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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, 256 reviews
Top guest favourite
Guest house in Healdsburg
Healdsburg Designer Cottage | Walk to Plaza
4.97 out of 5 average rating, 253 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Flat in Healdsburg
Downtown Healdsburg Perch
4.98 out of 5 average rating, 56 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
4.98 out of 5 average rating, 181 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Home in Healdsburg
WC Oasis with Hot Tub - Wine Tastings Included
4.95 out of 5 average rating, 62 reviews, 4 bedrooms, 5 beds, 4 bathrooms
15–20 Aug
Top guest favourite
Home in Healdsburg
Cuvée House
5.0 out of 5 average rating, 50 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Home in St. Helena
Hidden Hills Napa Retreat | St. Helena Gem
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 6 beds, 5 bathrooms
9–14 Aug
Top guest favourite
Home in Healdsburg
Vintage Retreat with Spa in Healdsburg
4.98 out of 5 average rating, 41 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Room in Santa Rosa
Golf Course Sanctuary-Designed for Travel Nurses
New place to stay, 1 queen bed, 1 bathroom
1–6 Aug
Superhost
Home in Healdsburg
The Grove on Alexander Valley
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Luxe
Home in Healdsburg
Country Retreat With Pool And More
4.97 out of 5 average rating, 117 reviews, 4 bedrooms, 5 beds, 4 bathrooms
23–28 Aug
Guest favourite
Home in Forestville
Somms Rest Designed Curated Peaceful
4.99 out of 5 average rating, 368 reviews, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
Guest favourite
Holiday home in Healdsburg
Downtown Healdsburg Nest
4.97 out of 5 average rating, 109 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Guest favourite
Home in Healdsburg
Casa Chiquita - Coziest in town!
4.97 out of 5 average rating, 104 reviews, 3 bedrooms, 3 beds, 3 bathrooms
20–25 Aug
Top guest favourite
Home in Healdsburg
Downtown Healdsburg Plaza Charmer + Hot Tub
4.99 out of 5 average rating, 72 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Guest favourite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
5.0 out of 5 average rating, 66 reviews, 3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Santa Rosa
Donner Dos Wine Country Retreat
5.0 out of 5 average rating, 32 reviews, 2 bedrooms, 2 beds, 3 bathrooms
15–20 Sept
Top guest favourite
Home in Healdsburg
Private Oasis in Healdsburg: Pool, Spa & Views
5.0 out of 5 average rating, 29 reviews, 6 bedrooms, 7 beds, 3.5 bathrooms
11–16 Aug
Top guest favourite
Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
4.92 out of 5 average rating, 131 reviews, 3 bedrooms, 4 beds, 2 bathrooms
11–16 Sept