Skip to content
21 stays

Stays in Healdsburg

Enter dates and number of guests to see the total price per night.
Review COVID-19 travel restrictions before you book.
Learn more
SUPERHOST
Entire villa in Healdsburg
Chix Villa- on our family century+ Zin vineyard
2 guests1 bedroom1 bed1 bathroom
WifiHeating
LUXE
Entire villa in Santa Rosa
The Sonoma Ranch
6 guests4 bedrooms4 beds4.5 bathrooms
Lap poolSonos sound systemGas fireplace
SUPERHOST
Entire villa in Healdsburg
Trinite Estate
10 guests5 bedrooms7 beds4.5 bathrooms
Hot tubWifiKitchenHeating
SUPERHOST
Entire villa in Healdsburg
Casa de Campo 4/3 house with pool
10 guests4 bedrooms5 beds3 bathrooms
WifiKitchenHeating
LUXE
Entire villa in Healdsburg
Decanter Healdsburg
6 guests3 bedrooms5 beds4 bathrooms
PoolSun loungersHot tub
Entire villa in Windsor
Luxury Modern Farmhouse with Pool, Spa and Peloton
8 guests4 bedrooms5 beds2 bathrooms
Hot tubWifiKitchenHeating
Entire villa in Geyserville
Modern Elegance with Serene Wine Country Views
10 guests4 bedrooms6 beds5 bathrooms
Hot tubWifiKitchenHeating
LUXE
Entire villa in Healdsburg
Healdsburg Villa and Farm · Tuscan Revival villa atop the vineyards
8 guests4 bedrooms4 beds3 bathrooms
Fire pitPoolChef's kitchen
LUXE
Entire villa in Healdsburg
Alexander Valley Estate · Vintage ranch-style house in Alexander Valley
11 guests5 bedrooms6 beds4.5 bathrooms
PoolTerraceSonos sound systemBBQ grill
Entire villa in Healdsburg
Healdsburg's Finest Retreat
8 guests3 bedrooms5 beds2 bathrooms
Hot tubWifiKitchenHeating
SUPERHOST
Entire villa in Healdsburg
Secluded Vineyard Estate Healdsburg
10 guests4 bedrooms5 beds4 bathrooms
Hot tubWifiKitchenHeating
LUXE
Entire villa in Healdsburg
New Tree Ranch
8 guests4 bedrooms5 beds4 bathrooms
Fire pitHousekeepingPool
SUPERHOST
Entire villa in Healdsburg
Creek Front Vineyard, West Dry Creek Healdsburg CA
12 guests6 bedrooms6 beds6.5 bathrooms
Hot tubWifiKitchenHeating
Entire villa in Healdsburg
Whispering Oaks Estate
8 guests4 bedrooms4 beds5 bathrooms
WifiKitchenHeating
SUPERHOST
Entire villa in Geyserville
Alexander Valley Lodge Pool/Hot Tub
12 guests5 bedrooms15 beds5 bathrooms
Hot tubWifiKitchenHeating
SUPERHOST
Private room in Geyserville
Alexander Valley Lodge Valley View
4 guests1 bedroom2 beds1 bathroom
Hot tubWifiHeating
Entire villa in Healdsburg
Entire Wine Country Villa
10 guests5 bedrooms8 beds5 bathrooms
Hot tubWifiKitchenHeating
LUXE
Entire villa in Windsor
CatDen Vineyards
8 guests3 bedrooms4 beds3 bathrooms
Fire pitGas fireplaceSun loungersSound system
Entire villa in Healdsburg
Healdsburg Residence in Dry Creek Valley
8 guests4 bedrooms5 beds6 bathrooms
Hot tubWifiKitchenHeating
LUXE
Entire villa in Healdsburg
Lytton Springs
6 guests4 bedrooms5 beds3.5 bathrooms
Fire pitPoolTerraceBar with built-in sink
120 of 21 villas
Enter dates to see full pricing. Additional fees apply. Taxes may be added.