoke lounge • hot tub • walkable

3 bedrooms, 3 beds

12–17 Oct

$3,521 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 10 reviews

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Guest favourite

Rooms in Windsor

Two-room suite for 1-4 guests

2 bedrooms, 2 queen beds

25–30 Oct

$965 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 55 reviews

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Top guest favourite

Home in Windsor

Wine Country Retreat: Pool, Hot Tub, Views & EV

4 bedrooms, 6 beds

4–9 Oct

4.99 out of 5 average rating, 73 reviews

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Top guest favourite

Room in Windsor

Wine Country Stay

1 queen bed

5–10 Oct

$602 SGD for 5 nights

Free cancellation

4.9 out of 5 average rating, 214 reviews

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Top guest favourite

Home in Windsor

Gorgeous Victorian in the HEART of Windsor

3 bedrooms, 3 beds

16–21 Nov

$3,183 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 135 reviews

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Guest favourite

Townhouse in Windsor

Wine and Golf Paradise in Windsor, CA (#2)

2 bedrooms, 3 beds

11–16 Oct

$1,609 SGD for 5 nights

4.93 out of 5 average rating, 80 reviews

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Resort in Windsor

Beautiful Windsor Resort - Spacious 1 Bedroom Unit

1 bedroom, 2 beds

26–31 Oct

$970 SGD for 5 nights

4.82 out of 5 average rating, 11 reviews

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Guest favourite

Home in Windsor

Gourmet Kitchen in Wine Country w/Hot Tub + Office

4 bedrooms, 7 beds

4–9 Oct

$7,820 SGD for 5 nights

4.95 out of 5 average rating, 116 reviews

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Flat in Windsor

Windsor 2BR Condo | Sonoma Wine Country

2 bedrooms, 3 beds

1–6 Oct

New place to stay

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Guest favourite

Serviced apartment in Windsor

Windsor/Sonoma 2 Bed/2 Bath Condo Resort~Pool~

2 bedrooms, 3 beds

30 Oct – 4 Nov

$1,585 SGD for 5 nights

4.89 out of 5 average rating, 73 reviews

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Flat in Windsor

Windsor 2BR Resort Condo Near Sonoma Wineries

2 bedrooms, 3 beds

4–9 Oct

New place to stay

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Home in Windsor

Adventures surround this charming 2bedroom home.

2 bedrooms, 5 beds

4–9 Oct

$1,619 SGD for 5 nights

4.77 out of 5 average rating, 75 reviews

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Guest favourite

Apartment in Windsor

Great Wine Country and Golfing Resort Getaway!

2 bedrooms, 4 beds

24–29 Dec

$2,335 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 98 reviews

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Guest favourite

Home in Healdsburg

Healdsburg Farmhouse. Pool, spa, BBQ. Sleeps 10

4 bedrooms, 7 beds

1–6 Oct

4.88 out of 5 average rating, 24 reviews

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Guest favourite

Home in Santa Rosa

Sonoma Wine Country Retreat | 3 Ensuite Baths

3 bedrooms, 3 beds

2–7 Oct

$2,808 SGD for 5 nights

4.94 out of 5 average rating, 270 reviews