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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Guest house in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
1 bedroom, 3 beds, 1 private bathroom
10–15 Sept
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4.98 out of 5 average rating, 326 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, 261 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
24–29 Aug
5.0 out of 5 average rating, 119 reviews
Top 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, 215 reviews
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds, 4 bathrooms
21–26 Oct
4.98 out of 5 average rating, 86 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
8–13 Aug
4.98 out of 5 average rating, 56 reviews
Top guest favourite
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
2 bedrooms, 3 king beds, 2.5 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
4.98 out of 5 average rating, 182 reviews
Guest favourite
Treehouse in Occidental
The Spectacular Spyglass Treehouse
1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 362 reviews
Top guest favourite
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds, 2.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds, 4.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 94 reviews
Guest favourite
Home in Santa Rosa
Elegant & Spacious Luxury Wine Country Estate
4 bedrooms, 4 beds, 3 bathrooms
17–22 Aug
4.97 out of 5 average rating, 236 reviews
Top guest favourite
Home in Healdsburg
Heavenly Hideaway - Wine Tastings Included
2 bedrooms, 2 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
3 bedrooms, 3 queen beds, 2 bathrooms
23–28 Aug
4.98 out of 5 average rating, 44 reviews
Top guest favourite
Home in Santa Rosa
Donner Dos Wine Country Retreat
2 bedrooms, 2 queen beds, 3 bathrooms
20–25 Oct
5.0 out of 5 average rating, 33 reviews
Superhost
Home in Healdsburg
Wine Country Gem | Pool | Hot tub | BBQ
4 bedrooms, 7 beds, 3 bathrooms
22–27 Aug
4.95 out of 5 average rating, 64 reviews
Guest favourite
Home in Geyserville
Farmstay with Pool and Wine Tastings Included
3 bedrooms, 3 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Healdsburg
Healdsburg Luxe Reserve for 8, pool, spa, firepit
3 bedrooms, 4 beds, 3.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Santa Rosa
Sky View: Heated Pool & Hot Tub, 5 Acres
4 bedrooms, 5 beds, 4 bathrooms
9–14 Sept
4.99 out of 5 average rating, 70 reviews