Vacation Rentals in Healdsburg, California

50 Properties Available

Modern, recently built home with stunning pool & beautiful views; 15 min to town Private vacation home
Modern, recently built home with stunning pool & beautiful views; 15 min to town
$2184 / night
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Healdsburg Luxury Villa Estate | Private Boutique Stay Near Plaza & Wineries Villa
Healdsburg Luxury Villa Estate | Private Boutique Stay Near Plaza & Wineries
$1998 / night
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Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets Private vacation home
Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets
$1828 / night
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Amazing Resort-like Estate Near Healdsburg, CA Private vacation home
Amazing Resort-like Estate Near Healdsburg, CA
$1743 / night
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Close to Plaza\/15 Acre Estate\/Swimming Pool and Bocce Ball Private vacation home
Close to Plaza\/15 Acre Estate\/Swimming Pool and Bocce Ball
$1440 / night
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Large Outdoor Kitchen, Pool, Hot Tub, Firepit...8 Mins From Healdsburg Plaza Private vacation home
Large Outdoor Kitchen, Pool, Hot Tub, Firepit...8 Mins From Healdsburg Plaza
$1398 / night
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Dry Creek Ranch ~ Pool, HotTub, & Game Barn! Private vacation home
Dry Creek Ranch ~ Pool, HotTub, & Game Barn!
$1338 / night
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Healdsburg Plaza Gem-Hot Tub and Tastings Included Private vacation home
Healdsburg Plaza Gem-Hot Tub and Tastings Included
$1328 / night
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River View Lodge - Hot Tub and Tastings Included Private vacation home
River View Lodge - Hot Tub and Tastings Included
$1318 / night
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Stunning Retreat Overlooking Vineyards w\/ Pool, Hot Tub & Guest Suite Private vacation home
Stunning Retreat Overlooking Vineyards w\/ Pool, Hot Tub & Guest Suite
$1294 / night
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Rendezvous Under the Oaks-Pool & hot Spa Private vacation home
Rendezvous Under the Oaks-Pool & hot Spa
$1271 / night
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Hidden Oasis ~ a Private Luxury Home in Healdsburg Private vacation home
Hidden Oasis ~ a Private Luxury Home in Healdsburg
$1209 / night
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Healdsburg Luxe Reserve for 8, pool, spa, firepit Private vacation home
Healdsburg Luxe Reserve for 8, pool, spa, firepit
$1174 / night
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Wake Up in Your Own Private Vineyard - Healdsburg Private vacation home
Wake Up in Your Own Private Vineyard - Healdsburg
$1065 / night
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Ultimate staycation on the vineyard, Pool, hot tub with 5 ensuite bed\/ 6 bath Private vacation home
Ultimate staycation on the vineyard, Pool, hot tub with 5 ensuite bed\/ 6 bath
$999 / night
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Family-Friendly Dry Creek Valley Retreat w\/Amazing Views <15 Minutes To Square Private vacation home
Family-Friendly Dry Creek Valley Retreat w\/Amazing Views <15 Minutes To Square
$994 / night
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Serenity with Hot Tub and Wine Tastings Included Private vacation home
Serenity with Hot Tub and Wine Tastings Included
$930 / night
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Cypress House & Studio, Walk to Healdsburg Plaza by RedAwning Private vacation home
Cypress House & Studio, Walk to Healdsburg Plaza by RedAwning
$905 / night
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Casa Chiquita-The Coziest in Town, 3 Bed, 3 full Bath, Spa & Pool Private vacation home
Casa Chiquita-The Coziest in Town, 3 Bed, 3 full Bath, Spa & Pool
$875 / night
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WINE COUNTRY CHIC AND ELEGANCE! BEST LOCATION! TURN KEY! Private vacation home
WINE COUNTRY CHIC AND ELEGANCE! BEST LOCATION! TURN KEY!
$850 / night
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6Beds 3Bath - Pool, Hot Tub, Pets Welcome, Fire Pit- 1mi to Downtown Private vacation home
6Beds 3Bath - Pool, Hot Tub, Pets Welcome, Fire Pit- 1mi to Downtown
$808 / night
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Modern Wine Country Cottage in Historic Healdsburg, Premiere Location Private vacation home
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
$722 / night
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Haven at Healdsburg, by Vinifera Homes Private vacation home
Haven at Healdsburg, by Vinifera Homes
$709 / night
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4 bedroom home at the gateway to Alexander Valley. Private vacation home
4 bedroom home at the gateway to Alexander Valley.
$671 / night
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Wine country retreat Private vacation home
Wine country retreat
$616 / night
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Contemporary Designer Cottage, Garden View, 3 Blocks From From The Plaza Cottage
Contemporary Designer Cottage, Garden View, 3 Blocks From From The Plaza
$575 / night
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Redwood Riverfront - Hot Tub and Tastings Included Private vacation home
Redwood Riverfront - Hot Tub and Tastings Included
$538 / night
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Private Acre with BBQ, Patio, 5min to Healdsburg Plaza Private vacation home
Private Acre with BBQ, Patio, 5min to Healdsburg Plaza
$507 / night
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Vineyard View Retreat • Fire Pit • Wine Tasting Perks Private vacation home
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
$400 / night
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Russian Riverside Cottage in Healdsburg Cottage
Russian Riverside Cottage in Healdsburg
$399 / night
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Beautiful Mountain Top Retreat (MTR) less than 10 mins from downtown Healdsburg! Private vacation home
Beautiful Mountain Top Retreat (MTR) less than 10 mins from downtown Healdsburg!
$358 / night
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luxuriously appointed new large guest suite in a landmark Victorian Private vacation home
luxuriously appointed new large guest suite in a landmark Victorian
$348 / night
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Choice Getaway w\/ Private Hot Tub - Near Wineries, Dining, Outdoor Activities Private vacation home
Choice Getaway w\/ Private Hot Tub - Near Wineries, Dining, Outdoor Activities
$342 / night
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Beautiful Studio Getaway in the Heart of Wine Country Guest house
Beautiful Studio Getaway in the Heart of Wine Country
$324 / night
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Luminous and cozy studio one block from Healdsburg's idyllic plaza! Apartment
Luminous and cozy studio one block from Healdsburg's idyllic plaza!
$289 / night
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Chalk Hill Cottage Close to Wineries Cottage
Chalk Hill Cottage Close to Wineries
$281 / night
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Modern Townhome - Walking Distance to Healdsburg Plaza Private vacation home
Modern Townhome - Walking Distance to Healdsburg Plaza
$267 / night
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Healdsburg - Stunning wine country retreat - work, play and enjoy! Private vacation home
Healdsburg - Stunning wine country retreat - work, play and enjoy!
$261 / night
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Luxury new studio in downtown Healdsburg with WiFi, AC Apartment
Luxury new studio in downtown Healdsburg with WiFi, AC
$255 / night
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Chic wine country cottage and garden Cottage
Chic wine country cottage and garden
$246 / night
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Contemporary style meets country charm for ideal Wine Country living. Private vacation home
Contemporary style meets country charm for ideal Wine Country living.
$243 / night
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Downtown Healdsburg home with fenced yard, grill, WiFi, central AC, and W\/D Private vacation home
Downtown Healdsburg home with fenced yard, grill, WiFi, central AC, and W\/D
$227 / night
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Wine Country Vacation Home w\/ Fireplace! Private vacation home
Wine Country Vacation Home w\/ Fireplace!
$195 / night
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Best Western Dry Creek Inn Hotel
Best Western Dry Creek Inn
$159 / night
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Hotel Vinea, a Travelodge by Wyndham Motel
Hotel Vinea, a Travelodge by Wyndham
$127 / night
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The Bird Nest - Luxury Studio Residence in Historic Healdsburg Apartment
The Bird Nest - Luxury Studio Residence in Historic Healdsburg
$126 / night
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Updated Healdsburg River Cottage: Minutes from Plaza, Tasting Rooms & Vineyards Cottage
Updated Healdsburg River Cottage: Minutes from Plaza, Tasting Rooms & Vineyards
$119 / night
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Cypress House & Studio, Walk To Healdsburg Plaza 3 Bedroom Home by Redawning Private vacation home
Cypress House & Studio, Walk To Healdsburg Plaza 3 Bedroom Home by Redawning
$0 / night
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Downtown Healdsburg Luxury Glass Pavilion Private vacation home
Downtown Healdsburg Luxury Glass Pavilion
$0 / night
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Hidden Gem! 3br Private Luxury Oasis In Healdsburg 3 Bedroom Home by RedAwning Private vacation home
Hidden Gem! 3br Private Luxury Oasis In Healdsburg 3 Bedroom Home by RedAwning
$0 / night
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