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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 beds, 1.5 private bathrooms
25–30 Oct
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5.0 out of 5 average rating, 257 reviews
Superhost
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
5.0 out of 5 average rating, 3 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, 42 reviews
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
4.98 out of 5 average rating, 181 reviews
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
1 bedroom, 1 bed, 1 bathroom
3–8 Aug
4.98 out of 5 average rating, 56 reviews
Top guest favourite
Home in Healdsburg
Cuvée House
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
6 bedrooms, 7 beds, 3.5 bathrooms
11–16 Aug
5.0 out of 5 average rating, 29 reviews
Home in St. Helena
Hidden Hills Napa Retreat | St. Helena Gem
4 bedrooms, 6 beds, 5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4 bedrooms, 5 beds, 4 bathrooms
23–28 Aug
4.97 out of 5 average rating, 117 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, 118 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
Top guest favourite
Home in Healdsburg
WC Oasis with Hot Tub - Wine Tastings Included
4 bedrooms, 5 beds, 4 bathrooms
15–20 Aug
4.95 out of 5 average rating, 62 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, 208 reviews
Top guest favourite
Guest house in Healdsburg
Healdsburg Designer Cottage | Walk to Plaza
1 bedroom, 2 beds, 1 bathroom
4–9 Aug
4.97 out of 5 average rating, 253 reviews
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
4.99 out of 5 average rating, 127 reviews
Top guest favourite
Home in Healdsburg
Downtown Healdsburg Plaza Charmer + Hot Tub
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 72 reviews
Guest favourite
Home in Healdsburg
Healdsburg Plaza Gem-Hot Tub and Tastings Included
2 bedrooms, 2 queen beds, 2 bathrooms
3–8 Aug
4.9 out of 5 average rating, 92 reviews
Top guest favourite
Home in Geyserville
Doxie Ranch - Serene Vineyard Escape
3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Healdsburg
Dreamy A-Frame Luxury - Privacy -Views-Hot Tub
5 bedrooms, 7 beds, 4 bathrooms
2–7 Aug
4.92 out of 5 average rating, 48 reviews