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Search results; Over 1,000 homes in Healdsburg

Guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Orchard Suite
3 bedrooms, 3 beds, 3 private bathrooms
12–17 Sept
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4.94 out of 5 average rating, 47 reviews
Featured hotel
Hotel in Healdsburg
Healdsburg king
1 bedroom, 1 king bed, 1 bathroom
27 Nov – 2 Dec
Top guest favourite
Home in Healdsburg
Wake Up at Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.98 out of 5 average rating, 183 reviews
Top guest favourite
Home in Healdsburg
Healdsburg House - Chiquita Road
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 124 reviews
Home in Healdsburg
Montage Resort Healdsburg Harvest Home Rental
4 bedrooms, 4 beds, 4 bathrooms
9–14 Sept
Luxe
Home in Healdsburg
3 BR | Saltwater Pool | Spa | Walk to Wineries
3 bedrooms, 6 beds, 4 bathrooms
25–30 Oct
5.0 out of 5 average rating, 42 reviews
Home in Healdsburg
Wine Country Oasis with Pool, Bocce, Pickleball
4 bedrooms, 8 beds, 3.5 bathrooms
21–26 Sept
New place to stay
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, 272 reviews
Top guest favourite
Home in Healdsburg
Ivy House Healdsburg @Ivyhousehealdsburg
2 bedrooms, 2 beds, 1.5 bathrooms
15–20 Oct
4.99 out of 5 average rating, 72 reviews
Luxe
Villa in Healdsburg
New! The Quails Crossing- Healdsburg Vineyard Home
4 bedrooms, 4 beds, 4.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 96 reviews
Top guest favourite
Home in Healdsburg
The Grove on Alexander Valley
3 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 6 reviews
Guest favourite
Villa in Healdsburg
Trinite Estate
5 bedrooms, 6 beds, 4.5 bathrooms
10–15 Sept
4.91 out of 5 average rating, 176 reviews
Top guest favourite
Home in Healdsburg
Large Outdoor Kitchen, Pool, Hot Tub, Firepit
4 bedrooms, 7 beds, 3.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 106 reviews
Guest favourite
Home in Healdsburg
The Healdsburg Haven
4 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
5.0 out of 5 average rating, 40 reviews
Guest favourite
Home in Healdsburg
Haven at Healdsburg, by Vinifera Homes
3 bedrooms, 4 beds, 4.5 bathrooms
2–7 Nov
4.83 out of 5 average rating, 29 reviews
Guest favourite
Villa in Healdsburg
Walk to Downtown Healdsburg | Luxe Vacation Rental
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 73 reviews
Top guest favourite
Home in Healdsburg
Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting
3 bedrooms, 4 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 77 reviews
Top guest favourite
Home in Healdsburg
Vineyard View Retreat • Fire Pit • Wine Perks
2 bedrooms, 3 beds, 2 bathrooms
16–21 Nov
4.96 out of 5 average rating, 98 reviews
Superhost
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
2 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
4.9 out of 5 average rating, 266 reviews