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Search results; Over 1,000 homes in Healdsburg

Top guest favourite
Home in Healdsburg
Three-Building Healdsburg Homestead with Wine Barn
4 bedrooms, 4 beds, 1.5 private bathrooms
10–15 Jul
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4.86 out of 5 average rating, 155 reviews
Featured hotel
Hotel in Healdsburg
Healdsburg king
1 bedroom, 1 king bed, 1 bathroom
15–20 Nov
Guest favourite
Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
1 bedroom, 1 queen bed, 1 bathroom
14–19 Jul
4.93 out of 5 average rating, 472 reviews
Top guest favourite
Guest house in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 312 reviews
Superhost
Place to stay in Healdsburg
The Estate Overlook Room · Bella Villa Messina
1 bedroom, 1 queen bed, 2 bathrooms
5–10 Jul
Guest favourite
Villa in Healdsburg
Hilltop Villa with Sweeping Views & Trail Access
2 bedrooms, 2 king beds, 2 bathrooms
5–10 Jul
4.94 out of 5 average rating, 194 reviews
Top guest favourite
Cottage in Healdsburg
Charming Cottage in Sonoma Wine Country
1 bedroom, 2 beds, 1 bathroom
12–17 Jul
4.84 out of 5 average rating, 89 reviews
Top guest favourite
Home in Healdsburg
10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
2 bedrooms, 3 queen beds, 1.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 246 reviews
Top guest favourite
Home in Healdsburg
Wake Up in Your Own Private Vineyard - Healdsburg
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.98 out of 5 average rating, 179 reviews
Guest favourite
Home in Healdsburg
Rivers Breeze - Wine Tastings Included
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.88 out of 5 average rating, 50 reviews
Guest favourite
Guest house in Healdsburg
Healdsburg Contemporary Cottage With Lush Backyard
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
4.97 out of 5 average rating, 248 reviews
Luxe
Home in Healdsburg
Dry Creek Modern
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Jul
5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Healdsburg
Vintage Home in Healdsburg Wine Country
3 bedrooms, 5 beds, 3 bathrooms
11–16 Jul
4.87 out of 5 average rating, 53 reviews
Guest favourite
Home in Healdsburg
Wine Country Cottage in Healdsburg
1 bedroom, 1 queen bed, 1 bathroom
5–10 Aug
4.88 out of 5 average rating, 418 reviews
Top guest favourite
Hotel room in Healdsburg
Two Thirty-Five Luxury Suites: Plaza Suite
3 bedrooms, 3 king beds, 3.5 bathrooms
5–10 Jul
4.99 out of 5 average rating, 89 reviews
Top guest favourite
Home in Healdsburg
Villa with Pool, Hot Tub and Tastings Included
2 bedrooms, 3 king beds, 2.5 bathrooms
5–10 Jul
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Home in Healdsburg
The Healdsburg Haven
4 bedrooms, 5 beds, 3 bathrooms
11–16 Jul
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Home in Healdsburg
Luxury Retreat w/ Pool, Hot Tub & Sauna
3 bedrooms, 4 beds, 3 bathrooms
11–16 Jul
4.99 out of 5 average rating, 122 reviews
Top guest favourite
Home in Healdsburg
WC Oasis with Hot Tub - Wine Tastings Included
4 bedrooms, 5 beds, 4 bathrooms
9–14 Aug
4.95 out of 5 average rating, 60 reviews