Vacation Rentals By Owner In Healdsburg, CA

Luxury wine country estate on 9 private acres with stunning vineyard views, just 8 minutes to downtown Healdsburg Plaza. Olympic-size pool & spa. Large 3-bedroom main residence plus a separate and private 680sf guest cottage. Gourmet kitchen for group gatherings. Grand living room and fireplace. Multiple outdoor entertaining areas. World-class wineries and 140+ tasting rooms, Michelin-starred restaurants, Russian River & gorgeous hikes are minutes away. Your complete wine country escape.brbrMessage us on Social Media at Inspired in Sonoma for Inspiration and Tips.brbrWelcome to your wine country sanctuary—a luxury Healdsburg retreat where rolling vineyard views meet resort-style living on nine private acres. This is where your story begins: sunrise coffee overlooking endless grapevines, afternoons by the Olympic-size pool or in the game room, evenings gathered around the fireplace sharing the day`s wine-tasting adventures, and nights watching films in the movie room or lounging under star-filled Sonoma skies.brbrYour estate features a beautifully appointed main home plus an 680 square-foot private guest cottage with private deck and kitchenette, offering the perfect balance of togetherness and retreat for groups of friends, multi-generational families, couples traveling together, or anyone seeking the ultimate wine country experience.brbrYOUR WINE COUNTRY HOMEbrStep into the heart of the home—a stunning gourmet kitchen designed for culinary adventures and lazy morning gatherings. With expansive countertops, professional-grade appliances, and space for everyone to contribute to meal prep while sharing stories, this is where memories are made. The open flow connects seamlessly to the inviting living room, where a grand fireplace anchors the space and floor-to-ceiling windows frame captivating vineyard panoramas.brbrThe main residence offers thoughtfully designed bedrooms, each a peaceful sanctuary with views that remind you exactly where you are: the heart of California`s most celebrated wine region. Each master suite includes en suite bathroom + Jacuzzi tub. brbrYOUR PRIVATE WINE COUNTRY RESORTbrStep outside and discover your personal playground. The Olympic-size swimming pool sparkles in the Sonoma sunshine, perfect for morning laps or afternoon lounging, while the spa invites evening soaks while vineyard sunsets paint the sky gold and rose. Multiple outdoor living areas, from intimate conversation nooks to expansive entertaining spaces, ensure everyone finds their perfect spot.brbrNine acres of countryside provide the peace and privacy you seek. Yet you`re just eight minutes from downtown Healdsburg`s renowned Plaza, where Michelin-starred restaurants, boutique tasting rooms, artisan shops, and the vibrant farmers market await.brbrYOUR HEALDSBURG ADVENTUREbrThis isn`t just about where you stay—it`s about experiencing everything that makes Healdsburg extraordinary. Begin your mornings cycling through Alexander Valley`s vineyard-dotted roads or hiking Armstrong Preserve Redwood Forest. Spend afternoons exploring over 140 nearby wineries, from legendary estates to intimate family operations where winemakers pour their own creations. As evening approaches, secure reservations at celebrated restaurants like SingleThread or Valette, where farm-to-table cuisine perfectly complements the region`s exceptional wines. Healdsburg`s celebrated events unfold throughout the year: the legendary Wine & Food Experience in May, harvest crush festivities in fall, intimate winter jazz performances, the vibrant Farmers Market year-round. Whatever brings you to wine country, this estate serves as your luxurious home base for every adventure.brbrYOUR PERFECT GROUP GETAWAYbrThis is more than a vacation rental—it`s your gateway to the wine country lifestyle, where every detail has been considered and every moment invites you to slow down, savor, and celebrate. The vineyard views are calling. The private resort is ready. The adventure begins now.brbrBook your escape to wine country`s most coveted destination retreat with breathtaking vineyard views! brbr***Please note***brSwimming pool can be heated up to 83 degrees for a fee of $150 per day with a 3 day minimum.brIf you would like to have the pool heated, please contact Kharis at least two weeks in advance of your stay to ensure this can be accommodated brPool is 60x14.5 feet brbrWi-FibrWi-Fi at this property is radio wave Wi-Fi and has speeds between 35 mbps and 80mbps.brbrFull access to all areas with the exception of locked room in garage.brbrAvailable by Airbnb app or by personal phone as needed.brbrPrivate Country Property in the hills with Vineyard ViewsbrbrYou will need to drive your car here and wherever else you need to go. Uber and Lyft are available but can be unreliable.brbrThe views from the deck are amazing. Wine Country at its finest.

Wine Country Estate: Pool, Spa & Vineyard Views

Healdsburg, California, United States

Bed

Bath

Sleeps

$1856.3

You'll never want to leave this serene retreat with everything you need to relish in indoor/outdoor living. brbrJust 5-10 minutes from award winning wineries and only 15 mins from downtown Healdsburg.brbrThis spectacular two-story home is nestled on 25+ acres and offers privacy, relaxation, and beautiful views of the sprawling redwood forest. Sleeps 12 across three bedrooms and 3 bonus rooms with beds included. brbr1. Primary Suite (1st floor): King bed with en suite bathroom br2. Bonus Room (1st floor): Queen bed br3. Bedroom (2nd floor): Queen bed br4. Bedroom (2nd floor): Queen bed br5. Bonus Room (2nd floor): Queen bed with huge closet br6. Bonus Room (2nd floor): Twin beds brbrThe glass-doored entry leads directly into the living room open to the kitchen and dining area with a large island. To the right of the entry you'll find a bonus room with a queen bed, followed by the large primary suite with en suite bath, walk-in closet and huge windows to take in the beautiful views. Also on the main floor is a cozy TV room, full bath, half bath and laundry room.brbrThe kitchen was designed using premium appliances for the ultimate cooking and entertaining experience. You’ll enjoy a stocked pantry with all basic cooking equipment and pantry essentials. Guests can enjoy complimentary coffee from both espresso and coffee machines. brbrUp the open staircase and landing that overlooks the living room, you'll find two more bedrooms with queen beds and 2 additional bonus rooms - 1 with a queen bed and 1 with twin beds. There's also another full bath.brbrA Private and Peaceful Outdoor Experience: Step outside into your own 25+ acre private wine country paradise, designed for effortless indoor-outdoor living to create unforgettable moments:brbr- The expansive front porch overlooks the pool and hot tub, outdoor dining area and inviting gathering spaces. Soak in views of the sprawling redwood forest - this is the ideal spot to cool off by day or soak under the stars at night. br- The pool has a retractable cover for safety when not in use or when children are present. br- The back deck wraps around the house and also comes with a ping pong table.br- The side grass lawn is the perfect place for kids to play - with a large deck for adults to hang nearby.br- Playfully explore miles of private hiking trails, walking creekside, enjoying hidden nooks and quiet nature.brbrThis is the perfect place for family and friends to gather in a relaxing atmosphere of comfort, luxury and serenity. The home is just minutes from a number of the area’s award winning wineries such as Lambert Bridge, Dry Creek Vineyard, Passalacqua Winery, Quivira Vineyards and Aesthete Winery & Farm. Just a short drive (7 miles or 15 min) to the Healdsburg Plaza. Your stay won’t just be a vacation, it will be an unforgettable experience.

Private Oasis in Healdsburg: Pool, Spa & Views

Healdsburg, California, United States

Bed

Bath

Sleeps

$369.6

Wonderful river getaway in a cabin on North Fitch Mountain Rd. Lots of trees, views of the Russian River, and easy river access. River chairs, shading, and accessories provided to practically guarantee a perfect day of rest and relaxation after exploring the downtown or one of the beautiful local wineries. brbrBuilt into the hillside, a cozy 2 bedroom one bath get away to rest and relax. Well stocked kitchen (condiments and spices to help you execute your meals) with a table that sits 6 easily. Living room opens to a river facing deck with outdoor dining and relaxation options. brCabin is two levels built into the hillside. Lower level is is reserved for the owner's residence. Both levels have separate entrances and decks with views. brbrLiving area and bedrooms have air conditioners for those hot summer days. In addition for those brisk days, the living room has a gas fireplace to snuggle up in front of with a good book or your favorite show.

Cottage

Russian Riverside Cottage in Healdsburg

Healdsburg, California, United States

Bed

Bath

Sleeps

$5656.0

Summary:brbrUncover a hidden gem on 120 stunning acres, ideal for intimate weddings, celebrations, corporate retreats, board meetings, and family vacations, just minutes from downtown Healdsburg! With two luxurious villas for up to 12 guests, this resort-style sanctuary offers rejuvenation, connection, and warm hospitality. Enjoy organic meals from the garden, wellness activities, and outdoor adventures.brbrbrbrThe Space:brbrThe Best of Both WorldsbrbrbrbrOur two luxury villas offer an immersive stay in nature with comfort and style. Nestled between beautiful pastures and scenic hills, The Estate Villa is a four-bedroom, four-bath estate that combines the luxuries of a high-end resort with the privacy of home. The Barn Villa, a two-bedroom, two-bath modern barn, sits above a one-acre garden and is surrounded by hiking trails and towering Redwoods, blending barn house and tree house charm. brbrbrbrUnique Ranch Experience in Wine CountrybrbrbrbrTravel + Leisure, “50 Best Places to Stay.” The property is private and peaceful yet very conveniently located — only a 10-minute drive to the wonderful restaurants, wineries, and shops in downtown Healdsburg, California. Healdsburg is a top destination in Sonoma County’s wine country, named one of the best places to visit in 2021 by Condé Nast Traveler.brbrbrbrAccommodationsbrbrbrbrThe villas are a luxury oasis with all the comforts of home. Each of the six king bedrooms has a private bath, freshly ironed luxury Frette Italian Linens washed with the ranch's pure water, and premium Avocado organic mattresses. You can fully unwind in the primary bathroom’s freestanding tub or curl up by one of two wood-burning fireplaces. The library is filled with books and games for laid-back evenings by the fire. The home has an automated lighting system and audio/visual is connected throughout the house by Bose Soundtouch.brbrbrbrElevate Your WellnessbrbrbrbrEnjoy our state-of-the-art chef’s kitchens, stocked with farm-fresh produce, and a range of amenities including a 1,200-square-foot fitness center, a private lake, horse stables, an animal sanctuary, gardens, an outdoor glamping tent, a Japanese zen garden, an outdoor Balinese tub, and an outdoor chef’s kitchen with dining area. brbrbrbrYour Perfect ItinerarybrbrbrbrWe’re here to help you with all your celebration plans, from curated dining experiences to unforgettable activities, ensuring your stay is perfect. You may choose from a plethora of experiences right here on the ranch. From arranging Tesla transportation to curating experiences both on and off the ranch, we ensure every detail is handled with precision. Let us take care of the details so you can enjoy quality time with your friends and family! brbrbrbrOne-of-a-Kind Activities, Any Time of YearbrbrbrbrChoose from a plethora of activities right here on the ranch. During warmer months, take a dip in the pool (solar heated May - October) or paddle on our private lake.brbrbrbrFor cooler days, arrange for massages in the picturesque outdoor tent heated via wood burning fireplace, followed by a soak in the clawfoot bathtubs overlooking the breathtaking landscape and grazing wildlife.brbrGuests are also invited to spend time with our dear animal friends who live in the stables on property — goats, a sheep, a pony, and Scottish highland cows.brbrNewTree is a working farm and you are welcome to observe and participate in harvesting the vegetables, planting new seeds, and feeding the animals, as you wish.brbrbrbrBring Your Furry FriendsbrbrbrbrYour pets are always welcome during your stay, as are your horses. The stables are fully equipped to house horses and the property is magnificent for riding.brbrbrbrCulinary DelightsbrbrbrbrA culinary paradise, we have everything you need to create phenomenal meals. Gather freshly-laid eggs from the chicken coop and savor the incredible variety of delicious, organic vegetables grown on property. The newly renovated chef’s kitchen is complete with culinary tools and gourmet cookware, as well as a fully stocked pantry with flavorful spices, pasta, grains, and other dry ingredients. Or if you’d prefer to have someone else cook for you, our private chef crafts exquisite dishes from garden-fresh produce.brbrbrbrHealthy Environment, Healthy YoubrbrbrbrThe entire property is a toxin-free environment. Each indoor space is in an intentional sanctuary with air purifiers throughout and our team only utilizes non-toxic cleaning products to maintain pristine, healing spaces. Additionally, the water is tested regularly, the linens are laundered and ironed onsite, everything grown at the farm is bio-dynamic and all natural, and the skin care products are made from the best quality ingredients. Every aspect of our property, from the soil to the craftsmanship, is biodynamic, regenerative, and sustainable. This commitment allows you to know you’re being taken care of in every possible way.brbrbrbrJoin UsbrbrbrbrWhen you choose NewTree Ranch, you’re standing for something better than a crowded hotel with no real place for your group to privately gather. Instead, you’re immersing yourself in a life of laid-back luxury, where our team anticipates your every need before you even ask for it.brbrbrbrIf you’re ready to experience the breathtaking beauty and exquisite details of NewTree Ranch, we invite you to book your stay today.brbrbrbrbrbrHIGHLIGHTS: brbrbrbr- Personalized pre-trip planning brbr- A dedicated on-site team to manage every detail brbr- Curated ranch experiences brbr- Private chef option brbr- Stocked pantry with delicacies from the garden brbr- Spacious interiors to accommodate large groups with 6+ bedrooms and elevated outdoor spaces with pools, outdoor tubs and showers, and fire pits brbr- Animal sanctuary, horse stables, and guests’ pets welcome brbr- Solar-heated outdoor pool from May to October brbr- Access to indoor gym & fit trail brbr- Tesla transportation for 6 night bookingsbrbrbrbrAS SEEN ON..brbrbrbr• Travel + Leisure, “10 Family-friendly U.S. Ranches to Experience the Great Outdoors”brbrbrbr• Forbes Magazine, Northern California's NewTree Ranch is Redefining luxury.brbrbrbr• Haute Living, “NewTree Ranch: A Place for Revival, Restoration, and Renewal”brbrbrbr• Travel + Leisure, 50 Best Places to Stay.brbrbrbr• Departures, 10 Luxury Experiences for Eliminating Negativity.brbrbrbr• 7 X 7 Magazine, NewTree Ranch: Totally Private Digs Near Healdsburg.

Luxury Estate | Gatherings | 2 Villas Organic Farm

Healdsburg, California, United States

Bed

Bath

Sleeps

$272.45

Modern sophistication meets wine country charm in this Healdsburg townhome, nestled among beautiful redwoods. This light-filled home features floor-to-ceiling windows, bamboo hardwood floors, Viking appliances, and both indoor and outdoor fireplaces. A private deck offers the perfect spot to unwind or entertain.brbrThe loft-level second bedroom includes a new Thuma queen bed, full bathroom with shower and tub, closet, and linen storage. Note: this bedroom is located in the open loft area and is not fully private. Between the loft and the primary suite, you'll find a new Bosch washer and dryer. Upstairs carpeting is brand new and high-quality.brbrCommunity amenities include a pool, jacuzzi, pool house, and Viking BBQ. brbrJust a 10-minute walk to Healdsburg Plaza, residents enjoy easy access to local favorites like Little Saints, The Matheson, and Dry Creek Kitchen, as well as boutique shopping, wineries, and the lively summer music scene.brbrAvailable for a 1-month stay or longer-term lease (6 12 months). Rent includes HOA fees, Wi-Fi, Apple TV, PG&E, water, and garbage. No pets or smoking permitted. Convenient parking is available directly in front of the townhome.

Modern Townhome - Walking Distance to Healdsburg Plaza

Healdsburg, California, United States

Bed

Bath

Sleeps

$136.67

Located in Healdsburg, this condo is a dream. With 2 bedrooms featuring a queen and full bed, guests will feel right at home. The bathroom comes equipped with a hair dryer for added convenience. Enjoy the welcoming and soothing atmosphere of this wonderful property. Make your holiday one for the books with a stay at our place.

Condo

Tranquil 2-bedroom condo in Healdsburg with AC, WiFi

Healdsburg, California, United States

Bed

Bath

Sleeps

$472.66

Set on an Acre by Fitch Mountain Park and Open Space Preserve, Hilltop Vista Villa offers a quiet private setting, spectacular views of world class vineyards, private access to hiking trails and proximity to the Russian River beach.brbrThis inviting single level retreat has an open floor plan with lots of sunshine. The open kitchen features stainless steel appliances, custom cabinetry, and a granite topped island. The Master Suite includes a custom soaking tub.brbrAs Villa the only house in Preserve, it gives you your private access to the hiking trail and quietness all around. brbrThe house offers a contemporary open-floor design, high ceilings --13ft--and plenty of natural light. It includes a kitchen, dining area, living room, 2 bedrooms, and a backyard. brbrThe full kitchen includes granite counters, premium cabinets and modern appliances: range, oven, microwave, dishwasher and full refrigerator/freezer and filtered water. There's plenty of counter prep space and some wine racks. There's a bar-top/dining table with four stools. brbrThe living room features a fireplace. There's also a selection of books. This open space is ideal for working, entertaining and relaxation.brbrThe master bedroom presents a luxurious king bed with very comfortable, high quality, medium-firm mattress. it offers a dresser and a full length mirror. The second bedroom has a king bed with a medium/plush firmness mattress. Also, there is a desk, a dresser, and a closet with plenty of shelving. Both beds have soft and luxurious fitted 300-thread count Brooklinen's Egyptian cotton sheets.brbrThere are extra towels, pillows and blankets as well.brbrFor your convenience, there is a laundry room, and plenty off-street parking on our driveway.brbrOur fenced-in backyard offers an outdoor sitting. The back yard is ideal for barbecuing and for just hanging out. brbrNo smoking in the house.

Villa

Stay surrounded by Fitch Mountain Park and Open Space Preserve.

Healdsburg, California, United States

Bed

Bath

Sleeps

$1082.82

This stunning gated modern ranch house is nestled on one acre among the vineyards, and very well located at the north end of Healdsburg on Alexander Valley Road. Just remodeled, professionally decorated and furnished, this single story, 2000 sq. ft., 3 bedroom, 2.5 bath home sits under the shade of an impressive California Oak. This lovely home features abundant new decking with a large outdoor table for 10 and a beautiful new in-ground pool, 8-person Hot Springs spa and outdoor shower. Enjoy the attractive and comfortable outdoor furniture, bocce and basketball courts. A large covered outdoor entertainment area with grill and plenty of seating provides a wonderful entertaining space overlooking the pool and combines perfectly with the spacious entertainment room, especially when the two window walls are open, inviting the outside in!brbrThe hardwood-floored great room and professional-grade gourmet kitchen with Thermador 6 burner gas range, convection oven, natural stone countertops and large island with six stools for the backseat chefs. Adjacent to the kitchen is the dining area with a beautiful wood and metal dining table seating up to 8. brbrThe great room also includes the family room with a large sleeper sofa, enabling up to 8 overnight guests. A slate rock wall with a two-sided gas fireplace separates this area from the media /entertainment multi-purpose room with two window walls which open to the back covered porch. Amenities here include a large 70-inch flat screen Vizio TV with Soundbar, a large area rug and a large sectional sofa. brbrOff the living room is a dry bar with a wine fridge, convenient half bath and stacked Samsung washer/dryer set. To the right of the main entry and down the hallway are a queen bedroom with double closet, shared bath, king bedroom and master suite. brbrThe master bedroom has double mirror doored closets, a beautiful ceiling fan, queen platform bed, large window, and hardwood flooring with rugs. The Master's ensuite bath has a free-standing shower and single-sinked vanity.br*Heated pool may be available at an extra energy expenditure cost for entire stay, please remember to ask us (depend on availability).brbrCOME AND ENJOY RENDEZVOUS UNDER THE OAKS FOR A MEMORABLE ENCHANTING RETREAT IN ALEXANDER VALLEY, ONLY MINUTES FROM DOWNTOWN HEALDSBURG!

Rendezvous Under the Oaks-Pool & hot Spa

Healdsburg, California, United States

Bed

Bath

Sleeps

$130.0

Heartwood Guest House was born in 1880 and reimagined in 2020. As one of the original platted homes of Healdsburg, Heartwood House (and Guest House) are among the oldest buildings in the city—and you can experience a part of this heritage during a long-term stay (30+ days) in wine country!brbrHeartwood Guest House enjoys status as the closest guesthouse to the historic town plaza! This is in-town living at its finest and you will get to experience all that downtown living has to offer: the walkability, the restaurants, the tasting rooms, the shopping, the people, and more. brbrThis space is fully furnished and was refurbished in 2021. Throughout the space you'll notice original 11-ft high ceilings, vintage hardware, and curated artwork that add charm and honor the history of the house. brbrSpecial features of the space include:br- Private entrance through a gated patio space.br- One off-street parking space with additional on-street parking.br- Full-size kitchen in multipurpose room containing a 5-burner gas range + oven, compact refrigerator, microwave, and all cooking/serving utensils. br- Sitting area in multipurpose room with full-size sofa, desk, and Smart television with Hulu LiveTV. br- Bedroom containing a king size bed with Tuft & Needle mattress, electric fireplace, and large storage area.br- Bathroom with restored clawfoot soaking tub and shower enclosure, pedestal sink, and toto washlet toilet. br- In-unit laundry, Mitsubishi mini-split heating/air conditioning, high speed internet, tankless hot water heater. br- Dogs are welcome. brbrbr

Historic Guest House on Plaza Street

Healdsburg, California, United States

Bed

Bath

Sleeps

$422.61

Sunny, fun riverfront home in Healdsburg with direct access to Russian River and multiple indoor and outdoor areas to relax and enjoy your time. Great wine country location, less than 10 minutes to Healdsburg's Town Square, and less than 5 minutes to Ru's Farm, or Front Porch Farms. We have multiple decks, a screened porch, a private patio overlooking the river, and everything you need to enjoy them. TOT#3255NbrbrOur calendar is up to date and instant-booking is on.brbrThe spacebrbrMorning Dew is a quaint, 1920s home set under a beautiful old oak tree. In the main house, you'll find a well equipped eat-in kitchen and two separate living spaces where you can curl up by the wood stove with a good book, play cards, watch cable TV or use the WiFi. We have a well stocked kitchen, and provide coffee and tea.brbrThere are several options for sleeping, with a queen bed and a single bed in main house, and a second queen bed in the Love Shack (a rustic studio accessed by a separate entry below the main home). There is a full bath in the main house and a small bath with shower in the Love Shack. brbrThere are many outdoor spaces for relaxing and enjoying the sounds and views of the river. You'll find a shaded deck off the kitchen with a large table for outdoor dining, a small lounge area besides Love Shack, a screened porch part way down to the river, and a shaded platform that sits above the rocky beach.brbrWe have everything you need for a memorable river and wine weekend. Folding chairs, beach towels, and a cooler are available for lounging at the river. Winery maps and recommendations and a picnic basket help you make the most of your winery tour. You'll also find great hiking and road biking in the area, or can arrange a kayaking or canoe trip ending at nearby Memorial Beach.brbrGuest accessbrbrYou will have access to the entire property. We share the path down to the river with our neighbors, but the platform above the river is exclusively ours and there is plenty of room on the rocky beach for everyone to find their own space.brbrInteraction with guestsbrbrWhile we do not live onsite, we are available by phone or electronically for questions and advice. You can talk to me directly via the Ring doorbell anytime.brbrOther things to notebrbrPlease note there are many steep steps down to the river. Use of the stairs and river are at your own risk.brbrWe have a Ring video doorbell.brbrPlease note this is an old and quirky home situated in a rural area. While the oak tree brings lovely shade, it also regularly drops leaves and is home to lots of wildlife. While it varies by season, here are some of the creatures you may come across:brMost likely see - lizards, songbirds, jays, hawks, spiders, caterpillars. brProbably see - deer, ducks, fish, hummingbirds, vultures. brMight see - river otters, quail, snakes, field mice, skunks.brbrOur home is always professionally cleaned between visits, but if seeing a spider in the house could ruin your weekend, it may not be the best choice for you!brbrPlease message with any questions and we hope you enjoy your visit to Sonoma Wine Country!br

Morning Dew-A Riverfront Healdsburg Home

Healdsburg, California, United States

Bed

Bath

Sleeps

$1,072

This stunning, newly constructed modern home sits on a picturesque 10-acre property, complete with a thriving vineyard that provides a serene and secluded backdrop for your getaway.brbrAs you approach the property, you'll be immediately struck by the home's elegant and refined design with large picture windows and a seamless blend of indoor and outdoor living spaces. Step inside and you'll be greeted by a bright and airy great room, where the fully-equipped kitchen, dining area and comfortable living space flow together effortlessly.brbrAll three bedrooms offer a peaceful retreat with natural light and direct access to the home's beautifully appointed bathrooms. Gaze out the picture windows to take in the breathtaking vistas of the surrounding olive-dotted hills and endless sky.brbrJust a short drive from the charming town of Healdsburg, this property offers easy access to some of the world's best wineries and award-winning restaurants. Whether you are seeking a romantic getaway, a family vacation or a peaceful respite form the hustle and bustle, this exceptional Sonoma County retreat has everything you need and more. See more: https://youtu.be/9KMu6u2JJi0brThis property complies with Sonoma County TOT regulations.brbrMaximum stay 10 nights.brbrVRBO displays an all-in nightly average that includes cleaning and service fees — longer stays offer significantly better nightly value.

Wake Up in Your Own Private Vineyard - Healdsburg

Healdsburg, California, United States

Bed

Bath

Sleeps

$549.81

Summary:brbrTucked on a private one-acre property, Casa Campo sits five minutes from Healdsburg's legendary plaza—close enough to explore, quiet enough to exhale. A gas BBQ patio, deep soaking bathtub, ergonomic workspace, and fully stocked kitchen set the stage for long, unhurried days in Dry Creek wine country. Start mornings with pour-over coffee on the sun loungers, end evenings in the soaking tub with a local Zinfandel. Your California escape starts here.brbrbrbrThe Space:brbrStep into a peaceful, thoughtfully designed cottage that blends rustic warmth with modern touches. Casa Campo offers a comfortable, inviting layout that makes it easy to slow down, unwind, and fully enjoy your time in wine country.brbrbrbrAs you walk in, you’ll find a bright and cozy living area with ample seating, a 54 TV, curated books, and board games, perfect for quiet mornings, a glass of wine in the evening, or relaxing after a day of tastings around Healdsburg. The space also features a charming decorative fireplace that adds to the ambiance (for aesthetic purposes only and not available for guest use).brbrbrbrThe adjacent dining area flows seamlessly into a fully equipped kitchen, complete with an induction stove, oven, large refrigerator, microwave, coffee maker, wine glasses, and all the essentials you’ll need to prepare simple meals or enjoy a leisurely night in.brbrbrbrBoth bedrooms feature brand-new, comfortable beds, cozy linens, room-darkening shades, ample storage, extra pillows and blankets, and peaceful views of the surrounding trees.The bathrooms are stocked with toiletries and everyday essentials, including a relaxing bathtub for unwinding after a day of exploring wine country.brbrbrbrStep outside to a private backyard and patio, where you can sip your morning coffee, grill dinner on the gas BBQ, or relax on the outdoor seating and sun loungers surrounded by nature. With private parking for up to three vehicles, a single-level layout, strong Wi-Fi, an ergonomic workspace, air conditioning, heating, fans, and an in-unit washer/dryer, Casa Campo is set up for a comfortable and effortless stay from start to finish.brbrbrbrGuest Access:brbrGuests have full access to the entire home and the surrounding outdoor space throughout their stay.brbrbrbrThe Neighborhood:brbrCasa Campo is tucked into a nature-filled area just outside downtown Healdsburg. The setting feels quiet and private, while still being close to world-class wineries, charming tasting rooms, and some of Sonoma County’s best dining and shopping.brbrbrbrGetting Around:brbrA car is recommended for exploring the area, especially if you plan to visit wineries or spend time downtown. The neighborhood is calm and easy to navigate, and many popular destinations are just a short drive away.brbr- 5 minutes to Downtown Healdsburg Plazabrbr- 7 minutes to Memorial Beach on the Russian Riverbrbr- 13 minutes to Sonoma County Airportbrbr- Less than an hour to the Coastbrbr- 1 hour to San FranciscobrbrbrbrOther Things to Note:brbrThis home does not allow pets, with the exception of service animals. If you’re traveling with a service animal, please let us know before arrival and kindly clean up after them.brbrbrbrQuiet hours are from 9 PM to 7 AM, per local regulations.brbrThe driveway accommodates up to three vehicles, with free street parking also available.brbrbrbr To ensure a seamless check-in, all guests must complete a quick pre-check-in verification through our secure guest portal. A link will be sent after your booking is confirmed.brbr During the rainy season (typically October through March), outdoor furniture cushions may be stored to protect them from the elements, and outdoor seating may not be set up as pictured.brbrbrbrInteraction with Guests:brbrWe strive to achieve the perfect balance between providing our guests with the privacy they desire while remaining accessible for any questions or needs that may arise. We respect your space and ensure that your stay is as comfortable as possible. However, if you have any inquiries, require assistance, or simply want some local tips and recommendations, please don't hesitate to reach out to us. We're always more than happy to help make your stay a memorable and enjoyable experience.

Private Acre+BBQ Patio | 5min to Healdsburg Plaza

Healdsburg, California, United States

Bed

Bath

Sleeps

$1156.08

Summary:brbrSwim, soak, sip & savor—Healdsburg Homestead offers a pool, hot tub, and an exclusive complimentary tastings! Tucked in Dry Creek Valley, just minutes from downtown.brbrbrbrThe Space:brbrWelcome to Healdsburg Homestead!brbrIn the heart of Sonoma County’s Dry Creek Valley, this peaceful farmhouse sits along a quiet country road, surrounded by vineyards, gardens, and the gentle sound of a seasonal creek. Though it feels worlds away, you’re just 5 minutes from downtown Healdsburg’s tasting rooms, boutiques, and acclaimed restaurants.brbrWake up to birdsong and garden views, spend the day wine tasting or paddling on Lake Sonoma, then unwind in the hot tub beneath a sky full of stars. Whether celebrating, recharging, or simply soaking in the rhythm of wine country, every moment here is made to be memorable.brbrHighlights of Your Staybrbr• Prime Location – 5 minutes to Healdsburg, near world-class wineries like Dry Creek Vineyard, Ridge & Ferrari-Caranobrbr• Outdoor Living – Private pool with baja shelf, hot tub by the creek, gardens, bocce, and wide-open spacebrbr• Family & Pet-Friendly – Sandbox, toys, Pack ’n Play, and room for kids to roam (up to 2 dogs welcome, pet fee applies)brbr• Work & Relax – Vineyard-view workspace, fast Wi-Fi, and cozy living room with gas fireplacebrbr• Thoughtful Touches – Fully equipped kitchen, French press & drip coffee setup, and garden views throughoutbrbrbrbrWhile this home impresses with its comfort and setting, it’s the personal touches that make your stay memorable. From a warm welcome to attentive support throughout your visit, we ensure every detail is taken care of.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):brbr• 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!brbrbrbrSleeping Arrangementsbrbr– 3 Bedrooms, 2 Bathroomsbrbr– Pool ranges from 3.5’ to 6’ deepbrbr– Pack ’n Play providedbrbrbrbrHealdsburg Homestead welcomes you to one of the most beautiful corners of Northern California—perfect for romantic escapes, family trips, or weekends with friends.brbrbrbrTOT#: 4214N | Permit#: TVR20-0084 | LIC#: LIC23-0113brbrBooking is contingent upon acceptance of Property Manger's rental agreement (excludes Airbnb).brbrbrbrThe Neighborhood:brbrLocated in a quiet Residential Neighborhood.brbrbrbrGetting Around:brbrLyfts/Ubers are available although wait times can vary.brbrbrbrOther Things to Note:brbrYou may also see this home listed as “Homestead with Pool Hot Tub and Tastings Included” on some booking sites.

Healdsburg Homestead with Pool, Hot Tub and Tastings Included

Healdsburg, California, United States

Bed

Bath

Sleeps

$255.83

Unique rental opportunity — a beautiful, brand new home with an enormous open floor plan perfect for bringing family or a group together. A large wrap around porch, huge yard and plenty of off-street parking allow guests to settle in for several days without having to drive from place to place. You won’t want to leave this comfortably furnished home, but if you do it’s just 3 short blocks to the Plaza. Take a short walk or hop on one of the house bikes and you’re in the center of town, where you can experience award winning restaurants, galleries, 30+ wine tasting options and plenty of great shopping. Truly the best of both worlds — a modern farmhouse cozy setting just a few minutes from all the adventure of downtown Healdsburg. brbrThis brand new home has a spacious, fully equipped kitchen for entertaining with a peninsula bar and adjacent dining area. You can exit the dining area through French doors to the wrap around porch. Sonos surround sound speakers throughout the common rooms of the home and outside porch allow you to broadcast your favorite music while cooking, dining or hanging out. brbrA huge living room, with 20ft vaulted ceilings is the perfect place to gather a group or just lounge around enjoying the fireplace or TV. If you're looking for a more intimate space, make your way up to the loft and enjoy the mountain views from the cozy velvet couch.brbrBoth bedrooms upstairs are generously sized with vaulted ceilings and en suite bathrooms. The bedroom on the main level also offers plenty of space and includes seating and lots of storage. A full bathroom is located just across the hall from this bedroom.brbrWhile the indoors are beautifully decorated with many farmhouse details, the outdoors are also very inviting. Enjoy a glass of wine on the wrap around porch, or take a stroll downtown. There are two house cruiser bikes located in the garage with bike locks that are available to tenants. It's just a quick ride to the river, or seek out your favorite restaurant in town. There are so many options when you're located in the heart of town. We hope you have fun exploring!

Stunning NEW Modern Farmhouse, Just 3 Blocks from Healdsburg Plaza

Healdsburg, California, United States

Bed

Bath

Sleeps

$294.15

Your Healdsburg adventure begins at this 3-bedroom house. Less than a mile to all the action. Inside, guests find a marvelous king bed and two cozy queen beds, plus a comfy living room with a bonus trundle bed. Two bathrooms with tub or walk-in shower. Large redwood deck and garden is everyone’s favorite lounging spot. Our place with easy access north and south will help you experience everything Sonoma County has to offer.

Spacious house in marvelous Healdsburg close to town

Healdsburg, California, United States

Bed

Bath

Sleeps

$314.33

Welcome to Harold House, a lovingly renovated home in charming Healdsburg, California. The property sits within 15 minutes of everything you need to enjoy your time in wine country. You can walk to the lively downtown plaza, venture to the vineyards for wine tasting, stroll to Fitch Mountain for a hike, or wade in the Russian river. The property is designed for your comfort with beautiful and thoughtful interior touches, work-friendly capabilities and outdoor amenities for relaxation. brbrSee house highlights and reviews at @wherewestay_brbrOur property is in a safe and quiet residential area. The house is easily accessible, with no stairs and one small step in front of the house and to the garage. brbrThree bedrooms all feature luxuriously soft linens, ample closets and storage for your stay. The bathroom has a deep soaking tub and double sink vanity. A washer/dryer is available in the garage, which also has the Peloton bike available for guests to use. brbrThe kitchen is great for those who love to cook with Viking appliances, cooking amenities and spices. A Fellow Electric Kettle, Chemex and Nespresso should cover your coffee and tea needs. brbrFor remote work there are multiple workspace options inside with a desk that can be moved to your preferred working location. You can also work outside as the high speed WIFI extends to the outdoor dining area. When you’re not working the fenced in and private backyard also has a firepit, BBQ grill and lounge area for relaxation.brbrWe hope you enjoy the garden and property not just to view, but to eat! We encourage guests to pick from the garden (we have sage, basil, mint and rosemary for herbs as well as squash, zucchini, tomatoes and strawberries). We also have fruit trees that are young but already producing - peaches, meyer lemons, plums, figs and even artichokes. Take your pick!

Cottage

Chic wine country cottage and garden

Healdsburg, California, United States

3

Bed

Bath

6

Sleeps

$281.73

This charming 1 bedroom cottage is perfect for couples looking to explore the famous wine country of Sonoma's Chalk Hill Appellation. Surrounded by lush vineyards, you will enjoy all the amenities of home with top-of-the-line appliances, a queen bed in the bedroom and a full-sized sleeper sofa in the living room, full bathroom with bidet and stand-up shower. The kitchen is stocked with everything you need to prepare meals, and even an outdoor area that includes a gas fire pit under a cedar pergola and private driveway gate. brbrThe best part: it's only minutes from Healdsburg, Santa Rosa, Dry Creek and Alexander Valleys, and other popular destinations. Book now and enjoy a serene and memorable wine country experience!brbrTOT# 1361NbrbrSonoma County Quiet Hours 9pm-7ambrNo amplified music, parties or events allowedbrSmall well trained dogs allowedbrPlease note that the cottage does not have a washer and dryer

Cottage

Chalk Hill Cottage Close to Wineries

Healdsburg, California, United States

Bed

Bath

4

Sleeps

$769.0

What We Love About This HomebrThis sleek modern home features towering ceilings and walls of glass that showcase the stunning views. It features clean minimalistic design, neutral palettes, and warm woods.brbrThe two-level design features a dramatic Great Room and kitchen/dining area on the main level with three bedrooms on the upper level. The open design kitchen has generous prep space, and bar stool seating for four. The open dining area lies in front of the floor to ceiling windows, creating an epic view while dining.brbrThe open living area has floor to ceiling windows at both ends, and features comfortable couches and a massive oversized flatscreen TV.brbrAll of the rooms on the main level seamlessly connect with the outdoor deck and pool area, and the adjacent lawn with bocce court and corn ball field.brbrThe main house has three bedrooms upstairs, each with expansive views, and ensuite bathrooms. For additional guests, the den/office located just off the Great Room, easily converts to additional sleeping accommodations for weekend guests, and has its own ensuite bathroom.brbrA 1BR/1BA guest suite with amazing views is tucked below the main residence on the lower level, providing privacy and a separate entrance for guests.brbrJust 15 minutes from the quaint town of Healdsburg , home to popular wine industry events and a central plaza dotted with an abundance of tasting rooms and award-winning restaurants featuring the best in farm-to-table cuisines, art galleries and chic boutiques.brbrGuests staying at Dry Creek Moderno will enjoy access to BeautifulPlaces pre-arrival assistance. Our local staff can assist with pre-trip suggestions for winery visits, private chef dinners and any other special experiences you desire. On arrival day you’ll find a bottle of local wine and gourmet coffee waiting for you in your villa, and our team is available during your stay to answer any questions you have.brbrHouse RulesbrThis property is subject to local regulations governing vacation rental properties. Under local law, events, parties and outdoor amplified music are not allowed. Overnight and day time occupancy is limited to 8 guests, and rental guests must observe quiet hours between 9:00pm and 9:00am. The pool is heated Memorial Day through September. Note that the pool is not fenced or covered. brbrRates quoted on this page are subject to our revision. Rates are inclusive of 1 basic housekeeping visit each month, a utility credit, exit cleaning and booking fees. A $7,500 damage deposit is required.brbrThis residence is subject to a 30 night minimum stay in compliance with local regulations. Please contact BeautifulPlaces to discuss your needs, availability and terms.

Modern Mountain Top Retreat

Healdsburg, California, United States

4

Bed

4

Bath

10

Sleeps

$123.33

2nd floor Apartment -- Modern, Convenient, and ComfortablebrSeparate Entrance from main housebr500 square foot Unit featuring full kitchen, living room, bedroom and bathroombrQueen BedbrAir ConditioningbrWasher/Dryer in KitchenbrDishwasherbrOff Grove StreetbrEasy parkingbrEasy walk to HBG Plaza along Grove Street or along Foss Creek pathbrInternet includedbrElectric roller shades

Apartment

Clean, Modern 1 Bedroom Apt Built in 2019 -- Walking distance to HBG Plaza

Healdsburg, California, United States

Bed