Healdsburg California USA Vacation Rentals by Owner

• • 16 photosWine Country Farmhouse in Vineyard ~ Walk to Healdsburg Plaza - Healdsburg [#1628]
    • 2BR/2BA (Sleeps 6) From $400/nt - $1000/wknd - $2500/wk US Dollars
  • 16 photos4 Bed/4 Bath Remodeled Retreat W/Solar Heated Pool/Spa/Views - Healdsburg [#20282]
    • 4BR+/4BA (Sleeps 10-12) $500-$800/nt - $2000-$4000/wk US Dollars
  • 16 photosCharming Home & Guest Cottage on the River - Healdsburg [#22352]
    • 3BR/2BA (Sleeps 8) $333-$525/nt - $2021-$3255/wk US Dollars
  • 16 photosWine Country Home, Cottages, Pool, and Hot Tub with Huge Lawn - Healdsburg [#26521]
    • 4BR+/2BA (Sleeps 12-14) $450-$550/nt - $2750/wk US Dollars
  • 16 photosFirefly - Sparkling Beachfront Home in Healdsburg, Kayaks, Spa - Healdsburg [#28241]
    • 4BR+/2BA (Sleeps 12) $399-$795/nt US Dollars
  • 16 photosTwo River-Side Wine Country Homes on 7 Acre Twin Towers Ranch - Healdsburg [#32456]
    • 6BR/6BA (Sleeps 16) $800-$1500/wknd - $1800-$3500/wk US Dollars
  • 16 photosOur House Healdsburg Elegance in the Vineyards - Healdsburg [#47463]
    • 6BR+/4BA (Sleeps 12) $4900-$5700/wk US Dollars
  • 16 photosHealdsburg Pension Amongst the Vines - Healdsburg [#65664]
    • 1BR/1BA (Sleeps 2) $200/nt - $1270/wk US Dollars
  • 16 photosFabulous Lake & Sunset Views - Bocce Ball Court - Privacy - Healdsburg [#70467]
    • 4BR/2BA (Sleeps 8) 3 NIGHTS FOR PRICE OF 2 !! US Dollars
  • 16 photosCancellation Leaves June 26-29 Open! Farmhouse with Pool/Spa - Healdsburg [#73975]
    • 5BR+/2.5BA (Sleeps 10-12) $525-$625/nt - $3300-$4100/wk US Dollars
  • 16 photosHarvest House & Cottage: Orchard, Chefs Kitchen, Heated Pool - Healdsburg [#90703]
    • 3BR+/3BA (Sleeps 10) From $595/nt - $2900wk April Free Night US Dollars
  • 16 photosRomantic Luxury Riverside Home Screened Porch, Dock & Canoe! - Healdsburg [#90734]
    • 2BR+/1BA (Sleeps 4) $395/nt up to 4 guests US Dollars
  • 16 photosRiovino - Retro Contemporary in Healdsburg - Healdsburg [#97395]
    • 2BR/1BA (Sleeps 4) From $195/nt US Dollars
  • 16 photosLuxury Tuscan Villa Vineyard Estate - Healdsburg [#136903]
    • 4BR+/3.5BA (Sleeps 8-10) $595-$795/nt US Dollars
  • 16 photosVilla Tranquillo -Mediterranean Resort Style Estate W/Pool/Spa - Healdsburg [#138099]
    • 4BR+/4BA (Sleeps 8) $695-$795/nt US Dollars
  • 16 photosAmazing Turn-of-Century Remodeled Stable Now Vacation Rental - Healdsburg [#153093]
    • 5BR+/4BA (Sleeps 12-17) From $730/nt US Dollars
  • 16 photosNew/Modern/Private "Dry Creek Villa" W/Views, Hot Tub - Healdsburg [#157406]
    • 2BR+/1BA (Sleeps 4-6) $285/nt - $1,800/wk US Dollars
  • 16 photosPrivate Wine Country Retreat with Views, Large Deck & Spa - Healdsburg [#157960]
    • 2BR+/2BA (Sleeps 4-6) $200-$250/nt US Dollars
  • 16 photosWine Country Home with Sweeping Views - Healdsburg [#166299]
    • 4BR+/3BA (Sleeps 10-11) $400-$650/nt US Dollars
  • 16 photos"Villa Moderna" the Ultimate Wine Country View Estate - Healdsburg [#172713]
    • 4BR+/4.5BA (Sleeps 8) From $850nt - $5,100/wk - $17,000/mo US Dollars
  • 16 photosClassic Riverfront Retreat, Romantic Views, Vaulted Greatroom - Healdsburg [#173421]
    • 3BR+/2.5BA (Sleeps 9) $269-$385/nt for 4 guests US Dollars
  • 16 photosVacation Stimulus! 5 BR Estate W/ Spectacular Valley Views - Healdsburg [#174516]
    • 5BR+/2.75BA (Sleeps 10-14) $595-$795/nt US Dollars
  • 16 photosVacation Stimulus! Winelover's 1922 Farmhouse in Vineyard - Healdsburg [#176766]
    • 3BR+/2BA (Sleeps 6-8) $395-$495/nt US Dollars
  • 16 photosHealdsburg Getaway - Wine Country Escape on Russian River - Healdsburg [#177281]
    • 5BR+/3BA (Sleeps 10-12) $115-$595/nt US Dollars
  • 16 photosVacation Stimulus! Kokopelli Alexander Valley Retreat - Healdsburg [#180491]
    • 3BR+/2.5BA (Sleeps 4-10) $395-$595/nt US Dollars
  • 16 photosVacation Stimulus! Luxury Hillside Haven W/ Spa & Plunge Pool - Healdsburg [#187810]
    • 3BR+/2.5BA (Sleeps 6-8) $495-$695/nt US Dollars
  • 16 photosWine Country Cottage & Vineyard Estate~Plaza Less Than 2 Miles - Healdsburg [#191657]
    • 1BR/1BA (Sleeps 2) From $150/nt US Dollars
  • 16 photosWine Country Home & Vineyards ~ 4 Minutes to Healdsburg Plaza - Healdsburg [#191680]
    • 2BR+/2BA (Sleeps 6) From $375/nt - $950/wknd - $2300/wk US Dollars
  • 16 photosVacation Stimulus! Riverhouse in the Redwoods W/ Spa, Beach - Healdsburg [#192827]
    • 3BR+/2BA (Sleeps 6-8) $395-$595/nt U.S. Dollars
  • 16 photosRomantic Fox Barn Villa in the Vineyards - Healdsburg [#194673]
    • 3BR/3.75BA (Sleeps 2-6) $595-$695/nt US Dollars
  • 16 photosRiverwood - Beautiful Riverfront Home, Hot Tub, Sauna, Beach - Healdsburg [#199733]
    • 4BR+/3BA (Sleeps 14) $455-$739/nt 6 guests U S Dollars
  • 16 photos3 BR Arts and Craftsman Bungalow in World Class Vineyard - Healdsburg [#203819]
    • 3BR/2BA (Sleeps 6) $395-$495/nt US Dollars
  • 16 photosBeautiful Healdsburg Retreat- Walk to Square & Russian River - Healdsburg [#207520]
    • 2BR/1BA (Sleeps 2-4) $200-$250/nt US Dollars
  • 16 photosVacation Stimulus! Magical Ranch Style Vineyard Estate Home - Healdsburg [#209247]
    • 3BR+/3BA (Sleeps 6-12) From $595/nt US Dollars
  • 16 photosWine Country Alexander Valley Retreat-4 Hillside Acres, Pool - Healdsburg [#213387]
    • 4BR/3BA (Sleeps 8) From $595/nt US Dollars
  • 16 photosVacation Stimulus! Dry Creek Valley Ranch W/ Pool & Spa - Healdsburg [#215735]
    • 4BR+/4.5BA (Sleeps 8-14) $495-$795/nt US Dollars
  • 16 photosDry Creek Moderna - Luxury Modern Estate, Dry Creek Valley - Healdsburg [#217211]
    • 4BR+/3BA (Sleeps 8-10) $1200/nt - $7200/wk US Dollars
  • 16 photosHealdsburg Modern Cottages - Four Cottages Downtown Healdsburg - Healdsburg [#218085]
    • 4BR+/4BA (Sleeps 8-12) $250-$500/nt/cottage US Dollars
  • 16 photosBlue Heron House - Riverfront Home with Spa, Views & Beach - Healdsburg [#220369]
    • 4BR+/3.5BA (Sleeps 8) $550/nt, $3,000/wk US Dollars
  • 16 photosJuly/Aug/Sept Open Dates 8acre Pvt Estate,Bocce,Pool,Vineyard - Healdsburg [#224029]
    • 3BR+/3BA (Sleeps 6-8) $580/nt - $3480/wk US Dollars
  • 16 photosVictorian Lady Near the Plaza - 30/nt Minimum Stay - Healdsburg [#224195]
    • 2BR+/2BA (Sleeps 4-7) $2500-$3000/mo US Dollars
  • 16 photosMove Over Neverland, Here Comes Riverview! - Healdsburg [#240445]
    • 2BR+/2BA (Sleeps 4) $275/nt US Dollars
  • 16 photos13,000 Acre Vineyard & Ranch: Mountains, Valleys, and Rivers - Healdsburg [#241448]
    • 8BR+/8BA (Sleeps 2-33) $1039-$1299/nt - $4590/wk US Dollars
  • 16 photosVacation Stimulus!Beautiful Santarini Vineyard Home Near Plaza - Healdsburg [#247204]
    • 3BR/2BA (Sleeps 8) $395-$595/nt US Dollars
      New!
  • 14 photosUpscale Sonoma Wine Country Home & Meeting Escape - Healdsburg [#2529]
    • 4BR+/3BA (Sleeps 8-12) $600/nt - $1400/wknd - $3000/wk US Dollars
  • 14 photosRussian River - Healdsburg River Cottage - Healdsburg [#120376]
    • 2BR/2BA (Sleeps 3-4) $189/nt 2 nt min - $1050/wk US $ Monthly rate avai
  • 14 photosMidsummer Night's Dream Cottage - Healdsburg [#137960]
    • 2BR+/2BA (Sleeps 2-6) From $175/nt US Dollars
  • 14 photosLuxury New Home with Panoramic View, Pool & Spa - Healdsburg [#218289]
    • 2BR+/2BA (Sleeps 4-5) $475/nt - $3000/wk US Dollars
  • 13 photosModern, Barn Style Home, Healdsburg/in Metropolitan Home Mag! - Healdsburg [#53851]
    • 3BR+/3.5BA (Sleeps 6-8) $800-$950/nt US Dollars
  • 13 photos"Le Tournesol" Spacious, Wine Country Home Near Healdsburg - Healdsburg [#172486]
    • 3BR+/2BA (Sleeps 6-8) $450-$500/nt - $2850/wk US Dollars
  • 12 photosBuena Vista River House -Vintage Home,Outstanding River Views - Healdsburg [#14038]
    • 5BR+/1.5BA (Sleeps 8-10) $750-$1000/wknd - $1500-$2000/wk US Dollars
  • 12 photosMoss Hill Lodge - Modern Farmhouse on Stunning Vineyard - Healdsburg [#31027]
    • 4BR+/3.5BA (Sleeps 4-10) From $595/nt - $3275/wk US Dollars
  • 12 photosNo Name Resort - Vacation Home with Pool and Spa - Healdsburg [#31865]
    • 4BR+/3.75BA (Sleeps 8-10) From $325/nt - $3975/wk US Dollars
  • 12 photosFour Sisters Farmhouse - Gorgeous Wine Country Farmhouse - Healdsburg [#95535]
    • 4BR+/3BA (Sleeps 12) $650/nt - $1600/wknd - $4,100/wk US Dollars
  • 12 photosOur Guest's Comments Say it All! Gorgeous Home, Best Value - Healdsburg [#166003]
    • 3BR+/2BA (Sleeps 8) $299-399/nt - $1700-$2300/wk US Dollars
  • 12 photosBright, Sunny and Spacious! - Healdsburg [#167466]
    • 1BR+/1BA (Sleeps 4) $175-$200/nt - $1000-$1200/wk US Dollars
  • 12 photosSecluded Cottage in the Oaks - Healdsburg [#198932]
    • 1BR+/1BA (Sleeps 2-4) $150-$200/nt US Dollars
  • 12 photosGorgeous Healdsburg Wine Country View Estate - Healdsburg [#224985]
    • 4BR/3.5BA (Sleeps 8) $700-$1000/nt - $4500-$6000/wk US Dollars
  • 10 photosSpectacular Hillside House, Views, Beach Access, Hot Tub - Healdsburg [#90050]
    • 3BR+/2BA (Sleeps 8) $195-$375/nt - $1546-$1875/wk US Dollars
  • 10 photosAlexander Valley Vineyard Vacation Studio - Healdsburg [#241800]
    • 1BR/1BA (Sleeps 1-2) $295/nt US Dollars
  • 9 photosAlexander Valley Lodge - Pool, Jacuzzi, Waterfall, & Tiki Bar - Healdsburg [#56107]
    • 6BR+/5BA (Sleeps 14-18) From $495/nt - $5200/wk US Dollars
  • 9 photosHealdsburg Wine Country Luxury Estate - Healdsburg [#134752]
    • 5BR+/4.5BA (Sleeps 10-14) $1250/nt US Dollars
  • 9 photosWine Country Retreat - Healdsburg [#160614]
    • 1BR+/1BA (Sleeps 2-4) From $125/nt - $800/wk US Dollars
  • 9 photosReduced Price - Emma's Cottage - Perfect for Wine Lovers! - Healdsburg [#203771]
    • 3BR/2BA (Sleeps 6-8) $295-$395/nt US Dollars
  • 9 photosCountry Garden Cottage Overlooking Russian River Valley - Healdsburg [#228670]
    • 1BR+/1BA (Sleeps 2-4) $135-$150/nt - $700/wk US Dollars
  • 8 photosWine Country Vacation Home in Healdsburg on Private Vineyard - Healdsburg [#66807]
    • 2BR+/1BA (Sleeps 4-6) $379/nt 2 nt min - $1701/wk - $3500/mo US Dollars
  • 8 photosWine Country Getaway in Historic Healdsburg--Walk to the Plaza - Healdsburg [#138622]
    • 2BR/1BA (Sleeps 2-4) $375-$450/nt - $4500/mo US Dollars
  • 8 photosDry Creek Valley Home and Vineyard - Healdsburg [#199349]
    • 3BR+/3.5BA (Sleeps 8) $499/nt US Dollars
  • 8 photosHealdsburg Country Cabin in Beautiful Dry Creek Valley - Healdsburg [#201671]
    • 2BR+/1BA (Sleeps 4) $179-$199/nt US Dollars
  • 7 photosGorgeous Wine Country Retreat - Healdsburg [#13152]
    • 2BR+/2BA (Sleeps 6) $190-$415/nt US Dollars
  • 7 photosThe Inn at Le Vin Estate Winery & Vineyards - Healdsburg [#76664]
    • 1BR+/1.5BA (Sleeps 2-4) From $175/nt - $1000/wk US Dollars
  • 7 photosPrivate 8 Acre Wine Country Getaway in Dry Creek Valley - Healdsburg [#136814]
    • 3BR+/3BA (Sleeps 10-12) $750-950/nt - $4350-$5000/wk US Dollars
  • 7 photosCheck Out This Pool! Healdsburg/Forestville Location - Healdsburg [#195392]
    • 3BR/2BA (Sleeps 6) $500-$600/nt - $3000-$3600/wk US Dollars
  • 7 photosA Jewel in the Outer Dry Creek Valley Surrounded by Vineyards - Healdsburg [#208232]
    • 4BR+/4BA (Sleeps 8-10) $776/nt US Dollars
  • 7 photosBeautiful Gardens and Vineyard Views Surround Stillerus - Healdsburg [#209020]
    • 3BR+/2BA (Sleeps 6-10) $726/nt US Dollars
  • 7 photosSit on the Deck and Watch the Sunset from Interlude - Healdsburg [#209031]
    • 3BR+/2BA (Sleeps 6-7) $625/nt US Dollars
  • 7 photosSpacious Ranch Home with Vineyard Views- Le Petit Olivet - Healdsburg [#209038]
    • 3BR+/3.5BA (Sleeps 6-8) $469/nt US Dollars
  • 7 photosVilla Ariadna a Private Country Home in the Dry Creek Valley - Healdsburg [#209046]
    • 4BR/4BA (Sleeps 8) $675/nt US Dollars
  • 7 photosCharming Restored Farmhouse in Geyserville - Beaux Reves - Healdsburg [#209054]
    • 4BR/2BA (Sleeps 8) $417/nt US Dollars
  • 7 photosJimtown House- Near the Jimtown Store in Alexander Valley - Healdsburg [#209064]
    • 3BR/2BA (Sleeps 6) $417/nt US Dollars
  • 7 photosValley Oak Manor- Country Home with Lots of Charm - Healdsburg [#209070]
    • 4BR+/2BA (Sleeps 8-10) $520/nt US Dollars
  • 6 photosVineyard Haven - Your Wine Country Getaway! - Healdsburg [#70218]
    • 3BR+/2BA (Sleeps 6-7) Low Season $350/nt - High Season $400/nt US Dollars
  • 6 photosAlexander Valley Elegant Log Cabin Amid Vineyards and Wildlife - Healdsburg [#227710]
    • 2BR/1BA (Sleeps 4) $195-$275/nt, $1100-$1500/wk. US Dollars
  • 5 photosPrivate Studio Apartment with Stunning Vineyard Views - Healdsburg [#68270]
    • 1BR/1BA (Sleeps 2) $175-$225/nt - $450/wknd US Dollars
  • 5 photosHealdsburg Cottage in Historic Downtown - Walk to the Plaza - Healdsburg [#91570]
    • 1BR+/1BA (Sleeps 2-4) From $125/nt US Dollars
  • 5 photos1BR Manor Guesthouse Off Plaza with Pool and Jacuzzi - Healdsburg [#104117]
    • 1BR/1BA (Sleeps 1-2) From $245/nt US Dollars
  • 5 photosHealdsburg Vacation Home with Redwoods & Creek - Healdsburg [#119607]
    • 3BR+/2.5BA (Sleeps 7-10) $476-$555/nt US Dollars
  • 5 photosHealdsburg Chalk Hill Valley 3 BR on 3 Acres Yet Close to Town - Healdsburg [#127675]
    • 4BR+/3BA (Sleeps 4-8) $139-$475/nt US Dollars
  • 5 photosVictorian Farmhouse - Healdsburg [#141763]
    • 2BR/2BA (Sleeps 4-5) $200-$250/nt US Dollars
  • 5 photosLovely Home in Quiet Healdsburg Neighborhood - Healdsburg [#144608]
    • 3BR/2BA (Sleeps 3-6) $2800/mo US Dollars
  • 5 photosCharming 2BR/1BA Bungalow. Hot Tub. Swimming Pool. Backyard. - Healdsburg [#147990]
    • 2BR/1BA (Sleeps 4-6) From $175/nt - $1475/wk US Dollars
  • 5 photosPrivate Beach, Charming Northwoods Cottage, Spa, Kayaks, Dock - Healdsburg [#170592]
    • 3BR+/2BA (Sleeps 8) $239-$489/nt US Dollars
  • 5 photosCountry Cottage with Hobby Vineyard - Healdsburg [#174134]
    • 1BR/1BA (Sleeps 2) From $135/nt US Dollars
  • 5 photosRiver-Nook Stunning, Private Riverfront Healdsburg - Healdsburg [#191221]
    • 2BR/1BA (Sleeps 4) $195-$290/nt - $1150-$1590/wk US Dollars
  • 5 photosDowntown Healdsburg ~ 2 Blocks from Historic Downtown Plaza - Healdsburg [#196846]
    • 2BR+/1BA (Sleeps 6-8) $200/nt US Dollars
  • 5 photosRussian River Cabin in Healdsburg - Healdsburg [#205776]
    • 2BR/1BA (Sleeps 4) From $145/nt - $600/wk US Dollars
  • 5 photosMinutes from Downtown Healdsburg - Healdsburg [#208280]
    • 4BR+/2BA (Sleeps 8-10) From $200/nt US Dollars
  • 5 photosAlexander Valley Cottage in the Vineyards of Healdsburg - Healdsburg [#210370]
    • 3BR/3BA (Sleeps 6) From $390/nt - $1800/wk US Dollars
  • 5 photosVineyard Ranch House in Dry Creek Valley, Sonoma - Healdsburg [#211703]
    • 3BR/2BA (Sleeps 6) $300-$350/nt - $1800/wk US Dollars
  • 5 photosCharming Wine Country Cottage in Historic Healdsburg - Healdsburg [#231648]
    • 2BR/2BA (Sleeps 2-4) $325-$550/nt US Dollars
  • 5 photosCome Experience Life Among the Vines on a Working Winery - Healdsburg [#235142]
    • 1BR/1BA (Sleeps 2) $95/nt-$195/nt US Dollars
  • 5 photosStunning, Serene Views - Healdsburg [#236817]
    • 3BR+/2.75BA (Sleeps 6) $500/nt - $1250/wknd - $2900/wk US Dollars
  • 5 photosCharming Home Overlooking the Russian River - Healdsburg [#238306]
    • 2BR+/2BA (Sleeps 5-7) $2300-$2500/wk - $3000/mo US Dollars
  • 5 photosViews Chalk Hill Valley in This Bright Large Country Studio - Healdsburg [#239646]
    • 1BR+/1BA (Sleeps 2-3) From $125/nt US Dollars
  • 4 photos2 Bedroom Cottage in Healdsburg's Dry Creek Valley! - Healdsburg [#222265]
    • 2BR/1BA (Sleeps 4) $275/nt - $1600/wk US Dollars
  • 3 photosRiver Relaxation Near Healdsburg - Healdsburg [#59572]
    • 3BR/2BA (Sleeps 3-6) $300/nt - $400/wknd - $1000/wk off seas US Dollars
  • 3 photosAffordable Wine Country Vacation Rentals in Healdsburg Area - Healdsburg [#160216]
    • 2BR+/1BA (Sleeps 2-7) $350-$425/nt US Dollars
  • 3 photosHealdsburg - Chalk Hill Wine Country Cottage - Healdsburg [#162988]
    • 1BR+/1BA (Sleeps 2-4) $140-$190/nt US Dollars
  • 0 photosCabin in Alexander Valley - Healdsburg [#79912]
    • 3BR+/2BA (Sleeps 6-8) From $450/nt - $2300/wk US Dollars

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