Vacation Home Rentals By Owner In Healdsburg, CA

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

Healdsburg Escape Free Wine Tasting Close to Plaza

Healdsburg, California, United States

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Bath

Sleeps

$745.94

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!

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

Healdsburg, California, United States

Bed

Bath

Sleeps

$275.33

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.

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

Healdsburg, California, United States

Bed

Bath

Sleeps

$325.0

This is a fully furnished home available for 30 day and longer stays.brbrImmaculately kept home 7 blocks from the plaza. Beautiful artwork adorns the walls and the living room has a large library. brbrTennis courts a 2 blocks away and the golf course is 2 minute drive to the club house. River access, bike and canoe rentals are available as well. brbrThe beautifully landscaped back yard has a deck area of the kitchen and a trellis covered dining area. A Weber Genesis grill is also on the deck.brbrThe house is 2 stories, but has ADA access and an ADA bath on the ground floor. Off street parking with an EV charge station.

Beautifully appointed house and garden only 10 minutes walk from the plaza

Healdsburg, California, United States

Bed

Bath

Sleeps

$3703.81

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.

Spectacular View Estate 5min Away

Healdsburg, California, United States

Bed

Bath

Sleeps

$1248.47

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!

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

Healdsburg, California, United States

Bed

Bath

Sleeps

$2684.32

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.

Riverstone Estate sleeps 12 Pool Bocce Spa

Healdsburg, California, United States

Bed

Bath

Sleeps

$625.83

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!

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

Healdsburg, California, United States

Bed

Bath

Sleeps

$410.67

Featured in California Home and Design, this stunning 3 bedroom, 2.5 bathroom retreat features 12' ceilings throughout, French doors, beautiful French oak hardwood floors & ultimate craftsmanship throughout. Just a 9 minute walk to Healdsburg Square, this home is appointed with iconic modern furnishings and beautiful antique furniture, art and accessories. brbrThe entrance is highlighted by an antique French door flanked by tall hedges. The entire property is encircled by lattice fences, hedges, luxuriant vines, and fruit trees providing unparalleled privacy and greenery. A large covered front porch provides ample room with furnishings for socializing or dining. The eight foot tall glass front door leads into an imposing great room.brbrThe light filled main space includes a generous living room with spacious sectional and large screen tv as well as a dining area highlighted by a Saarinan table and eight Maxima dining chairs by William Sawaya. The chef’s kitchen features a large integrated Thermador fridge/freezer, a Bertazzoni range and a Bosch dishwasher. A closet off the kitchen conceals an Asko washer and dryer. The kitchen is fully equipped with glasses, china, silverware, knives, Kitchen Aid mixer, Cuisinart, Oster blender, Nespresso coffeemaker, and a full complement of cooking tools. Pre-dinner champagne or cocktails can be enjoyed on barstools at the kitchen counter adjacent to the dining area.brbrEnjoy a seamless indoor/outdoor experience stepping through the French doors in the dining room to an outdoor eating area nestled under a large tree. Alfresco meals can be served on the huge vintage round glass table with matching curved bench and chairs. A lounging area abuts the dining area.brbrThe primary home features two principal bedrooms, each with king beds and an en-suite bathroom; one with very large tub/shower and heated bidet/toilet, the other with a shower. Both bedrooms include ample closets, plush bedding and a comfortable reading chair with lamp and bedside tables with lighting. Residence includes plush robes and bath amenities. One bedroom enjoys French doors onto the back patio.brbrAt the rear of the home is a small study with dedicated workspace and half bath. French doors open to the back porch and more lush greenery. Steps away, nestled in an old Meyer lemon tree, is a charming casita with a double bed, armoire, seating and desk with heating and air conditioning. This charming cottage can sleep one, or two cuddlers. Please note that there is no attached bath. Those sleeping in the casita can use the powder room in the main residence. The casita includes French doors with a beautiful view of the garden.brbrSummary:brbr-Luxurious residence with 3 bedrooms (one in separate casita), 2 and one half bathsbr-Fully equipped chef’s kitchenbr-Outdoor propane gas grillbr-Washer/dryerbr-Seamless indoor outdoor living with two outside dining and lounging options, one of esch coveredbr-Central heat and air conditioning in both main house and in casitabr-Two car off street parkingbr-Ramp from parking to front door for mobility impaired as well as threshold free floor planbr- Ten minute walk to the Square, five to famed Quail and Condor bakery and adjacent tasting roomsbrbrThe NeighborhoodbrbrOne block from the miles long Foss Creek Pathway dedicated exclusively for biking and walking. A short walk to Memorial Beach for swimming, kayaking, canoeing and picnicking. Local wineries with curated wine tastings are approximately a 5 minute walk from your front door.brbrDine in one of Healdsburg’s many prized restaurants, including two Michelin starred favorites. Healdsburg and nearby towns boast rich programs of monthly year-round wine events; jazz and musical events; art galleries and shows; famous running and cycling competitions (e.g., Amgen race and Grand Fondo, and the Fitch Mountain foot race); river races and festivals; craft beer shows (Sonoma County has 22 craft breweries), a Farmers Market (Saturday mornings, 9-12; Tuesdays, 4-6pm, May-Nov); and a multitude of farms that supply the best restaurants in Northern California. Healdsburg’s public golf course is a few minutes away.brbrVisit some of Healdsburg’s dozens of tasting-rooms downtown, or visit the wineries in nearby Dry Creek Valley, Alexander Valley, Russian River Valley, Chalk Hill, and Sonoma Valley.brbrWe are an hour and a quarter to San Francisco and 15 minutes from the Santa Rosa airport.

Wine Country Getaway - Healdsburg, Sonoma

Healdsburg, California, United States

3

Bed

Bath

Sleeps

$220.62

Summary:brbrSoak in the hot tub as Russian River views, vineyards, and rolling hills stretch toward Fitch Mountain itself — this 1940s Camp Rose cottage sleeps 4, with a semi-private community beach a half-mile downhill and Healdsburg Plaza tasting rooms two miles away.brbrbrbrThe Space:brbrSpend mornings with Nespresso on the deck as light catches the Russian River below, afternoons walking the half-mile down to Camp Rose's semi-private community beach or the public Del Rio Woods access a mile up the road, and evenings two miles away in downtown Healdsburg among the tasting rooms, vineyards, and restaurants around the Plaza.brbrbrbrSettle into the sectional in the sunny living room, where a stone hearth anchors the space and wall sconces throw warm light across the hardwood — a comfortable spot to plan tomorrow's run at Dry Creek Vineyard, Trentadue Winery, or Kendall-Jackson Wine Estate & Gardens.brbrbrbrCook in the vintage-style kitchen stocked with the essentials and a Nespresso maker, then linger at the dining table as a wall of windows pulls the hillside and river valley right to your plate. A pass-through window keeps the cook in the conversation, and the attached laundry room with washer/dryer makes longer stays easy — handy after a day at Armstrong Redwoods, Safari West, or the Luther Burbank Center for the Arts.brbrbrbrOUTDOOR LIVINGbrbrStep onto the expansive deck for your private hot tub overlooking the Russian River, vineyards, rolling hills, and Fitch Mountain itself. Pull up a chair at the outdoor dining table, sink into the comfortable sitting area furniture, or claim the hanging egg chair for an afternoon book — horizontal wood fencing and mature trees keep it all feeling private.brbrbrbrSLEEPING ARRANGEMENTSbrbr- Bedroom 1: King bed plus twin trundlebrbr- Bedroom 2: Twin bedbrbrSleeps 4 across 1 bathroom.brbrbrbrPROPERTY AMENITIESbrbr- Private hot tub with Russian River, vineyard, and Fitch Mountain viewsbrbr- Expansive deck with dining table, sitting area, and hanging egg chairbrbr- Full kitchen with Nespresso coffee makerbrbr- Washer and dryer in attached laundry roombrbr- One designated driveway parking spotbrbrbrbrThe home is subdivided into two units; your unit sits 5–6 steps down from the street-level driveway.brbrbrbrGuest Access:brbrSettle in by the floor-to-ceiling stone fireplace, then drift out to the deck and the private hot tub for the long valley view. You've got the whole cottage, with a hammock, outdoor dining, and vintage red-and-cream checkerboard floors in the kitchen. Grab the key from the lockbox; one designated drive spot, plus one usually-open on-street spot — neighborhood parking is tight.brbrbrbrThe Neighborhood:brbrPerched on the slopes of Fitch Mountain in the historic Camp Rose neighborhood, you're perfectly positioned to explore Healdsburg's wine country treasures. Walk just half a mile downhill to reach the semi-private Camp Rose beach access on the Russian River — exclusively for neighborhood residents. For more river fun, Del Rio Woods Regional Park (0.5 miles) offers public beach access and trails. The renowned Fitch Mountain Park & Open Space Preserve Trailhead (0.9 miles) provides hiking with panoramic valley views. Downtown Healdsburg's charming Plaza lies just 2 miles away, home to SingleThread Farm Restaurant (2.0 miles), Bravas Bar de Tapas (2.0 miles), and Valette (1.9 miles). Stock up on organic groceries at Shelton's Natural Foods Market (1.9 miles) or grab artisan sandwiches from Journeyman Meat Co. (2.0 miles). Wine tasting rooms line the Plaza, while the actual vineyards of Dry Creek Valley, Russian River Valley, and Alexander Valley fan out within a 15-minute drive.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. You have one designated parking space in the driveway, plus one on-street spot that's usually available. 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 1940s cottage is part of the historic Camp Rose neighborhood, which means you'll have access to the semi-private Camp Rose river beach — a special perk only for residents! The home stays naturally cool thanks to cross-ventilation from its hillside perch, though air conditioning is available for warmer days. The vintage red and cream checkerboard flooring in the kitchen and laundry area is original to the home's 1940s character. The primary renter must be 21 or older. Your hot tub is private to your unit only, perfect for stargazing on clear mountain nights. The property is subdivided into two units; you'll have the lower unit with complete privacy and your own entrance. Those distinctive wall sconces and vintage details throughout are part of what makes this cottage so special — a true slice of old Healdsburg charm with modern comforts.

Healdsburg Fitch Mountain Hot Tub Cottage

Healdsburg, California, United States

Bed

Bath

Sleeps

$611.12

Summary:brbrAn 1895 Victorian turret door opens to wine country magic at this Magnolia Ranch cottage. Sip morning coffee on the gingerbread-trimmed porch as vineyard rows stretch to distant mountains. This colorful 2-bedroom retreat sleeps 4 amid crown molding and original hardwood floors. Just 1.3 miles from Healdsburg Plaza's tasting rooms and SingleThread. Set on a working vineyard, you'll enjoy the authentic Alexander Valley wine country experience.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.brbrbrbrTwo distinct sitting areas trade off — the main living room circles a painted-brick fireplace on Oriental rugs; a second room sets a tufted leather armchair beside its own brick fireplace. Crown molding, original hardwood floors, and built-in bookshelves tie the 1895 Victorian together. The modernized kitchen anchors with marble counters, a center island, a farmhouse sink, and a brand-new induction/convection oven — wine country cooking, period setting.brbrbrbrOUTDOOR LIVINGbrbrTwo furnished patios offer alfresco dining and relaxation against a backdrop of mountain and valley vistas. Fire up the gas grill for vineyard-view barbecues or spread a blanket beneath the grand walnut tree — this is wine country living at its most gracious.brbrbrbrSLEEPING ARRANGEMENTSbrbrThe queen bedroom is painted in warm terracotta tones with a white upholstered headboard and bay window nook. The king bedroom offers restful sleep amid period details and hardwood floors. Both rooms stay cool with central air conditioning. Two full bathrooms serve the home — one with white cabinetry, tan countertops, and a walk-in shower with gray tile; the second showcasing yellow walls, a pedestal sink, and white subway tile tub/shower combo. Total capacity: 4 guests.brbrbrbrPROPERTY AMENITIESbrbr-- Central air conditioningbrbr-- Full kitchen with new induction/convection ovenbrbr-- Washer and dryer in separate laundry roombrbr-- Gas grillbrbr-- Smart TVbrbr-- Parking for 2 vehiclesbrbrbrbrGuest Access:brbrStep onto the period porch of an authentic Victorian — octagonal turret, gingerbread trim — and look out over the surrounding vineyards. The whole farmhouse is yours, with outdoor dining and mountain, valley, and garden views from the windows. Punch in the keypad code on arrival; two smaller cars fit on the gravel pad, plus extra parking just before the house.brbrbrbrThe Neighborhood:brbrYour Victorian cottage sits in the heart of Healdsburg wine country, where three renowned wine regions converge. Just 1.3 miles away, the historic Healdsburg Plaza anchors downtown with its ring of tasting rooms, galleries, and farm-to-table restaurants. Stroll to nearby Tongue Dancer Wines (0.4 mi) or Arnot-Roberts (0.8 mi) for intimate tastings. When hunger strikes, Healdsburger (0.9 mi) serves gourmet burgers while The Parish Café (1.1 mi) offers California comfort food. For groceries, Lola's Market is just 0.9 miles away, with Safeway (1.2 mi) for larger hauls. Outdoor enthusiasts love Healdsburg Veterans Memorial Beach (1.0 mi) for summer swimming and Railroad Park (1.0 mi) for picnics. The Plaza hosts Saturday farmers' markets and summer concerts, while Michelin-starred SingleThread and casual Bravas tapas bar showcase the town's culinary range.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. Park in your private gravel spaces — two spots for smaller cars in front of the garage, with overflow parking near the house entrance. 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 1895 Victorian cottage offers authentic wine country charm with some delightful quirks. The decorative fireplace adds period character but isn't operational for guest use. While the home lacks air conditioning common in newer builds, you'll find it stays naturally cool thanks to well-insulated walls that keep the interior cool. The separate laundry room with mint green paneling and vineyard views makes longer stays a breeze. The property's owners do not live on-site. The home's well-insulated walls keep it naturally cool during hot summer days. The cottage requires guests be 25 or older. Keep an eye out for local wildlife that occasionally wanders through this working vineyard property. For the best experience, book dinner reservations well in advance, especially at SingleThread (weeks ahead) or popular spots like Valette and Bravas.

Healdsburg Victorian Cottage on Vineyard Estate

Healdsburg, California, United States

Bed

Bath

Sleeps

$868

Summary:brbrWake to vineyard rows stretching outside your window while morning light filters through the farmhouse. This playful 3-bedroom retreat brings color and fun to wine country — ping pong in the converted barn, bocce ball on the lawn, sunset dinners on the covered deck. Room for 6 with a fully equipped kitchen perfect for farmers' market finds. Just 2 miles from Healdsburg Plaza and minutes from Aperture Cellars. Your wine country escape comes with all the games — and all the views.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.brbrbrbrBoard games sit at hand around the wood-burning fireplace in the main family room; a second living area sets orange leather sofas beneath a painted-brick fireplace and exposed beams. A retro-style fridge and ample counter open the kitchen for prepping Healdsburg farmers' market hauls, flowing into dining inside and out on the covered deck. Out back, the converted barn is the wildcard — exposed trusses soar above a ping-pong table and built-in bookshelves, with a roll-up garage door that erases the line between indoors and out.brbrbrbrOUTDOOR LIVINGbrbrStep outside to discover multiple entertainment zones. The covered deck offers outdoor dining beneath bright orange metal chairs on a colorful striped rug. Challenge your group to bocce ball on the regulation court with its sandy surface and wooden rails. The converted barn steals the show — exposed ceiling beams and trusses soar above a blue ping-pong table, an orange sofa, and built-in bookshelves, with a roll-up garage door that opens to blur the line between indoors and out.brbrbrbrSLEEPING ARRANGEMENTSbrbrThree bedrooms sleep up to six guests. The primary bedroom offers a king bed with views overlooking the property. The second bedroom features a queen bed with white bedding. The third bedroom provides two twin beds with yellow accent pillows and large windows framing vineyard views.brbrbrbrPROPERTY AMENITIESbrbr-- Wood-burning fireplacebrbr-- Full kitchen with dishwasherbrbr-- Gas grillbrbr-- Ping-pong table in game barnbrbr-- Bocce ball courtbrbr-- EV charger (Tesla and CCS1 plugs)brbrbrbrGuest Access:brbrRoll up the barn door of the converted game room and let indoor-outdoor flow take over — ping-pong, exposed beams, vineyard views right outside. You've got the whole farmhouse, with a wood-burning fireplace, BBQ, outdoor dining, and an enclosed yard. Punch in the keypad code on arrival; free parking for up to five cars, with an EV charger (Tesla and CCS1 plugs) free for guest use.brbrbrbrThe Neighborhood:brbrYour farmhouse sits in the heart of Healdsburg wine country, surrounded by working vineyards just 2 miles from the historic Plaza. Walk next door (0.2 mi) to taste at Aperture Cellars, or explore nearby Christopher Creek Winery (0.5 mi) and Merriam Vineyards (0.6 mi). The famous Foppiano Vineyards, family-owned since 1896, is just 0.6 miles away. When hunger strikes, Healdsburger serves gourmet burgers 1.8 miles away, while TISZA BISTRO (2.1 mi) offers European comfort food with schnitzel and spätzle. The charming Healdsburg Plaza (2.3 mi) anchors downtown with tasting rooms, galleries, and the Saturday farmers' market. For outdoor fun, Healdsburg Veterans Memorial Beach on the Russian River is just 1.5 miles for summer swimming and kayaking. Stock up on provisions at Estrella's Market & Taqueria (1.8 mi) or grab morning coffee at Ana's Cafe & Espresso (1.8 mi).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. You'll find ample free parking for up to 5 vehicles on the property, including EV charging. 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:brbrThe home stays naturally cool thanks to cross-ventilation and shade trees, with air conditioning available for warmer days. Internet runs at 32 mb/s download speed, perfect for streaming. The primary renter must be 25 or older. Take advantage of the free EV charger — it works with both Tesla and CCS1 plugs. The converted barn game room is a special treat — roll up the garage door for indoor-outdoor ping pong matches. Don't miss sunset from the picnic tables by the bocce court. For the best farmers' market experience, visit Healdsburg Plaza on Saturday mornings starting in April. The property's one-acre setting means you'll enjoy privacy and quiet, with only the occasional tractor passing by during harvest season.

Healdsburg Vineyard Farmhouse with Game Barn

Healdsburg, California, United States

3

Bed

Bath

Sleeps

$1028.05

Summary:brbrSoak in the Rooster-side hot tub as the Russian River Valley fades into sunset; the next morning, gather your crew on the Dragon-side rooftop deck for coffee in the treetops. Two 1940s Camp Rose cottages share this Fitch Mountain hillside, knit together as one whole-cabin stay — 7 bedrooms, two stone fireplaces, two kitchens, sleeps 16. Half a mile to the river beach; two miles to Healdsburg Plaza, SingleThread, and Valette.brbrbrbrThe Space:brbrSpend mornings on the deck as light catches the willows along the river, afternoons paddling the Russian River or sipping at Aperture Cellars and Stuhlmuller, and evenings on the patio with a Healdsburg Plaza bottle and dinner from the grill.brbrbrbrTHE DRAGON SIDE (upstairs, sleeps 12)brbrAn open living room gathers around a stone fireplace between white built-ins, a light grey sectional and a black leather lounge angled toward the valley view. The galley kitchen keeps the 1940s Camp Rose period alive — yellow-and-grey checkerboard floor, white cabinets, a gas range, and a windowed breakfast nook for two. A separate dining room seats six at a light-wood table beneath panoramic hillside views. Five bedrooms sleep twelve: a master with a king and calming blue-green walls, a queen bedroom with TV, a kids' room with twin beds and a trundle, a play-room bedroom with red slide and daybed, and a fifth with a double plus two twins.brbrbrbrTHE ROOSTER SIDE (lower, sleeps 4)brbrA floor-to-ceiling natural-stone fireplace anchors the living room, a grey sectional and two navy cane-back chairs gathered under wall sconces. The vintage kitchen continues the period look — white cabinetry, dark hardware, wood-tone counters, and a red-and-cream checkerboard floor. Two bedrooms: a primary with a king and a twin trundle tucked beneath, plus a second bedroom with a twin. The deck out back wears a pergola throwing dappled shade over a private hot tub.brbrbrbrOUTDOOR LIVING (SHARED)brbrRussian River Valley views from nearly every window. The Dragon-side rooftop deck catches sunsets over the valley. The Rooster-side hot tub deck sits beneath a pergola. The backyard runs a playground with swing set, gymnastics rings, and ping-pong table; a BBQ grill, hammock, and mature trees finish the hillside.brbrbrbrSLEEPING ARRANGEMENTSbrbrSeven bedrooms across both sides sleep sixteen — see the per-side detail above. Each side has its own bath; book Dragon and Rooster together for a 16-person reunion, or one side alone for a smaller stay.brbrbrbrPROPERTY AMENITIESbrbr-- Central air conditioning throughoutbrbr-- Two full kitchens (gas range and dishwasher on the Dragon side)brbr-- Two stone fireplacesbrbr-- Private hot tub on the Rooster-side deckbrbr-- Washer and dryer in each unitbrbr-- Two designated driveway spots (one per side)brbrbrbrGuest Access:brbrYou've got the whole Fitch Mountain Cabin when you book — the Dragon side and the Rooster side, both cottages, the entire property, no other guest party sharing the lot. Grab the keys from the lockbox at each door: the Dragon side opens to the living room with the stone fireplace, the Rooster side leads out to the deck and the private hot tub. Kick around the swing set, fire up the BBQ grill, take in the Russian River Valley view from the rooftop deck. Two designated driveway spots, one per cottage, plus one usually-open on-street spot — neighborhood parking is tight.brbrbrbrThe Neighborhood:brbrYou're perched on Fitch Mountain in the historic Camp Rose neighborhood, half a mile downhill to the semi-private Camp Rose river beach (residents only) and Del Rio Woods Regional Park for Russian River swimming. The Fitch Mountain Park trailhead sits 0.9 miles up the road for hillside hiking with valley views, and Villa Chanticleer Dog Park is the same distance. Downtown Healdsburg's Plaza lies two miles down the hill — SingleThread Farm Restaurant (three Michelin stars) and Bravas Bar de Tapas at one end, Valette at the other, Saturday farmers' markets and summer concerts on the square. Stock up at Shelton's Natural Foods Market or grab sandwiches at Journeyman Meat Co. on the way home (both 1.9–2.0 miles). Wine tasting starts close: Hirsch Vineyards Tasting Room is 1.6 miles, Sapphire Hill and Truett Hurst sit 1.7 miles out, and the actual vineyards of Dry Creek, Alexander Valley, and Russian River Valley fan out within a 15-minute drive.brbrbrbrGetting Around:brbrHealdsburg is about 75 minutes from San Francisco via US-101 North — a straight, scenic drive into the heart of Sonoma County. You've got two designated parking spots in the driveway (one per cottage), plus one on-street spot that's usually open; neighborhood parking is regulated, so leave a fourth car at the Plaza (two miles away) if your group rolls deep. A car is the easiest way to take in the three valleys that meet here — Dry Creek, Alexander, and Russian River — but for tasting days, plan a designated driver or book a rideshare ahead.brbrbrbrOther Things to Note:brbrWhen you book the whole Fitch Mountain Cabin, both cottages and the full property are yours — no second guest party on the lot. The two cottages are part of the original 1940s Camp Rose neighborhood, which means you've got access to the semi-private Camp Rose river beach, a perk reserved for residents. The home stays naturally cool thanks to central air and the hillside breeze, but expect charming vintage quirks: a cozy galley kitchen on the Dragon side, original built-ins and wall sconces on the Rooster side, those distinctive checkerboard floors in both. The primary renter must be 21 or older. The hot tub on the Rooster-side deck is yours — perfect for stargazing on clear mountain nights. Watch little ones on the narrow Dragon-side deck and the rooftop, both with sweeping but unfenced drops to the valley. Those Russian River Valley views from nearly every window never get old, especially at sunset.

Fitch Mountain Cabin - Healdsburg Hillside Retreat with Hot Tub and Fireplace

Healdsburg, California, United States

7

Bed

Bath

16

Sleeps

$261.9

Summary:brbrThe Russian River Valley unfolds below your hillside perch at this cottage with panoramic views. Gather your crew of 12 in colorful, mid-century inspired spaces while kids play on the private swing set. Just 0.5 miles to Del Rio Woods Beach for river swimming and 1.9 miles to Healdsburg Plaza's tasting rooms and SingleThread. The rooftop deck puts you among the treetops — perfect for sunset toasts over the valley.brbrbrbrThe Space:brbrSpend mornings on the deck as light catches the willows along the river, afternoons paddling the Russian River or sipping at Aperture Cellars and Stuhlmuller, and evenings on the patio with a Healdsburg Plaza bottle and dinner from the grill.brbrbrbrA stone fireplace flanked by built-in shelving anchors the open living room, a sectional and leather lounge chair angled toward the valley. Exposed beams add cottage character overhead. The galley keeps the 1940s Camp Rose spirit alive with its yellow-and-grey checkerboard floor, a gas range, and a windowed breakfast nook for two. A separate dining room — orange accent wall, six-seat table — pulls the valley in through panoramic windows.brbrbrbrOUTDOOR LIVINGbrbrA narrow deck with white railings runs along the house, furnished with wooden lounge chairs sporting blue and white striped cushions, a red patio umbrella, and a geometric outdoor rug — your front-row seat to the valley panorama. The backyard is a playground paradise with a turquoise platform stage, red metal swing set with gymnastics rings and green swing, and turquoise metal chairs under mature trees. A ping-pong table rounds out the outdoor fun.brbrbrbrSLEEPING ARRANGEMENTSbrbrFive bedrooms sleep up to twelve guests. The master features a king bed and calming blue-green walls. A queen bedroom includes a wall-mounted TV and patterned area rug. One kids' room offers twin beds with a trundle and an orange accent wall. Another bedroom serves as a children's play space with a red slide, desk area, and daybed. The fifth bedroom provides a double bed plus two twins, one with a trundle.brbrbrbrPROPERTY AMENITIESbrbr-- Central air conditioningbrbr-- Full kitchen with gas range and dishwasherbrbr-- Stone fireplacebrbr-- Gas grillbrbr-- Ping-pong tablebrbr-- Deck and balconybrbrbrbrGuest Access:brbrStep out to a hillside deck where panoramic valley and mountain views fan out, then cook on retro-modern checkerboard kitchen floors back inside. You've got the whole cottage, with a stone fireplace, a ping-pong table, outdoor dining, and a family-friendly play yard. Grab the key from the lockbox; one designated drive spot, plus one usually-open on-street spot — neighborhood parking is tight.brbrbrbrThe Neighborhood:brbrYour Fitch Mountain perch puts you 0.5 miles from Del Rio Woods Regional Park with its Russian River swimming access and 0.9 miles from the Fitch Mountain Park trailhead for hillside hikes. Downtown Healdsburg's Plaza lies just 2.0 miles away, where you'll find SingleThread Farm (three Michelin stars), Bravas Bar de Tapas (1,731 reviews), and Valette for special occasions. Closer to home, grab provisions at Shelton's Natural Foods Market (1.9 miles) or coffee at the charming são francisco cafe (0.9 miles). Wine tasting starts 1.6 miles away at Hirsch Vineyards Tasting Room, Sapphire Hill Winery (1.7 miles), or Truett Hurst Winery (1.7 miles). For family fun, Villa Chanticleer Dog Park sits 0.9 miles away, and Healdsburg Veterans Memorial Beach offers summer swimming 1.6 miles down the road. The historic Healdsburg Plaza (2.0 miles) hosts Saturday farmers' markets and summer concerts.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. Park one vehicle in the driveway spot and another on the street (when available) — parking is strictly regulated in this neighborhood with only these two spots. 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:brbrThe home stays naturally cool thanks to central air conditioning — a real treat during Healdsburg's warm summers. As one of the original 1940s Camp Rose cottages, you might notice charming quirks like the galley kitchen's cozy proportions or the home's vintage built-ins. The primary renter must be 21 or older. Your cottage is part of a subdivided property with another unit — a second guest party may be present on the property at the same time. You'll have complete privacy in your space. Parking is shared: the upstairs unit parks in the spot closest to the front yard, and the downstairs unit parks in the spot next to the lemon tree. The narrow deck offers spectacular views but keep an eye on little ones. Those valley vistas from nearly every window never get old — especially at sunset from the rooftop deck.

Healdsburg Fitch Mountain Cottage with River Valley Views

Healdsburg, California, United States

Bed

Bath

Sleeps

$333.33

This gorgeous 1800 sq foot cottage was completely renovated and has an open floor plan, with an indoor-outdoor flow. It features 3 bedrooms, 2.5 bathrooms, and a huge kitchen (including stainless appliances, two big sinks, a wine fridge and *plenty* of cooking tools).brbrThere's a covered front porch perfect to enjoy breakfast or coffee in the morning, and a large backyard with a flat grassy area as well as a big patio with sofas for lounging, a dining area, a BBQ and a gas fire pit (s'mores anyone ). The yard also includes several fruit trees including lemon, lime, orange, apple and pomegranate. brbrThe house is on a quiet street with almost no through traffic (it's rare in Healdsburg to avoid the street noise!). There is plenty of on-street parking, and a driveway if you prefer. Downtown Healdsburg is a short 10 minute walk away, or an even shorter bike ride. Multiple parks are within a few minutes walk as well. brbrTwo adult bikes are available, as well as three kids scooters (Micro Kickboard brand), an Uppababy stroller, a pack and play, a full size crib (or it can be a toddler bed), and many Montessori-type toys and books (wooden blocks, etc).brbrOther notes: For the security of our guests and the safety of our home, we have a Ring doorbell camera located at the front door. It records audio and visual when there is any activity outside the door (faces front porch only - not inside). It is turned on and active.

Gorgeous Healdsburg house in town. Great location, fire pit, yard, huge kitchen!

Healdsburg, California, United States

Bed

Bath

Sleeps

$3376.3

Panorama Estate is more than a villa, it’s an escape. The estate’s spacious 5,000 square feet main house has 4 ensuite bedrooms, designer furnishings and a newly updated kitchen. The barn building complex has two additional bedroom suites. Nestled on 63 acres, the estate features an array of exclusive amenities: a tennis court with views, mini soccer field, play structure, fitness room, two miles of private hiking trails and a sparkling pool and hot tub. From sunrise to moonrise, the panoramic views over the rolling hills and vineyards are simply unforgettable.brbrPanorama House Interior DetailsbrEnter the grand light filled entrance hall and be prepared to be captivated. The main level features a new large gourmet kitchen with high-end appliances, a massive marble island with seating for six, and direct access to an outdoor terrace.brbrThe kitchen opens directly to the heart of the home, the great room, with floor-to-ceiling glass doors that open to the terrace and breathtaking views over Dry Creek Valley and to Mount St. Helena. An L-shaped sofa invites you to relax with friends and family while the dining area comfortably seats ten people.brbrAlso, on the Main Level you will find a formal living room with fireplaces and terrace access, a comfortable media room with an oversized flat screen TV, a large office, and an elegant powder room. and a wing with a mudroom with washer and dryer, a full bathroom and a small room with a twin bed for a child, teenager or nanny.brbrA wide stone staircase leads from the entrance hall to the bedrooms. The primary suite has a king bed, ensuite bathroom, and balcony. There is another king bedroom with balcony, and two queen bedrooms, each with an ensuite bathroom. On the first floor is an additional sleeping room with a twin bed and new bathroom in the same hall. brbrExterior DetailsbrOne approaches Panorama Estate via a gate entrance and long driveway that winds past the tennis court up to the main house parking area including the detached 2 car garage.brbrThe wide stone terrace stretches across the home with commanding views, a built in BBQ, outdoor dining and a shaded sitting area. Stone stairs lead to a relaxing in ground hot-tub and the pool area complete with umbrellas, and a shaded pergola with outdoor kitchen and seating. In the vicinity of the main house, you will find seasonal vegetable and flower beds, and multiple fruit trees. Near the main house is a mini soccer field, play structure and access to private hiking trails which meander through peaceful wooded areas provide endless activities. Also on the property is a tennis court with stunning views.brbrThe barn building, which is a short walk from the main house, features a spacious playroom downstairs with a large TV, ping pong table and a separate fitness room. On the second floor are two additional ensuite queen sleeping rooms, both with a sitting area and one with a kitchen.brbrHouse RulesbrPanorama Estate is subject to local regulations governing vacation rental properties. Under local law, events, parties and outdoor amplified music are not allowed. Overnight and daytime occupancy is limited to 12 guests, and rental guests must observe quiet hours between 9:00pm and 9:00 am. No pets allowed. The pool is heated Memorial Day through September. Note that the pool is not fenced or covered. Please contact your BeautifulPlaces representative with any questions about the features, amenities or policies for this house.brbrbrSonoma County TOT#4535N. Sonoma Vacation Rental Permit # TVR-22-0159, license LIC24-1204.

Panorama Estate - Classic Wine Country Villa in Healdsburg

Healdsburg, California, United States

Bed

Bath

Sleeps

$1309.68

★ PROPERTY HIGHLIGHTS ★brbr✔ Poo/Spa: Dip in the pool, relax in the hot tub, and enjoy mountain views!br✔ Space: Relish the solitude of this large 1,840 ft2 home.br✔ EV Charger: Tesla charger—ideal for keeping your vehicle powered up!br✔Views: Enjoy spectacular views of the surrounding mountains.br✔ BBQ: Dine al fresco while eating a delicious BBQ lunch.brbr★ OVERVIEW ★brSet on 3 acres in Sonoma wine country, Chatthaveli Healdsburg offers a serene retreat just minutes from downtown Healdsburg and top wineries. Surrounded by rolling hills, farms and vineyards, the home is just a 7 minute drive from Healdsburg Plaza, where you can explore upscale restaurants, tasting rooms, and local events.brbr★ LIVING AREAS ★brRelax in the inviting living areas, furnished with stylish seating and adorned with modern decor. Unwind after a day of exploration and let the designer touches envelop you.br✔ Stylish Seating: Sink into plush seats and indulge in absolute comfort.br✔ Modern Decor: Enjoy the curated ambiance created by the contemporary furnishings.brbr★ KITCHEN & DINING ROOM★brThe gorgeous open kitchen is a culinary haven, perfect for creating memorable meals. Gather around the dining table and experience the pleasure of dining in style.brbr✔ Designer Kitchen: Discover a well-appointed kitchen with an island that combines elegance with functionality.br✔ Kitchen Amenities: Coffee maker (drip coffee maker & Nespresso), basic cooking essentials (seasonings, condiments, oil, vinegar, organic sugar, coffee, tea, etc.), microwave, full-sized fridge, range, oven, dishwasher, rice maker, toaster and blender.br✔ Dining Area: Share delicious meals and create lasting memories around the chic dining table with seating for 8.brbr★ BEDROOMS ★brRetreat to the cozy bedrooms, where comfort and luxury await. Experience a restful slumber amidst the softness of Egyptian cotton sheets.brbr✔ Luxurious Beds: Drift into dreamland on our premium beds, adorned with Egyptian cotton sheets.br✔ Serene Ambiance: Find solace and tranquility in the tastefully designed bedrooms.br✔ Primary Bedroom: King bedbr✔ Bedroom 2: Queen bedbr✔ Bedroom 3: Queen bed and 1 double bedbr✔ Bedroom 4: Double bed and 2 single bedsbrbr★ INDOOR AMENITIES ★br✔ Smart TV: Enjoy your favorite shows and movies on the smart TV.br✔ Air conditioning/Heating: A central heating and cooling system is installed throughout the house.br✔ Workspace: Perfect for digital nomads, helping you stay productive even while on vacation.brbrbr★ OUTDOOR AMENITIES ★brEnjoy outdoor living with a spacious backyard and separate patio, ideal for entertaining or simply unwinding as you take in the peaceful surroundings and beautiful sunsets.brbr✔ BBQ grill (gas): For grilling up those burgers, hot dogs, chicken, and vegetables for a fun al fresco lunch on the patio.br✔ Deck/Patio: Lots of comfortable outdoor seating as well as an outdoor dining area for everyone to enjoy.br✔ Hot tub: This sunken hot tub can be used all year round.br✔ Pool: Relax and unwind by your private pool with cozy chaise lounges! Pool heating available for a fee.br✔ Parking: There is free parking for up to 3 cars.

Wine Country Gem | Pool | Hot tub | BBQ

Healdsburg, California, United States

Bed

Bath

Sleeps

$991.76

Summary:brbrSet in the quiet countryside of Sonoma, this modern rustic home is the ultimate wine country escape! Offering bright free-flowing spaces, large outdoor living space, and overlooks an exquisite 36-foot 4’ deep lap pool with breathtaking views of the Alexander Vineyards beyond.brbrbrbrThe Space:brbrNewly remodeled, this modern rustic home brings the outside in with floor-to-ceiling windows, sliding french doors which lead out to a vast deck and outdoor area. Inside hardwood floors throughout and open concept living spaces create a luxury yet organic ambiance. This Sonoma Residence hosts an expansive fully-equipped kitchen perfect for cooking and gathering, and bright spacious living. Upstairs features the master and an additional bedroom, each featuring en-suite bathrooms.brbrbrbrThe Neighborhood:brbrMinutes from award-winning restaurants and shopping in downtown Healdsburg and steps away from world-renowned tasting rooms and vineyards, this residence is celebrated for its ideal location. The unique architecture offers a bright vast open space ideal for gatherings, cooking and relaxing.brbrbrbrOther Things to Note:brbrPrivate 36-foot 4' deep pool and vast outdoor area for lounging, and outdoor dining. Pool heating is available upon request. Note that it must be requested 24h hours in advance prior to check-in.brbrNewly remodeled home featuring all new appliances and technology.brbrMinutes from award-winning restaurants and shopping in downtown Healdsburg and steps away from world-renowned tasting rooms and vineyards.brbrPrivate heated outdoor showerbrbrSurround-sound indoor and outdoor speaker system.brbrPrivate parkingbrbrThis property is equipped with HVAC in all rooms.brbrbrbrVineyard ViewbrbrbrbrMinutes to Airport - Charles M. Schulz–Sonoma County Airport, CA- 21 min. drive to residence. Or, San Francisco International Airport, CA- 2hrs.brbrbrbrAccidental Damage Protection: A non-refundable accidental damage protection plan is included in the price of your reservation. Under this plan, you will not be held responsible to pay for accidental damage or loss to the property resulting from you or the guests in your party up to $10,000. This plan does not cover intentional acts of a guest, gross negligence, or willful and wanton conduct. This plan is only available for stays less than 30 nights.

Modern Sonoma Home w Private Pool & Vineyard Views

Healdsburg, California, United States

Bed

Bath

Sleeps

$847.98

Summary:brbrHot Tub is in! 2 blocks from the Plaza, this 1880s cottage blends vintage charm with modern comfort. Walk to tasting rooms, shops & top dining, plus enjoy complimentary wine tasting at our favorite local wineries!brbrbrbrThe Space:brbr**Hot Tub is in!**brbrbrbrOur 1880s cottage has been part of Healdsburg’s story for over a century—now it’s ready to be part of yours. Just two blocks from the Plaza, this dog-friendly, standalone retreat blends vintage charm with thoughtful modern updates, including Wi-Fi, air conditioning, a dedicated workspace, and a private entrance.brbrbrbrNow featuring a **brand-new hot tub** and an **added full bathroom in the downstairs bedroom—creating a true en suite**, the home offers even more comfort and privacy for couples, friends, or families traveling together.brbrbrbrWalk to world-class tasting rooms, restaurants, and boutiques, then return to a cozy, character-filled hideaway where time slows and Wine Country living feels effortless.brbrbrbrThere’s something special about staying here—the creak of original floors, soft morning light in the sunroom, and the feeling of having your own private retreat in the heart of town.brbrbrbr---brbrbrbr### What You’ll Lovebrbrbrbr• Comfortable living room for unwinding after a day of wine tastingbrbr• Kitchen with copper countertops, drip coffee maker & Cuisinart K-Cup brewerbrbr• Two queen bedrooms (one upstairs, one downstairs), **both with easy access to full bathrooms—including a newly added en suite downstairs**brbr• Bright sunroom—perfect for morning coffee, reading, or remote workbrbr• Dedicated workspace with reliable Wi-Fibrbr• Two full bathrooms for added convenience and privacybrbr• Laundry closet for longer staysbrbr• Air conditioning for warm Wine Country daysbrbrbrbr---brbrbrbr### Outdoor Spacesbrbrbrbr• Covered front porch with rocking chairsbrbr• Private garden and backyard with gas grillbrbr• **Brand-new hot tub—perfect for relaxing under the stars (heating included)**brbr• Garage parking plus ample free street parkingbrbrbrbr---brbrbrbr**Dog-Friendly** – One well-behaved pup welcome (pet fee applies)brbrbrbr---brbrbrbr### Hospitality You Can Count OnbrbrbrbrGuests love the comfort and charm of our home, but it’s the thoughtful hospitality that keeps them coming back. We’re here to make your Wine Country getaway effortless, relaxing, and full of care.brbrbrbr---brbrbrbr### Local Winery Partnerships | Elevate Your Stay with Complimentary TastingsbrbrbrbrAs our guest, enjoy complimentary tastings at local favorites:brbrbrbr• Merriam Vineyards – Elegant, Bordeaux-style wines; $35 value per guest, complimentary for up to sixbrbr• Orsi Family Vineyards – Small-lot Italian varietals; $35 value per guest, complimentary for up to sixbrbr• Stonemason Cellars – Small lot wines all sourced locally from Sonoma County grapes. Enjoy their Nibbles & Wine tasting experience ($35 value per person)brbrbrbr*(Guest of record must be present for tastings.)*brbrbrbrAn unforgettable way to toast your Wine Country getaway—cheers to delicious moments ahead.brbrbrbr---brbrbrbr### Why Guests Love It Herebrbrbrbr• Walk everywhere—Healdsburg Plaza, tasting rooms, Valette, Costeaux French Bakery & morebrbr• Historic charm paired with thoughtful modern updatesbrbr• Private, standalone cottage with its own entrance and outdoor spacebrbr• The perfect balance of relaxation and access in Sonoma County wine countrybrbrbrbr---brbrbrbrFor your convenience, the home includes a portable crib, baby gate, and high chair.brbrbrbr**TOT# Banjoe Bungalow**brbrbrbrThe Neighborhood:brbrLocated in a quiet Residential Neighborhood just blocks from the Healdsburg Plaza.brbrbrbrGetting Around:brbrLyfts/Ubers are available although wait times can vary. Easily walkable to restaurants, bars, shops and tasting rooms.brbrbrbrOther Things to Note:brbrYou may also see this home listed as “Historic Plaza Gem - Wine Tastings Included” on some booking sites.

Healdsburg Plaza Gem-Hot Tub and Tastings Included

Healdsburg, California, United States

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Bath