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Search results; Over 1,000 homes in Windsor

Apartment in Windsor
1 BR Worldmark Windsor Resort Condo Wine Country
1 bedroom, 2 beds, 1 private bathroom
23–28 Jul
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Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds
25–30 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Room in Windsor
Rivermind, a Wine Country Retreat #1
1 queen bed
19–24 Jul
4.93 out of 5 average rating, 163 reviews
Guest favourite
Rooms in Windsor
Two-room suite for 1-4 guests
2 bedrooms, 2 queen beds
26–31 Jul
4.93 out of 5 average rating, 46 reviews
Apartment in Windsor
WorldMark Windsor Two-Bedroom Condo
2 bedrooms, 3 beds
8–13 Aug
4.37 out of 5 average rating, 51 reviews
Top guest favourite
Room in Windsor
Wine Country Stay
1 queen bed
26–31 Jul
4.9 out of 5 average rating, 210 reviews
Top guest favourite
Home in Windsor
Casa de la Esperanza: 1890s Gem - Hot Tub - 5BD/3BA
5 bedrooms, 6 beds
16–21 Jul
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Home in Windsor
Wine Country Retreat: Pool, Hot Tub, Views & EV
4 bedrooms, 6 beds
18–23 Jul
4.98 out of 5 average rating, 65 reviews
Guest favourite
Home in Windsor
Spacious Windsor Retreat | 4BR Home w/ Patio & BBQ
4 bedrooms, 5 beds
19–24 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Windsor
Gorgeous Victorian in the HEART of Windsor
3 bedrooms, 3 beds
22–27 Aug
4.99 out of 5 average rating, 132 reviews
Room in Windsor
Tranquil vineyard retreat
1 queen bed
19–24 Jul
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds
25–30 Oct
5.0 out of 5 average rating, 254 reviews
Home in Windsor
Adventures surround this charming 2bedroom home.
2 bedrooms, 5 beds
19–24 Jul
4.79 out of 5 average rating, 70 reviews
Top guest favourite
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
1 king bed
27 Oct – 1 Nov
4.97 out of 5 average rating, 690 reviews
Guest favourite
Home in Santa Rosa
Sonoma Wine Retreat | BBQ • 3 Ensuite Baths
3 bedrooms, 3 beds
19–24 Jul
4.93 out of 5 average rating, 259 reviews
Guest favourite
Home in Windsor
Winelight Vineyard Home With Spa
2 bedrooms, 2 beds
9–14 Aug
4.96 out of 5 average rating, 442 reviews
Superhost
Home in Santa Rosa
The Retreat at Mount Taylor, by Vinifera Homes
4 bedrooms, 5 beds
2–7 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Wine Retreat • Tasting Perks • FirePit
2 bedrooms, 3 beds
25–30 Oct
4.96 out of 5 average rating, 98 reviews
Top guest favourite
Home in Fulton
Wine Country Cottage Escape
2 bedrooms, 3 beds
16–21 Aug
4.96 out of 5 average rating, 97 reviews