Home Vacation Rentals By Owner In Healdsburg, CA

Showing 60 Of 177 Vacation Rentals
Slider Thumb

$159.68

/ Nightly
Private Vacation Home

Mid-Century Healdsburg Bungalow meets Modern Contemporary 2BR/2BA, walk to town

Healdsburg, California, United States

Mid-Century Wine Retreat - 31 Day Minimumbr br“Four blocks to the Plaza, Your Retreat to Wine Country Elegance.”br brWelcome to your private Healdsburg retreat—an elegantly newly remodeled mid-century single-story home just a short stroll from the renowned Plaza.br brThis spacious and accommodating residence offers 2 bedrooms and bonus room with sleeper sofa. Featuring a separate-entry guest suite, perfect for hosting family or friends with privacy and comfort and access to outdoor patio. Inside, you’ll enjoy a bright family room with an oversized TV for movie nights, plus a lovely library that invites quiet reading or can double as an extra sleeping area. Every detail has been refreshed with all-new furnishings, premium bedding, and updated hardware throughout.br brStep outside to the expansive garden grounds, featuring a newly landscaped front yard, a tranquil grove of fruit and shade trees, and a generous backyard oasis designed for relaxation. The brick patio, shaded by a stunning Japanese maple, sets the stage for al fresco dining, barbecues, or simply enjoying a glass of wine in the fresh Sonoma air.br brWhether you’re seeking a restful month-long stay, a wine country escape, or an extended retreat close to the best of downtown Healdsburg, this home offers a rare combination of style, comfort, and location.brDRE 01156682
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb

$1085.25

/ Nightly
Private Vacation Home

Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza

Healdsburg, California, United States

Every season is magical at the Dry Creek Farm Stay! Year-round in-ground Spa and seasonally heated Pool with vine-covered poolside pergola for family meals in the fresh air. Many sustainability features including 100% self-generated 15kw solar power array with Tesla Powerwalls so that power shutdowns won’t spoil your vacation. Nest thermostats, warm floors and radiators heated with solar hot water system for natural warmth. All bedrooms feature energy efficient multizone AC for those famously warm Summer days in Dry Creek Summer months.brbr———————————————brSweeping views of Geyser Peak and Dry Creek Valley may be highlighted by morning fog any time of year, and the light playing across the vineyard contours changes minute to minute. The warm summer nights by the pool...fall colors and natural beauty of the Dry Creek Valley exceed expectations, and we would love to have you visit! Perfect for nature lovers and wine tasters alike, great starting point for many beautiful bicycle rides/tours in the Healdsburg area. House is situated on a 20 acre dog-friendly fenced property with five acres of Syrah and Valpolicella blend vineyards, a seasonal creek and a wonderful mixture of benchland and upland flora and fauna. Quiet nights with stars abound, listen to the owl duets, and the ongoing symphony of wild nature!brbrCome and immerse yourself in this private, retreat to experience the Sonoma County way of life. Stone terrace surrounds the pool and in-ground hot tub and also includes a poolside pergola, unique changing cabana /enclosed outdoor shower. brbrGourmet kitchen with huge Garland range (two ovens, salamander) Subzero fridge and island for communal food prep. Large handcrafted dining room table seats ten to twelve. Handmade Windsor chairs by American woodworker/artisans are beautiful and comfortable. brbrCentral Air Conditioning in the upstairs bedrooms. makes for comfortable sleep and indoor time for any days that get extra hot. Energy efficient home by Siegel and Strain architects of Emeryville, California includes hydronically heated stone and tile floors in the winter and other green amenities including Solar hot water systems and a photovoltaic array provide the electricity for the farm, and now battery system provides continuous power even during energy shutdowns. Electric vehicle charging station provided on the premises.brbrThe Dry Creek Farm Stay holds a valid permit with Sonoma County as a vacation rental (Transient Occupancy Tax Certificate # 1014N)brbrQuiet Hours in Sonoma County are 10pm to 7ambrbrMaximum number of guests allowed by Sonoma County in this residence is 8, but homeowner may limit guest count further due to limited resources (esp. water). Maximum number of guest vehicles allowed on this property per Sonoma County ordinance is 3 vehicles. Owner may be able to assist guests with management of additional cars as needed since parking is plentiful inside this 20 acre property (but car traffic coming and going on the road must be limited). Please inquire via email for monthly rates.
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(1)

$578.67

/ Nightly
Private Vacation Home

Stunning Sonoma 3BR, 3BA house w/view, lap pool, hot tub, Tesla chgr, Healdsburg

Healdsburg, California, United States

Welcome to our 20 acre vineyard with stunning views in Healdsburg on West Dry Creek Rd. Perfect for indoor/outdoor living with floor to ceiling glass sliding doors to enjoy the view. Exercise in the 60 ft lap pool, sit and sip wine by the pool, enjoy the large hot tub, take a beautiful walk or a world-famous bike ride down West Dry Creek Road. Enjoy the beautiful gas fire pit next to the pool for late night conversations. There is even a large pond on the property.brbrWith 3 bedrooms including 2 king BR and 1 queen BR all with ensuite full bathrooms, this sustainable property offers all the comforts you need. The 3 full bathrooms come equipped with a shower, bathtub, and even a bidet. Organic Naturepedic mattresses, Coyuchi Organic linens. Fully equipped kitchen. A brilliant choice for guests looking for a relaxing or fun family getaway as everyone can gather in the great room and around the indoor and outdoor fireplaces. brbrVisit the dozens of boutique wineries nearby and the Healdsburg square packed with gourmet restaurants is just a 12 min drive. Originally a gathering for an Organic Beauty Company started by the owner, we've hosted celebrities, influencers, friends and anyone wanting to have fun and relax. brbrThis is a terrific 1-2+ month rental for an extended vacation. A great place to call home-base, we hope you enjoy your stay.
Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(4)

$991.95

/ Nightly
Private Vacation Home

Eastside Eden - Pool, Hot Tub and Tastings Included

Healdsburg, California, United States

Summary:brbrLocated just 10 min. from the Plaza | Elevate your by booking our Healdsburg farmhouse with vineyard views, pool/hot tub, gourmet kitchen and complimentary tastings!brbrbrbrThe Space:brbrExperience the beauty of Sonoma County with a stay at this charming farm house. Boasting 3 bedrooms and 3.5 bathrooms, this historic property offers a glimpse into the rich heritage of wine country.brbrbrbrAs you step inside, you'll be greeted by a spacious gourmet kitchen that seamlessly flows into the dining area, living room, and wrap-around deck. This open layout ensures that everyone can gather together and enjoy the exceptional views that surround the property.brbrbrbrThe farm house is nestled amidst picturesque vineyards that produce award-winning wines, offering a truly immersive experience in the heart of wine country. You'll have the opportunity to witness the working vineyard in action as it is actively farmed, adding to the authenticity of your stay.brbrbrbrA highlight of this property is the newly installed in-ground pool, complete with a hot tub for ultimate relaxation. The garden area provides a serene space to unwind, while the Weber gas grill allows you to indulge in some outdoor cooking. Additionally, the pool bathroom with a shower and wine cellar add to the convenience and luxury of this one-of-a-kind wine country living experience.brbrbrbrWake up each morning to breathtaking views and savor a cup of coffee or a glass of wine on the deck as you soak in the stunning surroundings. This farm house offers the perfect blend of history, natural beauty, and modern amenities, ensuring an unforgettable stay in Sonoma County.brbrbrbrAlong with the property’s charm and prime location, we provide personalized hospitality. Expect attentive support, clear communication, and a warm welcome that makes your stay effortless.brbrbrbrLocal Winery Partnerships | Elevate Your Stay with Complimentary TastingsbrbrbrbrAs our guest, you’re invited to elevate your Wine Country stay with complimentary tastings at several small, locally owned wineries (Guest of record must be present for all tastings)brbrbrbr• Merriam Vineyards – a family-owned estate crafting elegant, Old World–inspired Bordeaux-style wines; a $35 value per guest, complimentary for up to six guests.brbr• Orsi Family Vineyards – a locally loved winery specializing in expressive, small-lot Italian varietals like Sangiovese and Schioppettino; a $35 value per guest, complimentary for up to six guests.brbr• Stonemason Cellars – Small lot wines all sourced locally from Sonoma County grapes. Enjoy their Nibbles & Wine tasting experience ($35 value per person)brbrbrbrA unforgettable way to toast your Wine Country getaway — cheers to delicious moments ahead!brbrbrbrAbout the space:brbr• Main level: Living Room, Kitchen, Dining area, breakfast nook, half bathroom, twin daybed in kitchen area.brbr• 2nd level: 3 bedrooms (2 King beds, 1 Queen), 2 full bathroomsbrbr• Pool House: Half bathroom with separate shower. Pool heating available, rates vary by season.brbr• Pool Depth: 3'6 - 6'6. Pool Dimensions: 16'x36'.brbr• Drip coffee maker available for guest use (coffee not supplied). Kitchen is equipped with a SodaStream, two blenders, kitchen aid mixer, food processor, popcorn maker, hand blender, French Press and Creuset pot set. brbr• Only 10 minutes from the Healdsburg Plaza.brbr• Pets negotiable.brbrbrbrClimate Control: The downstairs living areas feature central heating and air conditioning, while each upstairs bedroom is equipped with its own individual heating and AC unit for personalized comfort.brbrShould the power go out the house is equipped with a backup generator that will automatically turn on during an outage.brbrbrbrPermit#: TVR23-0094brbrVR License#: LIC23-0089brbrTOT#: 4690NbrbrbrbrThe Neighborhood:brbrLocated in a quiet residential area.brbrbrbrGetting Around:brbrUber/Lyft is available but wait times can vary.brbrbrbrOther Things to Note:brbrYou may also see this home listed as “Farmhouse - Pool, Hot Tub and Tastings Included” on some booking sites.
Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(13)

$2121.78

/ Nightly
Private Vacation Home

Dreamy A-Frame Luxury - Privacy - Views-Hot Tub

Healdsburg, California, United States

Summary:brbrBest Views in Healdsburg!brbrbrbrThe Space:brbrArchitecturally stunning, serving up world class views of Dry Creek Valley, Mayacama Mountains, and Fitch Mountain. Private country property yet a few minutes to downtown Healdsburg. brbrbrbrCentral to world famous wine roads... Westside Road, Dry Creek Road, and West Dry Creek Road. You have easy access to any vineyard or dining experience of your choosing.brbrbrbrExplore Sonoma County with some of the most picturesque drives on the West coast right outside your door. You’re at the crossroads of Dry Creek Valley and Russian River Valley and a quick jaunt to Alexander Valley. brbrbrbr- Large 40' Heated Pool set in the middle of towering redwoodsbrbr- Hot tub with magical views to the hills overlooking vineyards of Dry Creek Valleybrbr- BBQ with outdoor dining brbr- Outdoor Showerbrbr- Multiple Decks with outdoor loungebrbr- Poolside lounge with fire pitbrbr- Outdoor giant chess board and jenga brbr- Gourmet kitchen brbr- Washer & Dryer brbr- Self check in brbr- WIFI brbr- Massive windows with incredible views of the landscape overlooking gardens, fruit trees and towering redwoodsbrbr- 2 acres fully fenced and Privatebrbr- Great for Groups and FamiliesbrbrbrbrbrbrCapacitybrbr- 3 bedrooms w/2 King bedrooms en-suite and 1 Queen bedroombrbr- 1 guest suite with King bed en-suitebrbr- 1 loft in main house w/King bedbrbrThere's a Pull-Out Sofa in the living room and a Pull-Out Sofa in the primary bedroom for kids/teensbrbr*Max 8 adults* + 4 kids/teensbrbrAdditional charge after 8 peoplebrbrbrbrbrbr 2 minutes to Madrona Manor brbr 5 minutes to Healdsburg's Historic Plaza brbr 14 minutes to Russian River Brewing Company brbr 11 minutes to Dry Creek Vineyard brbr 4 minutes to Amida Winerybrbr 10 Dry Creek General StorebrbrbrbrbrbrPool HeatbrbrPool is heated during the summer months at no charge. Heating is offered from September 15th to May 1st for a daily fee of $150 (our cost is $200/day). Please provide at least 48 hours' notice in advance if you would like the pool to be heated before your stay. It is important to consider that heating the pool during off-season cooler temperatures may impact the maximum warmth the pool can reach.brbrbrbr- Fire Season brbrSonoma County does experience a fire season that may affect your stay. In line with the policy followed by hotels and other vacation rentals in our area, we will offer a full refund if our property in Healdsburg is under mandatory evacuation. However, if our house is not under mandatory evacuation, refunds will not be provided.brbrbrbr ** Due to this we recommend adding insurance to your stay so that you can receive a refund from the travel insurance provider if you need to cancel.**brbrbrbrGuest Access:brbrThe entire property is yours to enjoy.brbrbrbrThe Neighborhood:brbr5 minutes to Downtown Healdsburg and the square. Walk to town is 1 mile. Central to everything Sonoma Wine Country has to offer.brbrbrbrGetting Around:brbrWalk to Madrona Manor, nearby vineyards and downtown. A car will be necessary for other destinations. This location is splendid for touring on bicycle. .brbrbrbrOther Things to Note:brbrNo smoking in or around property.brbrbrbrInteraction with Guests:brbrWe are available via text or phone to answer any questions or offer suggestions. We're not far away and can be on-site for any additional help.
Bed 5

Bed

Bath 4

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(2)

$492.41

/ Nightly
Private Vacation Home

Riverfront Healdsburg Home, Private Dock

Healdsburg, California, United States

Summary:brbrStep onto your private dock and watch the Russian River slide past while oak-covered hillsides frame the view. Two stacked units — each with its own entrance, patio, and bathroom — make this riverfront stay work for two couples or a family of four. A bocce court, big yard, and canoe wait outside, and downtown Healdsburg's wineries and fine dining are 2.4 miles away.brbrbrbrThe Space:brbrStart your morning on the deck as light filters through the willows along the Russian River. Spend afternoons paddling from your private dock, or head out to taste at Aperture Cellars and Stuhlmuller. Come evening, light the grill on the patio and pour a bottle from one of the Healdsburg Plaza shops — downtown's tasting rooms and restaurants are 2.4 miles up the road.brbrbrbrStep into the upper unit where vaulted ceilings open over a sunlit living room, mid-century furnishings, and sliding glass doors that pull the forested river view inside. The layout flows easily between the lounge, dining table, and kitchen — and a telescope by the slider is ready for stargazing once Sonoma County skies darken.brbrbrbrCook at the quartz island with everything you need close at hand, then pull up a stool for casual meals at the bar. Open shelving keeps wine glasses within reach for that bottle you grabbed in town.brbrbrbrSlide downstairs to a fully self-contained lower unit with its own kitchenette, bathroom, and washer/dryer — the layout works for two couples who want their own coffee maker but want to share the dock and yard out front.brbrbrbrWake in the king bedroom under a whisper-quiet ceiling fan, with crisp linens and a built-in desk if remote work follows you here. The lower queen has its own bathroom and entry for added privacy.brbrbrbrOUTDOOR LIVINGbrbrCovered decks with wood-slat privacy screens stretch toward the river on both levels, framed by mountain and water views. Pull up an Adirondack chair in the yard, roll the bocce ball court for a pre-dinner match, or carry the canoe down to the private dock for a slow paddle. A gas grill makes riverside dinners easy.brbrbrbrSLEEPING ARRANGEMENTSbrbrSleeps 4 across two stacked units:brbr- Bedroom 1 (upper unit): King bed, ceiling fan, built-in deskbrbr- Bedroom 2 (lower unit): Queen bed, en-suite bath, kitchenettebrbrbrbrPROPERTY AMENITIESbrbr- Private river dock with canoe for guest usebrbr- Bocce ball court and large yardbrbr- Gas grill and covered riverfront decksbrbr- Limited air conditioningbrbr- Full kitchen (upper) plus kitchenette with washer/dryer (lower)brbr- High-speed Wi-FibrbrbrbrPlease note: this home sits directly on the Russian River, and during high-water events the lower unit can experience water intrusion.brbrbrbrGuest Access:brbrStep into modern architecture wrapped in wood-slat screens and covered outdoor living, mid-century inside, with a black hex-tile bathroom that anchors the look. The whole home is yours, with a BBQ, outdoor dining, an enclosed yard, and mountain and river views. Your check-in details land before your stay; pull into the driveway, with on-street as overflow.brbrbrbrThe Neighborhood:brbrYou're on the Russian River just minutes from downtown Healdsburg — one of Sonoma County's most celebrated food and wine destinations. The Healdsburg Plaza anchors the town with walkable tasting rooms, boutiques, and galleries. For dining, Valette (2.3 mi) offers refined, Sonoma-sourced cuisine. Bravas Bar de Tapas (2.4 mi) serves Spanish small plates on a lively patio. Journeyman Meat Co. (2.4 mi) is the spot for outstanding charcuterie and sandwiches. SingleThread (2.4 mi) is a three-Michelin-starred destination for a special-occasion meal. For wine, Stuhlmuller Vineyards (1.9 mi) and Sapphire Hill Winery (2.1 mi) offer intimate tastings nearby. Del Rio Woods Regional Park (0.1 mi) is steps from the property for a quick walk, and Healdsburg Veterans Memorial Beach (2.1 mi) provides river swimming in summer. Shelton's Natural Foods Market (2.3 mi) is the nearest full-service grocery.brbrbrbrGetting Around:brbrHealdsburg is about 75 minutes from San Francisco via US-101 North — a straight, scenic drive into the heart of Sonoma wine country. Parking for up to 3 vehicles in the driveway and on the street. A car is the easiest way to take in the three valleys that meet here — Dry Creek, Alexander, and Russian River. For tasting days, plan a designated driver or book a rideshare ahead — it makes the whole day easier.brbrbrbrOther Things to Note:brbrThis property is configured as two separate units — one bedroom, bathroom, and full kitchen upstairs, and one bedroom, bathroom, kitchenette, and laundry downstairs. They have separate exterior entrances connected by outside stairs. The home sits directly on the Russian River with a private dock and sit-on-top kayaks — please use water equipment responsibly and at your own risk. During high-water events the lower unit can experience water intrusion — this is uncommon but worth noting during winter storm season. The primary renter must be 21 or older. Exterior security cameras are installed.
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

Slider Thumb

$238.33

/ Nightly
Private Vacation Home

Stylish New Healdsburg Home - 3 Blocks to Plaza

Healdsburg, California, United States

Super location of this newly completed home is a 5 minute walk to downtown where there are wine tasting rooms, wonderful dining, bakeries, galleries, shopping, so close you don't even need a car. Big John's Gourmet Grocery/Deli store is also a short walk for all your picnic or in home dining needs.brbrThis home was designed for a relaxing stay and is tastefully decorated with your comforts in mind. The open floor plan as you enter is inviting with how light it is. The high ceilings make for a spacious feeling and the entry with hardwood floors and designer lighting along with Wine Country Art though out, lets you know you have arrived!brbr-Front Porch is covered and furnished with Wicker style loveseat, over sized chair, ottoman and table for your morning coffeebr-Dining area has a Boulangerie table with 6 leather chairs br-Kitchen is slab granite, with all stainless appliances and an Island with swivel bars stools for 4br-Living area has a plush leather sofa and chairs with Flat Screen 48' LED/HD Direct TVbr-Adjacent to the living area is a fenced in patio with table and umbrella that seats 6-8 There is a large Weber Gas Grill (plumbed in so you never run out of it) along with a cover and tools. Also has nice landscape with draughtt tolerant plants and globe patio lights for evening entertaining.br-Upstairs are 3 Bedrooms and LaundrybrThe Master Suite has a King bed, walk-in closet, over-sized shower and LED TV.brSecond bedroom also has a King bed brThird has twin beds with very comfortable mattresses brAll bedrooms feature ceiling fans, clocks, ample closet space, and luggage racks.brbrThe area in front of the home is attractively landscaped green space continuing the entire street and is the perfect location for touring all that Sonoma County offers; scenic coastline, Redwood Forest and close to other wine destinations and the Russian River. We hope you will enjoy the perfect blend of modern amenities and relaxing atmosphere we have created to make your stay memorable.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(6)

$652.44

/ Nightly
Private Vacation Home

Vinehaven - 3BD Healdsburg Retreat with Spa

Healdsburg, California, United States

Situated just two miles outside of downtown Healdsburg, this home serves as the perfect launch pad for exploring the vineyards of California's famed Dry Creek Valley. This 1600 sq ft retreat is beautifully furnished and decked out in vintage 50s architectural style. The private redwood deck is surrounded by a half-acre of landscaped gardens and boasts a brand-new, six-person Hotspring spa along with endless views of the vineyards and surrounding foothills. A grill and dining areas on the deck and in the garden offer plenty of opportunities for alfresco meals.brbrThe open plan layout, French doors, and beautiful oak flooring gracing this special home and create a spacious feel, with the large living room transitioning into the lovely dining area and a well-equipped kitchen with an island and double oven. Plantation shutters, crown molding, and recessed lighting add even more period charm.brbrThe romantic primary suite with garden and vineyard views is furnished with an oak sleigh with luscious linens. The en suite bathroom features a dark blue claw-foot tub and shower, as well as new, granite-topped vanity. The second and third bedrooms share a second bathroom with a large tiled walk-in shower and pedestal sink. A queen size sleeper sofa in the living room offers additional guests an extra bed.brbrEntertainment options include a 50-inch 4K ultra smart TV, Comcast cable, a DVD player, and high-speed WiFi with up to 600 mbps download speed!brbrThings to Knowbrbr• Check-in time: 4:00 p.m.br• Check-out time: 10:00 a.m.br• Quiet hours are from 9 p.m. to 7 a.m.br• No smoking is permitted anywhere on the premises.brbr• 2 dogs welcome in this home. No other animals are allowed without specific Beaux Maison approval.br• Parking notes: There is free parking available for 3 vehicles.br• Guest entry instructions: This rental utilizes an E-lock, a digital lock that requires a unique code to enter. This code is reset after each guest's stay.brbrLIC24-0042brTOT# 1685NbrbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrYou must be 25 years or older to rent this property.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb

$557.43

/ Nightly
Private Vacation Home

Healdsburg Dog-Friendly Vineyard Farmhouse and Hot Tub

Healdsburg, California, United States

Summary:brbrRows of Alexander Valley vines stretch to the hills right outside your door as you settle into this beautifully restored 1912 farmhouse on a working vineyard. Hardwood floors, crown moldings, and French doors frame a home that feels both timeless and effortlessly comfortable. A complimentary tasting at the on-site barn winery awaits, and Healdsburg's celebrated Plaza dining scene is just a short drive away. Pour a glass, sink into the hot tub, and let wine country come to you.brbrbrbrThe Space:brbrSpend mornings under the porch as vineyard rows catch the first light, afternoons among Healdsburg Plaza's tasting rooms and SingleThread, and evenings on the patio with a glass from the day's barrel-room visits.brbrbrbrFrench doors open from the living room straight to the deck and the vineyard panorama beyond; bamboo shades soften the afternoon light. A sofa and flat-screen anchor the main space, and an adjacent formal living room gives the group room to spread. The updated kitchen flows into a casual family room, while the formal dining room — rich wainscoting, pendant lighting — gathers six. The primary bath's clawfoot tub and marble vanity carry the Alexander Valley old-house mood all the way through.brbrbrbrOUTDOOR LIVINGbrbrMornings begin on the covered front porch. Move to the gravel patio for al fresco dining at the six-seat table, then end the day in the private hot tub with vineyard views stretching to rolling hills. A gas grill and lush gardens with mature palms complete the setting.brbrbrbrSLEEPING ARRANGEMENTSbrbrThree sleeping areas for up to six guests. The primary suite has a king bed with en-suite clawfoot tub, marble vanity, and walk-in shower. A second king sits on the main level, and the loft under skylights offers a third king.brbrbrbrPROPERTY AMENITIESbrbr-- Private hot tubbrbr-- Gas grillbrbr-- Central ACbrbr-- Smart lock entrybrbr-- Parking for 4 vehiclesbrbr-- Dog-friendly (1 dog, 25 lb max)brbrbrbrGuest Access:brbrDrop into the private hot tub on a deck looking out over your own vineyard view — two separate buildings give the property room to spread out. You've got the whole estate, dogs welcome, with a clawfoot tub, BBQ, outdoor dining, and an enclosed yard. Punch in the keypad code at the door; ample parking waits inside the gate.brbrbrbrThe Neighborhood:brbrThe property sits in the heart of Alexander Valley, one of Sonoma County's premier Cabernet Sauvignon regions. Banshee Wines (0.4 mi) is just down the road for an easy visit. Within a mile or two you'll find Stonestreet Winery (1.2 mi) and Robert Young Estate Winery (1.2 mi) — both acclaimed producers with beautiful grounds. Medlock Ames Historic Healdsburg Tasting Room (0.9 mi) and Hawkes Wine (0.9 mi) are also nearby. Jimtown and Then Sum (0.9 mi) is a local favorite for a casual bite or morning coffee. Francis Ford Coppola Winery (3.1 mi) offers dining, wine tasting, and a pool in a grand setting. For hiking, Healdsburg Ridge Open Space Preserve (2.9 mi) has serene trails with wildlife viewing. Dog owners will appreciate Villa Chanticleer Dog Park (3.8 mi) for an off-leash run. Downtown Healdsburg and its celebrated Plaza — with walkable tasting rooms, galleries, and farm-to-table restaurants — are roughly 4 to 5 miles south.brbrbrbrGetting Around:brbrHealdsburg is about 75 minutes from San Francisco via US-101 North — a straight, scenic drive into the heart of Sonoma wine country. Ample on-site parking for up to 4 vehicles. A car is the easiest way to take in the three valleys that meet here — Dry Creek, Alexander, and Russian River. For tasting days, plan a designated driver or book a rideshare ahead — it makes the whole day easier.brbrbrbrOther Things to Note:brbrThis is a working vineyard — depending on the season you may see vineyard workers tending the vines, which is part of the authentic Alexander Valley experience. The primary renter must be 21 or older. One dog is welcome (25 lb max). Your stay includes a complimentary wine tasting at the adjacent barn tasting room — details are provided at check-in. Summer highs can exceed 90°F in Alexander Valley, but the home has central air conditioning. Guests are asked to be mindful of the vineyard and gardens — please stay on paths and patios.
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(16)

$958.75

/ Nightly
Private Vacation Home

Healdsburg Escape Free Wine Tasting Close to Plaza

Healdsburg, California, United States

The spacebrStaying with Away2Vacay you will find yourself in the heart of wine country with rolling hills of grapevines and green pastures when you make your way to Healdsburg. With lush gardens and a secluded feel, Maison Cachée will welcome you with a peaceful ambiance that will spoil each lucky guest in no time. And, when you want to venture out a bit, a plethora of shops, restaurants, and grocery stores are mere minutes from your front door in downtown Healdsburg. Oenophiles will love one extra-special perk at this home - when making reservations, guests can receive various discounts and savings at several local wineries like Ridge, Wilson, Mazzocco, Matrix, and Rock Pile. Further details regarding the perks will be provided at the time of your booking confirmation.brbrWhen everyone returns from various adventures, the interior has two wonderfully furnished living areas to gather in and a well-equipped kitchen just waiting to assist with preparing tasty homecooked meals. The accommodating dining table will be great for formal meals inside, yet the summer breeze will be calling your name for alfresco dining on the furnished deck. When you want to keep things casual, fire up the gas grill and throw on some burgers and dogs as the sun dips behind the treetops.brbrThis special retreat is just waiting to create unforgettable memories, so make your way to this Northern California gem today!brbrThe home has 2 twin size roller beds located in the master bedroom closet. Sheets and comforters are located in the upstairs hallway closet.brbrOther things to notebrNetflix, Hulu, Disney+, HBO, etc. streaming are available (guests need their own account).brbr2 dog(s) are welcome in this home for a $150 pet fee. No other animals are allowed without specific approval.brbrParking notes: There is free parking for 4 vehicles. Parking is located in the driveway.brbrSecurity camera details: There is a ring doorbell on the front door.brbr***The indoor fireplace is out of service and should not be used***brbrOur property is set in the countryside in the beautiful Dry Creek Valley. It's not unusual to come across bugs, spiders, ants, etc. Our home is treated by a pest control company on a monthly basis as a deterrent.brbrCounty permit number: TVR22-0027brbrCounty tax number: 4272N
Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps

Slider Thumb
Exceptional(58)

$745.94

/ Nightly
Private Vacation Home

Spectacular Vineyard View!! SPA, Close to Plaza!- 3br/2ba (up to 8 guests)

Healdsburg, California, United States

Shaded by a 100-year-old oak tree, this very special home ‘lives’ on 30 vineyard acres and is off Dry Creek Road, just one mile west of the north end of charming, upscale, historic, Healdsburg in the heart of Sonoma County’s Wine Country. Newly renovated, this 3 bedroom/2 bath, Ranch House with central heat/AC is beautifully landscaped and decorated with European styling, wall paper, draperies, clean Scandinavian lines, and warm wood flooring throughout, and newly landscaped backyard with Sundance Spa.brbrEnter and enjoy the open flowing floor plan with the living room area to your left and the dining area to the right, and the kitchen just beyond.A decorative fireplace with candelabra, sleeper sofa (full size), 2 leather chairs, and a lovely area rug with coffee table, grace the living room; entertainment is provided by the Sharp LCD HD 26” wide screen TV with a Sony HD DVD player and a Panasonic compact audio system with CD, cassette, and radio.brbrThe dining area with beautiful built-in floor to ceiling cabinets, is a warm, welcoming, and wonderful space for sipping, supping, and good conversation, and the dining table expands to seat 8+, with 2 more spaces at the counter. All new kitchen cabinetry (one is lighted with glass shelves and doors), black granite counter tops and all new GE stainless steel appliances, contribute to a wonderful cooking experience.brbrYour chef will enjoy using the very efficient ceramic cooktop with oven below and a built-in microwave-exhaust vent combo above; the fridge, dishwasher and large stainless steel double sink complete this very efficient and well designed kitchen..brbrA short hallway leads to the master suite with a luxurious king bed, wood floors and area rug, vineyard views, and a newly redone ensuite bathroom with a granite topped vanity and large beautifully tiled shower. The second and third bedrooms are also wood floored, one with two double beds and one queen bedroom.brbrWhen also using the living room double sleeper sofa, ‘Big Oak’ can accommodate as many as 8 guests, if you do not mind getting cozy with family and/or friends, although ideally suited to smaller gatherings. The lovely second shared bath also has a granite topped vanity and a tastefully tiled large shower to facilitate preparing for your dates!brbrBeautifully landscaped, the front yard, shaded by the Big Oak, has two lawn areas, abundant plantings & shrubs, and a front porch seating area to watch the world go by. Leading to the 2-car garage, is a large driveway and the backyard is fenced with acres of vineyards just beyond and a back patio with table and chairs, umbrella, and a Wolf propane BBQ for your grilling pleasure (a Weber briquette grill is also available for the ‘kingsford’ purists). Enjoy the Sundance Spa in the newly landscaped backyard.brbrThe Big Oak Vineyard House is very conveniently located and a great ‘home base’ for exploring the diversity of Sonoma County Wine Country. Only minutes away from Healdsburg, the ‘crown jewel’ of our ‘Tuscany’ in northern California, you will need plenty of time for wine tasting, fine dining, shopping, art & antique galleries, and enjoying the Russian River with many more adventures nearby.brbrIn addition to overlooking the beautiful vineyard of West Wines, the West Wines Tasting Room is just next door to the home for an up close and personal wine tasting experience.brbr**Sonoma County Ordinances requirements are as follows**brbr• Maximum occupancy, not including children under 3, is 8br• Maximum number of vehicles allowed is 3br• Quiet hours must be observed between 9:00 p.m. and 7:00 a.m.br• Outdoor amplified sound is not allowed br• The Transient Occupancy Tax Certificate number is 1669NbrbrPlease help us preserve the serenity of the area and keep us in compliance with the ordinances. Thank you and we hope you enjoy your stay!brbrPet Policy: only small lapdogs are considered on this property because of soft wooden flooring. Please contact us for special circumstances!
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(6)

$275.33

/ Nightly
Private Vacation Home

Urban Elegance in Wine Country: Unwind Just Steps from Healdsburg Plaza!

Healdsburg, California, United States

Settle in and live like a local at our beautifully remodeled single-level retreat—available exclusively for stays of 30 days or more. Perfect for remote work, relocation, or an extended wine-country escape, this home blends refined comfort, modern design, and unbeatable walkability—just three short blocks from Healdsburg Plaza, the heartbeat of Sonoma County’s world-renowned wine region.brbrFrom the moment you arrive, you’ll feel the calm sophistication that defines Urban Elegance in Wine Country. Tucked away on a quiet residential street yet steps from Michelin-starred restaurants, artisanal bakeries, and cozy tasting rooms, our home offers the best of both worlds: privacy and proximity. Wake to the sound of birds and the scent of nearby vineyards, then stroll downtown for coffee, yoga, or the Saturday farmers market. End your evenings with live music in the Plaza or a glass of pinot on the deck beneath the Sonoma sky.brbrA Space Designed for Long-Term ComfortbrbrOur home has been thoughtfully designed for extended stays—where comfort, practicality, and aesthetic meet. Every finish and furnishing was selected to create a sense of effortless luxury, from the soft lighting and high-end linens to the open layout that invites natural light throughout.brbrTwo Bedrooms & Two Bathsbrbr- Primary Suite: A king-size bed with a plush, hotel-quality mattress and crisp white linens invites deep rest. The ensuite bathroom feels like a private spa, complete with double vanities, a walk-in European-style glass shower, and premium bath amenities. A large walk-in closet provides generous storage for clothing, luggage, and longer-term needs.brbr- Guest Bedroom: The guest room features a queen-size bed, elegant decor, and easy access to a full bath with a shower/tub combination—ideal for visiting family, friends, or colleagues.brbrGourmet Kitchen & DiningbrbrAt the heart of the home, the fully equipped gourmet kitchen makes cooking a pleasure, whether you’re preparing quick breakfasts or multi-course meals. Enjoy a five-burner gas range, farmhouse sink, and GE stainless steel appliances—including a full-sized refrigerator, dishwasher, and microwave. Every utensil and appliance is on hand for the modern chef. Slide open the glass door to the outdoor deck, where you’ll find a gas grill and dining space perfect for alfresco meals under twinkle lights or a canopy of stars.brbrLiving Area & Work-Friendly DesignbrbrThe open-concept living room invites you to unwind in style. Relax by the charming fireplace, stream your favorite shows on the Smart TV, or curl up with a glass of cabernet after a day exploring wine country.brFor those working remotely, the home offers fast, reliable Wi-Fi, and flexible workspaces—whether you prefer the dining table with natural light or a quiet corner desk setup ideal for video calls and productivity.brbrConveniences for Longer StaysbrbrEvery element of the home was created with longer visits in mind. You’ll appreciate:brbr- In-unit washer and dryer for easy laundry carebrbr- Central heating and air conditioning for year-round comfortbrbr- Ample storage for luggage, groceries, and personal itemsbrbr- Private driveway parking and quiet neighborhood surroundingsbrbr- Smart home touches, from lighting to streaming, making your stay seamlessbrbrWhether you’re in Healdsburg for a corporate assignment, a creative sabbatical, home renovations, or simply an extended getaway, our retreat provides a turn-key solution that feels like home.brbrOutdoor LivingbrbrThe outdoor deck and garden area provide a tranquil extension of your living space. Enjoy morning coffee surrounded by lush landscaping or evening wine as the sun sets over the oaks. With privacy fencing, comfortable lounge seating, and soft outdoor lighting, it’s an ideal spot to relax or entertain small gatherings.brbrLocation, Location, LocationbrbrThis home’s location is what truly sets it apart. Situated in a quiet residential enclave, you’re just minutes on foot from:brbr- Healdsburg Plaza’s restaurants, wine bars, and boutique shopsbrbr- Weekly farmers markets and summer concerts in the Plazabrbr- Foss Creek Pathway and local parks for walking, jogging, or cyclingbrbr- Dozens of wineries across Dry Creek, Russian River, and Alexander Valleybrbr- Convenient access to Highway 101 for day trips to Geyserville, Calistoga, or SonomabrbrLive like a local—shop at Big John’s Market, pick up pastries from Costeaux French Bakery, or spend afternoons wine tasting at nearby Jordan, Ridge, or Ferrari-Carano. Every experience of Healdsburg’s charm is within reach, without the need to drive far.brbrLifestyle & ExperiencebrbrOur guests often describe their stay as transformative. Many arrive for a month and wish they’d stayed longer. Whether you’re a couple seeking a romantic extended retreat, a family on relocation, or a professional working from the wine country, you’ll find the home to be peaceful, inspiring, and meticulously maintained.brbrEvery design element—from the neutral color palette and curated art to the balance of natural wood and soft textiles—was chosen to create serenity. This isn’t just a rental; it’s a home for living, creating, and restoring.brbrGuest Access & Stay DetailsbrbrYou’ll have full private access to the entire home and outdoor spaces.brbr- Minimum stay: 30 nights (per City of Healdsburg requirements)brbr- All utilities, high-speed internet, and landscaping services are included in your rate.brbr- Housekeeping during your stay can be arranged upon request.brbr- Sorry, no pets or smoking are permitted.brbrOur Commitment to ExcellencebrbrWe take pride in offering a spotless, professionally maintained property that exceeds expectations. Our guests frequently comment on the cleanliness, thoughtful amenities, and attention to detail that make their extended stay effortless. We’re available throughout your stay to answer questions, assist with local recommendations, or help arrange services like wine tours, in-home chef experiences, or cleaning schedules.brbrYour Extended Stay AwaitsbrbrEscape to the serenity of wine country living—where your mornings begin with sunlight streaming through the kitchen windows and your evenings end with laughter on the deck beneath the stars. Here, every day brings a new adventure, and every night welcomes you home to tranquility.brbrBook your extended stay today and experience the best of Healdsburg living—where luxury meets comfort, and convenience meets authenticity. Discover why our guests return year after year to their home away from home in Sonoma County.
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(24)

$3703.81

/ Nightly
Private Vacation Home

Spectacular View Estate 5min Away

Healdsburg, California, United States

This is a unique & spectacular 12 acre View estate nestled in the heart of Dry Creek/Lytton Springs wine country. Home to Dudley Vineyards an estate grown, small production fine wine. Only 5 minutes from the Healdsburg town center. This rolling vineyard ranch view estate has it all. The pool & hot tub are surrounded by great flagstone with big views of Mt. Saint Helena, full size Bocce court, out door fire pit with 32 speakers through all the outdoor and indoor areas of the property. Big yard with panoramic views allows for the perfect space to relax & enjoy. Plenty of outdoor furniture to lounge & umbrellas for shade if so desired. brbrRecently remodeled this 5 bedroom & 4.5 bath (4 Full and 1 Half Powder Room) home is well designed to flow from indoor to outdoor living. (There are 5 beds. 6 if you count the pull-out. 1 king in master, 2 queens in separate guest rooms, 2 twins in one guest room (these are bunk beds) and an extra sofa pull-out full size bed in the extra 5th bedroom/bonus room off of the master). One of the queen bedrooms is a private in law unit with a separate entrance outside that can be accessed off of the kitchen in the main house. Folding Nana doors open the whole living rm out to the outdoor space - which also has 35,000 BTU heaters for your enjoyment if it gets cold at night. And a large BBQ. Living room has an old Baby Grand Steinway piano. (model A - real ivory keys!)brKitchen is designed for cooking & entertaining! With 3 separate fridges, (one designated just for wine), 6 burner stove, 3 separate Bosch dishwasher, 2 Miele ovens, 2 sinks...A fully stocked kitchen complete with a full 27 piece set of All-Clad pots & pans, large KitchenAid blender, large KitchenAid coffee maker, etc. Everything one needs to properly maximize the culinary experience while there. There are speakers throughout connected to a Sonos system which can be controlled through an iPhone. High-speed (10mps) wifi is throughout the home. As well as New HD Smart TV (with Dish) with all the premium channels.brbrThis special property pretty much has it all & is just minutes from Healdsburg town center (which has some of the best restaurants of all Sonoma & Napa valleys).brbrPets will be considered on a case by case evaluation for an additional fee.
Bed 4

Bed

Bath 1

Bath

Sleep 12

Sleeps

Slider Thumb
Exceptional(105)

$1248.47

/ Nightly
Private Vacation Home

Hidden Pocket: Pool + Spa, Private Retreat, 1.5 Fenced Acres, Healdsburg

Healdsburg, California, United States

Welcome to Hidden Pocket: The Perfect Wine Country EscapebrbrTucked away at the end of a quiet country road on 1.5 private fenced acres, our resort-style sanctuary offers the ultimate Sonoma Wine Country experience. Enjoy complete privacy and room to roam while being just 10 minutes from vibrant Healdsburg Plaza, world-class wineries, acclaimed restaurants, and boutique shopping.brbrWith over 100 five-star reviews, our guests consistently tell us: We didn't want to leave! Discover why families, wine enthusiasts, and groups return year after year to this peaceful retreat.brbrYour Own Wine Country EstatebrbrThe 1.5 fenced acres give you true resort-style privacy—room for kids to play, dogs to explore safely, and adults to completely unwind. The extensively landscaped grounds create a peaceful sanctuary where you can disconnect from daily life and reconnect with what matters.brbrYour Private Resort ExperiencebrbrStep into your own personal wine country resort, where indoor luxury meets outdoor paradise. Enjoy our solar-heated pool (mid-April through October, weather permitting) surrounded by lush landscaping. Relax in our premium 6-person stainless steel spa, available year-round for evening relaxation under the stars. Unwind in the shaded outdoor living room nestled under a pergola beside our thriving vegetable and flower garden—feel free to pick fresh herbs and vegetables during your stay!brbrEntertain at our poolside dining area with table seating for eight and six chaise lounges for soaking up the California sunshine. Active guests will appreciate our basketball hoop and easy 3-mile bike ride to Healdsburg Plaza along quiet country roads.brbrElegant Interior Living SpacesbrbrInside, luxury and comfort await in every thoughtfully designed space. The gourmet chef's kitchen features sleek stainless steel appliances, Caesarstone countertops, and everything needed for culinary adventures. Wine enthusiasts will appreciate our lead-free crystal glassware and dishwasher-safe decanters—perfect for enjoying your winery finds. Experience seamless entertainment flow from the spacious dining room with seating for eight into the cozy den.brbrRestful AccommodationsbrbrEach sleeping space offers premium comfort and privacy for up to 8 guests. The master suite features a king bed with spa-like ensuite including double vanity, whirlpool tub, and separate shower. Two additional queen bedrooms each offer custom Elfa closet storage and room-darkening shades. The living room includes a queen sleeper sofa for flexible sleeping arrangements. Convenient bathroom access includes a shared hall bathroom with shower/tub combo and dual vanity, plus an additional half bath.brbrModern Entertainment & ConveniencesbrbrEnjoy state-of-the-art technology throughout your stay. The den features a modern sectional with 43 Sony 4K TV. The living room offers a 75 Sony 4K TV with immersive 7.1 surround sound home theater. Entertainment includes 4K Blu-Ray players, DirecTV streaming, and a collection of family board games and movies. Lightning-fast WiFi (500+ Mbps) is available throughout the property—perfect for streaming and remote work.brbrStay comfortable year-round with central air conditioning and heating. Electric vehicle owners will appreciate our Tesla Universal Wall Connector (NACS/J1772 EV charger) available during off-peak hours (midnight to 3 PM). A front-loading LG washer and dryer makes extended stays convenient. We also provide curated local resources including Sonoma County travel guides and cookbooks to help you plan the perfect wine country adventure.brbrProperty PoliciesbrbrTo maintain our peaceful retreat atmosphere for all guests, we have the following policies: brbr- Strictly no smoking anywhere on the property br- No parties or eventsbr- Dogs permitted only with advance owner approval (cannot be left unattended)br- Property access limited to vehicles minivan-size or smallerbr- Quiet hours 9 PM to 7 AM per county regulations; no outdoor amplified soundbr- Maximum 8 overnight guests; total guests including daytime visitors not to exceed 14 per county regulationsbr- Signed rental agreement required within 48 hours of booking; Pool/spa waiver required for guests under 18br- For security purposes, outdoor security cameras are located by the gate and entry doors (no interior cameras)brbrPerfect ForbrbrFamily gatherings, couples' wine tasting weekends, milestone celebrations, or friends exploring Sonoma's renowned vineyards together. Our guests love the combination of complete privacy, resort-style amenities, and convenient access to everything Healdsburg and Sonoma County offer.brbrBook with ConfidencebrbrTransient Occupancy Tax Certificate Number 808NbrbrJoin our community of happy guests who've given us over 100 five-star reviews. We look forward to hosting you at Hidden Pocket!
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(20)

$1267.82

/ Nightly
Cottage

Heart of Healdsburg Cottage for 4, Pool, Spa, Fire Pit, WIFI, BBQ

Healdsburg, California, United States

The Heart of Healdsburg Cottage is a one acre property with an in ground pool, hot tub, hobby vineyard, and walking distance to wineries and the downtown plaza square. Because it is close in, the road is busy (access to the Russian River communities via Westside Road), however the back yard space creates a nice buffer from the traffic. The outdoor seating area offers lounges at poolside and a beautiful picnic table under the fairy lights strung above in the walnut tree. A large deck and hot tub sits outside the French doors entering the kitchen and a beautiful glass fire pit just beyond the deck.brbrThis lovely little cottage is really a unique and hard to find category for a few guests or 2 couples. Two bedrooms each have a queen bed with comforters, and robes are provided for each guest. A fireplace insert creates ambiance in the evenings, and a large modern kitchen stands ready for even the most discerning of chefs.brbrWestside Road is a popular bicycle route with a loop through the Dry Creek Valley, where in season you may stop at one of several farms available to visit and dozens of wineries waiting to host you for a tasting. Walk to downtown, less than one mile from the house, for shopping, gourmet treats and world class restaurants, tasting rooms and breweries. True West Film Center offers first run films and studies in the classics, and the galleries in town present many artists and their interpretations of our beautiful wine country.brbrThis beautiful cottage is ready for you to create new memories!brbrLIC24-0365brbrPlease note: When booking this home, an additional contract will be sent to you and must be signed to confirm your stay with us.
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(22)

$2684.32

/ Nightly
Private Vacation Home

Riverstone Estate sleeps 12 Pool Bocce Spa

Healdsburg, California, United States

Riverstone Estate is a private, Wine Country retreat located just minutes from downtown Healdsburg in Sonoma County. Set on a gated Russian River–side property, this historic estate offers more than 5,300 square feet of living space, three separate homes, eight bedrooms, and nine-and-a-half bathrooms, making it an exceptional destination for extended family gatherings, wedding groups, multi-generational vacations, and Wine Country adventures with friends. The estate accommodates up to 12 guests to select any combination of five bedrooms, each featuring its own private bathroom for comfort and privacy.brbrDesigned as a family compound, Riverstone Estate blends vintage Wine Country elegance with modern amenities. The property includes a seasonal in-ground pool, solar-heated from May through September, along with a year-round hot tub, fire pit, bocce ball court, horseshoe pit, basketball hoop, badminton/volleyball lawn, ping pong table, frisbee golf area, and a fully equipped exercise room. These resort-style features create a private, immersive experience comparable to a boutique resort—yet exclusively reserved for your group.brbrThe estate consists of three distinct homes thoughtfully arranged around beautifully landscaped grounds filled with gardens brimming with flowers and vegetables, fountains, mature trees, and peaceful seating areas:brbrQueen Anne House (3BR/4BA): This is the largest residence, featuring a gourmet kitchen with island, granite counters, and high-end appliances. Guests enjoy a formal dining room, a classic living room with hardwood floors, and an outdoor patio with grill and firepit for al fresco dining.brbrThe Coop (2BR/2BA): A cozy and comfortable cottage with two queen bedrooms, two full baths, a kitchenette, and a small living area—ideal for couples or guests seeking a quiet retreat within the estate.brbrOak Tree House (3BR/3BA): This home provides a full kitchen, living room, and multiple outdoor seating areas, including a deck and small terrace. The primary suite has an ADA-compliant bathroom and ramp access, offering accessibility for guests who appreciate or require it.brbrRiverstone Estate is known for its serene setting, Russian River views (no water access), and beautiful brick patios with outdoor seating. Guests enjoy cable ready high-speed WiFi, multiple kitchens, and spaces designed for gathering, cooking, celebrating, and relaxing. Wildlife, stargazing, and quiet natural moments are common throughout the stay.brbrLess than two miles from Healdsburg Plaza, the estate offers fast access to world-class wineries, farm-to-table dining, boutique shopping, cycling routes, and outdoor activities throughout Alexander Valley, Dry Creek Valley, and the Russian River Valley. Its proximity and privacy make it a rare find for travelers seeking an elevated Wine Country vacation.brbrRiverstone Estate is frequently chosen for wedding groups, milestone celebrations, extended family trips, and wine-focused getaways due to its size, flexibility, amenities, and unmatched privacy. Guests value the feeling of having an entire private resort to themselves, with activities and comforts for every age group.brbrPermit ZPE12-0027. Minimum age to reserve: 33.
Bed 5

Bed

Bath 6

Bath

Sleep 12

Sleeps

Slider Thumb
Exceptional(41)

$625.83

/ Nightly
Private Vacation Home

Riverside Cottage: Access and River Views- 1 miles from downtown Healdsburg

Healdsburg, California, United States

Perched above the Russian River on S. Fitch Mountain, this beautifully updated 1927 vintage river home offers the perfect blend of historic charm and modern comfort. With stunning river views, central heat and AC, and new dual-paned windows, this home is a serene escape just minutes from downtown Healdsburg.brbr✨ Home Highlights:br✔ Breathtaking River Views – Enjoy nature’s beauty from the spacious river porch, accessible through full-paned sliding doors.br✔ Modern Comforts – High open-beamed ceilings, central heating/AC, and upgraded windows maintain warmth and efficiency.br✔ Private Parking – Off-street parking for two vehicles.br✔ Seasonal River Access – Launch a kayak or take a dip from the property or walk just 5 minutes to the Del Rio Woods river access with picnic tables.br✔ Work & Relax – A dedicated workspace with highspeed WiFi ensures you stay connected while enjoying a peaceful retreat.brbr Unbeatable Location:brLocated in the heart of wine country, Healdsburg is a world-class destination at the meeting point of the Russian River, Dry Creek, and Alexander Valley wine regions. Enjoy award-winning wineries, fine dining, art galleries, boutique shopping, and spa experiences. Outdoor lovers can explore nearby hiking trails, biking routes, golf courses, and the stunning Northern California coastline.brbr Perfect for a relaxing getaway or an extended stay in one of California’s most sought-after destinations!brbr book today—this gem won’t last long!
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Home Most popular vacation rentals in Healdsburg