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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, 263 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
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 56 reviews
Top guest favourite
Tiny home in Sebastopol
The Sonoma Spyglass | Incredible Views + Sauna
1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 217 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, 64 reviews
Guest favourite
Villa in Santa Rosa
Farmhouse Villa w/ Captivating Views & Hot Tub
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.98 out of 5 average rating, 128 reviews
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
4.98 out of 5 average rating, 182 reviews
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Nest
2 bedrooms, 2 beds, 1 bathroom
12–17 Aug
4.97 out of 5 average rating, 110 reviews
Top guest favourite
Guest house in Healdsburg
Designer Cottage | Garden Oasis | Walk to Plaza
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 254 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, 7 reviews
Guest favourite
Home in Healdsburg
ALBA | A modern luxury retreat in Healdsburg
2 bedrooms, 3 beds, 2 bathrooms
31 Aug – 5 Sept
4.96 out of 5 average rating, 25 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, 365 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
Top 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, 237 reviews
Guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 5 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, 71 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
12–17 Aug
Top guest favourite
Home in Healdsburg
Wine Country Estate: Pool, Spa & Vineyard Views
4 bedrooms, 6 beds, 4 bathrooms
14–19 Nov
4.98 out of 5 average rating, 86 reviews