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Search results; Over 1,000 homes in Windsor

Guest favourite
Apartment in Windsor
Sip, Taste, Hot Tub - Repeat - 2 Bdrm Condo-Slps 6
2 bedrooms, 4 beds, 2 private bathrooms
3–8 Aug
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4.89 out of 5 average rating, 57 reviews
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds, 2.5 bathrooms
23–28 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Room in Windsor
Rivermind, a Wine Country Retreat #1
1 queen bed, 1 bathroom
27 Jul – 1 Aug
4.93 out of 5 average rating, 164 reviews
Guest favourite
Rooms in Windsor
Two-room suite for 1-4 guests
2 bedrooms, 2 queen beds, 1 bathroom
26–31 Jul
4.94 out of 5 average rating, 48 reviews
Top guest favourite
Home in Windsor
Casa de la Esperanza: 1890s Gem - Hot Tub - 5BD/3BA
5 bedrooms, 6 beds, 3 bathrooms
2–7 Aug
5.0 out of 5 average rating, 77 reviews
Top guest favourite
Home in Windsor
Wine Country Retreat: Pool, Hot Tub, Views & EV
4 bedrooms, 6 beds, 3 bathrooms
17–22 Aug
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, 3 bathrooms
2–7 Aug
5.0 out of 5 average rating, 7 reviews
Apartment in Windsor
WorldMark Windsor Two-Bedroom Condo
2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
4.37 out of 5 average rating, 51 reviews
Top guest favourite
Home in Windsor
Gorgeous Victorian in the HEART of Windsor
3 bedrooms, 3 beds, 2 bathrooms
11–16 Aug
4.99 out of 5 average rating, 132 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 256 reviews
Top guest favourite
Room in Windsor
Wine Country Stay
1 queen bed, 1 bathroom
26–31 Jul
4.9 out of 5 average rating, 211 reviews
Guest favourite
Cottage in Healdsburg
Vineyard Cottage | Fire Pit | Wine Country
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.84 out of 5 average rating, 90 reviews
Home in Windsor
Adventures surround this charming 2bedroom home.
2 bedrooms, 5 beds, 2 bathrooms
26–31 Jul
4.79 out of 5 average rating, 71 reviews
Superhost
Home in Santa Rosa
The Retreat at Mount Taylor, by Vinifera Homes
4 bedrooms, 5 beds, 3 bathrooms
2–7 Aug
5.0 out of 5 average rating, 5 reviews
Flat in Windsor
Enjoy Wine Country
2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
2 bedrooms, 2 king beds, 2 bathrooms
9–14 Aug
4.94 out of 5 average rating, 195 reviews
Guest favourite
Home in Windsor
Winelight Vineyard Home With Spa
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 442 reviews
Guest favourite
Treehouse in Occidental
The Spectacular Spyglass Treehouse
1 bedroom, 1 bed, 1 bathroom
26–31 Aug
4.98 out of 5 average rating, 358 reviews
Guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 208 reviews