Home Vacation Rentals By Owner In Healdsburg, CA

Showing 177 Of 177 Vacation Rentals
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Exceptional(1)

$1458.85

/ Nightly
Private Vacation Home

Healdsburg Luxe Reserve for 8, pool, spa, firepit

Healdsburg, California, United States

Healdsburg – A Luxury Smart Home With Pool, Hot Tub & Vineyard ViewsbrbrWelcome to Healdsburg Modern, a luxurious 3BR/3.5BA smart home located just 3.5 miles from downtown Healdsburg—one of Wine Country’s most sought-after destinations. This upscale two-story retreat offers resort-style amenities, seamless smart-home technology, and gorgeous vineyard views, making it ideal for travelers seeking a high-end Healdsburg vacation rental near wineries, cycling routes, food, and year-round events.brbrPerfectly positioned less than ten minutes from both Healdsburg Plaza and Windsor Town Green, guests enjoy effortless access to wine tasting, shopping, concerts, farmers markets, and local festivals. Its combination of privacy, convenience, and luxury makes this property a top choice for family vacations, wine weekends, remote work getaways, and romantic escapes.brbrLuxury Living & Smart Home ComfortbrbrStep inside to a light-filled interior designed for relaxation and connection. The open living room features:brbrComfortable sofas and chairsbrbrStone gas fireplacebrbrOversized smart TVbrbrBuilt-in workstation ideal for Zoom calls or remote workbrbrThe chef’s gourmet kitchen includes marble countertops, Wolf appliances (including a six-burner cooktop and double ovens—perfect for holidays), wine cooler, refrigerator, dishwasher, and seating for groups to gather and cook. A laundry room and garage access complete the ground floor.brbrThree Ensuite Bedrooms With Private BalconiesbrbrUpstairs, all three bedrooms feature:brbrPrivate ensuite bathroomsbrbrSmart TVsbrbrLuxury bedding, plush mattresses & extra linensbrbrDressing benches or chairsbrbrThe primary suite offers a private balcony with vineyard and backyard views, while the two guest rooms share a second balcony. Two oversized chairs in the living room fold out to sleep additional guests comfortably.brbrResort-Style Outdoor LivingbrbrDesigned for travelers who love outdoor living, the property offers:brbrIn-ground heated pool (May–Oct; optional heating fee outside season)brbrHot tubbrbrOutdoor kitchen with dining and lounge seatingbrbrGas BBQ & fire tablebrbrGardens, outdoor shower & open viewsbrbrThis beautifully landscaped outdoor space is perfect for relaxing after wine tasting, enjoying sunset dinners, or gathering with friends and family.brbrPermit: TVR21-0157brbrAdditional NotesbrbrAdditional contract required after bookingbrbrESA/service animals welcome without charge or weight limit however must be screened with WCLV after booking.brbrKey Features:br3 Bedrooms • 3.5 Bathrooms • Smart Home • High-Speed WiFi • Vineyard Views • Gas Fireplace • Heated Pool • Hot Tub • Outdoor Kitchen • Fire Table • Luxury Bedding
Bed 3

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Bath 3

Bath

Sleep 8

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Exceptional(133)

$1711.33

/ Nightly
Villa

Secluded Vineyard Estate Healdsburg

Healdsburg, California, United States

Mill Creek Estate is an exceptional Vineyard Estate located in the heart of the Sonoma Wine Country near the quaint town of Healdsburg and less than 6 minutes from the historic, upscale, and charming Downtown Plaza. The property consists of a main house and adjacent studio suite situated within an oak covered 15 acre setting. The gated property is nestled in the Sonoma foothills just west of town with views that are truly magnificent. From every direction one will see either intense natural beauty or miles of breathtaking gorgeous scenery. If extreme privacy is what you enjoy this is the place for your wine country vacation experience. brFrom Mill Creek Road, you will turn up a country lane which winds through an Oak covered forest across the gated 15 acre site to your doorstep. Reminiscent of homes built in early California, this 4 bedroom Estate has lots of exterior and interior stonework providing the perfect marriage of old world country charm and a casual, elegant California lifestyle. The living structures are tucked sensitively into the landscape under a canopy of trees which includes mature 500-year-old oaks. Designed for gracious country living, inside you will find walls of luxurious venetian plaster, vaulted and cathedral ceilings, wood and limestone flooring and abundant windows throughout the house. The views from inside the house are as breathtaking as the views from outside. br Mill Creek Vineyard Estate is the perfect place for family and friends to gather in a relaxing atmosphere of comfort and serenity. Surrounded by spacious terraces, gardens and lawn covered areas, this is the ideal vacation home for those who cherish the outdoors. With most rooms opening onto outside terraces you’re never more than a step away from natural serenity. With 2 covered Arbors and many other sitting areas to choose from, you will find just the right spot to savor a spectacular sunset, read in the afternoon sun or enjoy a candlelight dinner on a warm summer’s evening.brOutdoor amplified music is prohibited by local ordinance at vacation rental properties and also mandates strict outdoor quiet hours between 10:00 pm and 9:00 am.brbrSmoking is strictly prohibited inside the premises.brbrSwimming Pool - Please use safety cover when small children are around.
Bed 4

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Bath 4

Bath

Sleep 10

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Exceptional(6)

$894.06

/ Nightly
Private Vacation Home

Mill Creek by AvantStay | Modern Design, Patio, Hot Tub

Healdsburg, California, United States

Welcome to Mill Creek, your charming retreat located just 6 minutes from downtown Healdsburg and 1.5 hours from San Francisco. This stunning 2BR home boasts modern architecture and a cozy design that pairs perfectly with its lush, private, tree-surrounded setting. brbrStep onto the spacious patio, where you’ll find ample seating, string lights, a fire pit table, and a peaceful creekside backdrop—perfect for entertaining or simply settling into the sounds of nature. Designed with wellness in mind, the outdoor space invites you to slow down completely. Cool off with a refreshing dip in the plunge pool during warm afternoons, enjoy an evening soak in the private hot tub beneath the California stars, then unwind in the warm, tranquil sauna for the ultimate relaxation experience.brbrAll of this, just a quick drive to the vibrant downtown plaza. Come see why Healdsburg was just rated by Condé Nast Traveler as one of the top 10 small cities of America.brbrInside, the bright and airy open layout invites connection, from the sunny living room with its multiple sofas and a TV to the dining table and fully equipped kitchen with barstool seating and a full suite of appliances. Each of the two comfortable bedrooms features an ensuite bathroom, offering the ultimate in privacy and comfort.brbrMill Creek also offers the convenience of an in-home laundry room and easy parking. Whether you're relaxing on the deck, enjoying a meal al fresco, or exploring the beauty of Sonoma County, Mill Creek promises an unforgettable getaway.brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbrKnown for its vineyards, local cuisine, and nature parks, Sonoma County (45 minutes from San Francisco) offers a wide array of activities for those looking to retreat from city life. Touring local wineries, dining at farm-to-table restaurants, and visiting world-class spas are classic ways to experience the area. While unwinding is certainly the attitude in Sonoma, activities such as horseback riding, hot-air ballooning, and kayaking attract those looking for a little adventure. In the evening, watch the sunset over the vineyards and rolling hills, wine glass in hand.brbrLocal attractions: Downtown Healdsburg (6+/- min drive), 1.5 hours from San Francisco, central to 3 wine-growing regions: the Russian River, Dry Creek Valley, and Alexander Valley. Jordan Winery, Simi, Seghesio, Francis Ford Coppola, and Ferrari-Carano Gardens, among many other premium wineries. Nearby ranked restaurants include Single Thread Restaurant (3-star Michelin + rated in the top 50 restaurants in the world), Cyrus (1 Michelin star), and Auro (1 Michelin star). Near the Russian River, Healdsburg Ridge Open Space Preserve, Bodega Bay, and Point Reyes National Seashore. 20 minutes from Santa Rosa, Safari West, and Spring Lake Regional Park.brbrHome Truths:br- Guests will lose cell service approximately 2 minutes from the driveway. Be sure to have your door code handy or be prepared to connect to the Starlink Wi-Fi upon arrival. (Wi-Fi details can be found in the guest manual.)br- Please note: You won’t see filters at the sinks because the home has a whole-house filtration system—meaning all tap water is already filtered and safe to drink. It may have a stale taste due to the water source. A Brita pitcher is available for use.br- Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request.br- Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without AvantStay's approval, there is a fine of $500 per pet.brbrParking Details:br- Please make sure you park in the designated property parking locations only. If your home offers street parking please make sure you read all posted signage.brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation.brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees.brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. All bookings over 30 days require a security deposit.brbrWe report and prosecute all Credit Card Fraud.
Bed 2

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Bath 2

Bath

Sleep 6

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$196.0

/ Nightly
Private Vacation Home

Dragon Cottage | Historic house in Healdsburg with Russian River Valley views

Healdsburg, California, United States

Dragon CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled on the side of Fitch Mountain you'll find the Dragon Cottage! Boasting sweeping views of the Russian River, lush vineyards, rolling hills, and the mountain itself - there is never not something to look at. When you can pull yourself away from the home's breathtaking views and impressive interior, head for Camp Rose, a semi-private beach access point on the Russian River, or to the public Del Rio Woods Beach. Located in wine country, you can't miss out on the fabulous wine-tasting opportunities around you! Dry Creek Vineyard and Kendall-Jackson Wine Estate & Gardens are both less than 12 miles away.brbrAs one of the original Camp Rose homes, this historic charmer was originally built in the 40s. Its unique charm can be noticed through the small details like warm wood flooring, built-ins, and crown molding. Sit back and enjoy the comfort of the living room's ample seating and lovely views. Steps away, the home's full kitchen exudes a sense of retro charm with its checkered flooring. When mealtime rolls around, dine with your loved ones at the quaint breakfast table or at the expansive formal dining table.brbrPeaceful slumber and sweet dreams will come naturally in the home's five bedrooms. Keeping you cool and comfortable no matter the season, each room is embraced with a cool blast from the central air-conditioning. A private washer/dryer and board games round out the cottage's interior perks. brbrOutside, play a game of Ping-Pong under the California sun while the kids enjoy the playset or head up to the rooftop deck where you can be one amongst the trees. This home is subdivided into two units. Parking for one car and the unit you will occupy is on street level. brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide by The Good Neighbor Policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 2 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 5

Bed

Bath 1

Bath

Sleep 12

Sleeps

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$151.0

/ Nightly
Private Vacation Home

Rooster Cottage | House with Russian River views, hot tub, back deck, W/D, patio

Healdsburg, California, United States

Rooster CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to the peaceful home away from home that will have you relaxing in style! This gorgeous home was built in the 40s-50s and is part of the historic Camp Rose neighborhood and is nestled on the side of Fitch Mountain. There is a semi-private Russian River beach access called Camp Rose that is a half-mile walk down from the house. It is only for people in the Camp Rose community! There is also a public beach access called 'Del Rio Woods', which is about a mile up the road. Downtown Healdsburg is a short two-mile drive away where you will find restaurants, parks, endless vineyards and wineries. Some must-visit attractions include Dry Creek Vineyard, Trentadue Winery, Kendall-Jackson Wine Estate & Gardens, Luther Burbank Center For The Arts, Safari West, and Armstrong Redwoods State Natural Reserve.brbrThis beautiful retreat offers stunning views of the Russian River, vineyards, rolling hills, Fitch Mountain itself, and the birds that love to perch and soar overhead. Inside, this beautiful home away from home enjoy a sunny living area where you all can gather and plan your next adventures, a well-appointed kitchen with all the essentials and a Nespresso coffee maker, a sunny dining room with gorgeous views, and an attached laundry room with a washer/dryer.brbrThis home is subdivided into two units and the unit you will occupy is 5 to 6 steps down from the driveway which is at street level. You will have one designated parking spot in the driveway. Outside, on the level you occupy enjoy the extensive deck which boasts a private hot tub for your use only with views of the Russian River Valley. The deck also offers a convenient outdoor dining area, a sitting area with plenty of comfortable furniture, and a hanging egg chair. brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide by The Good Neighbor Policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 1 vehicle.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

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$486.85

/ Nightly
Agritourism

Charming Alexander Valley Farmhouse with loft, hot tub & a complementary tasting

Healdsburg, California, United States

Starlite Vineyards EscapebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrExperience the perfect blend of rustic charm and modern comfort at Starlite Vineyards, a stunning property located in the heart of Geyserville, CA. Nestled within the breathtaking vineyards of Alexander Valley, this enchanting retreat invites you to unwind in a beautifully restored 1912 farmhouse. With exclusive perks right on the grounds of the acclaimed Starlite Vineyards, your stay promises to be both relaxing and memorable.brbrStep inside to discover timeless elegance, featuring hardwood floors, crown moldings, and built-in cabinetry that seamlessly blend historic charm with modern amenities. The updated kitchen opens to a cozy family room, while formal living and dining areas provide inviting spaces for gatherings. With three spacious king-sized bedrooms and two full bathrooms, including a primary suite, this home is perfect for families or groups seeking comfort and convenience.brbrOutside, indulge in the serene beauty of the surrounding vineyards. Start your day with coffee on the deck, soak in the private hot tub, or explore the lush gardens. Your stay includes a complimentary wine tasting at the adjacent barn-turned-tasting room, where you can savor award-winning, boutique wines crafted from the unique terroir of the region.brbrAs part of a working vineyard, immerse yourself in the authentic rhythm of Wine Country. Depending on the season, you may witness the charming sight of vineyard workers tending to the vines. With ample amenities, including a gas grill, central AC, and internet access, Starlite Vineyards offers everything you need for a delightful getaway. Book your stay today and embrace the beauty and flavor of Alexander Valley!brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 4 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 2

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Bath 2

Bath

Sleep 6

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Exceptional(39)

$1551.85

/ Nightly
Private Vacation Home

Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)

Healdsburg, California, United States

Nestled on 10 acres in the prestigious Chalk Hill appellation of the Alexander Valley, this rustic, beautifully furnished, 5br/4.5ba, 3200 sq. ft., two-story lovely home with central heat/AC, sits on a wooded knoll just above the vineyards. A separate pool house on the opposite side of the circle drive combined accommodating 12 guests. Completing this wonderful retreat is an in-ground pool with cover, freestanding spa, and abundant, new outdoor furniture rests on a flagstone patio beside the pool with beautiful landscaping and lawn all around. This is pet friendly home with a pet fee.brbrThis beautiful Chalk Hill Compound is very well located with easy access to over 40 landmark Alexander Valley wineries including Lancaster, Verite, Chalk Hill, Hanna, White Oak, Field Stone, and Stryker, to name but a few. A spectacular and scenic 15-minute drive through the vineyard-graced valley, brings you to charming and historic Healdsburg, a world class Sonoma County Wine Country destination, with fine dining, shopping, and an abundant diversity of adventures and activities for your enjoyment.brbrEnter the property through the locked gate, up the paved circular drive, be welcomed by a center island with two mature oaks, and plenty of parking. On the other side of the drive, across from the main house, is the Pool House with full bath for your convenience, which also has beautiful landscaping around it and the pool behind. The main house has a large front entry deck with beautiful views and a wooded hill which slopes down to a seasonal creek. Front and west side decks include two outdoor tables for four with umbrellas, and a lovely 7’x8', 8-person Hot Springs freestanding hydrotherapy spa.brbrAll the features and amenities this beautiful property offers combine beautifully to create an idyllic setting for celebrations, family gatherings, and friendly get-togethers, just above the Alexander Valley vineyard floor. Your ‘home away from home’ is beautifully appointed and professionally decorated with everything you will need for a memorable and magical vacation experience.brbrNow up the flagstone pathway to the lovely main house with beautiful landscaping, abundant mature plantings and trees all around, and be welcomed by the entry hall with the well equipped, bright and airy, chef’s kitchen to your left. With two skylights and a central island featuring a GE 5-burner gas range with a retractable downdraft vent, a pass-through from the kitchen to the dining area provides two stools for the ‘backseat chefs’ and is a great place for planning your culinary artistry.brbrAdditional appliances include a new large side-by-side Kenmore freezer/fridge, GE dishwasher, and a self-cleaning Whirlpool oven and a new microwave on side. Additional kitchen necessities include a Cuisinart coffee maker, an extra large KitchenAid toaster, a new JA Henckels knife set, all new cookware, flatware, plateware, glassware, wine glasses, cutting boards, etc.brbrIdeally located for exploring the diversity of Sonoma County Wine Country, this property is a perfect ‘home base’ where you can relax and just soak it all in, or venture out in almost any direction for enjoying the many adventures nearby. There is an abundance of more than 100 award winning wineries within a short drive through the vineyards, in the Alexander, Dry Creek, Russian River, Sonoma, and Napa Valleys, as well as the towns of Healdsburg, Calistoga, St. Helena, Sonoma, and Napa; you will likely need at least a week to explore, experience, and enjoy it all, then return again and again for more relaxation, rejuvenation, and adventures. The Mayacama Golf Club is only 9 miles south.
Bed 6

Bed

Bath 4

Bath

Sleep 12

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Exceptional(2)

$488.06

/ Nightly
Private Vacation Home

Updated home w/ bocce ball court, large yard, deck & grill - Russian River views

Healdsburg, California, United States

Rio Lindo River RetreatbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled along the picturesque Russian River in Healdsburg, CA, this modern and updated home offers a unique retreat for upscale couples and wine enthusiasts. The property features two attached stacked units, with the main upper unit providing convenient street entry, while the lower unit is accessed by descending a short flight of stairs. Each unit boasts its own private patio, perfect for enjoying the serene river views and the gentle sounds of nature.brbrRecently renovated with an open concept design, the interiors are flooded with natural light, creating a warm and inviting atmosphere. The spacious yard includes a bocce ball court and a river dock, ideal for leisurely afternoons spent by the water. Guests can take advantage of the canoe available for use, or simply relax by the firepit under the stars.brbrThe property is a haven for those seeking adventure, with opportunities for kayaking, fishing, and hiking nearby. Healdsburg's charming downtown area, known for its wineries and fine dining, is just a short drive away, making this location perfect for a romantic getaway or a wine tour.brbrWhether you're looking to unwind in a tranquil setting or explore the vibrant local culture, this Healdsburg home offers the perfect blend of comfort and adventure. Book your stay today and experience the beauty of the Russian River!brbr**THIS HOME IS CONFIGURED AS TWO SEPARATE UNITS - ONE BEDROOM + BATH + KITCHEN UPSTAIRS & ONE BEDROOM + BATH w/KITCHENETTE + WASHER & DRYER DOWNSTAIRS. THEY HAVE SEPARATE ENTRIES VIA STAIRS ON THE OUTSIDE OF THE HOME. **brbr** PLEASE NOTE THIS HOME IS ON THE RUSSIAN RIVER - DURING HIGH WATER EVENTS THE LOWER UNIT CAN EXPERIENCE WATER INTRUSION **brbrParking notes: There is free parking available for 3 vehicles.brbrSecurity camera details: brbrDock details: brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

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Exceptional(15)

$629.87

/ Nightly
Private Vacation Home

Renovated farmhouse with vineyard views, bocce ball court, Ping-Pong, basketball

Healdsburg, California, United States

Bird and Barrel Vineyard FarmhousebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrExperience a fantastic and unforgettable getaway at this charming countryside farmhouse situated on one acre, surrounded by great wineries and beautiful vineyard views. This home away from home enjoys a private location, conveniently situated near the 101 freeway exit with easy access from a flat road. Bring your swimsuit and spend a day swimming or kayaking on the Russian River. Other fantastic attractions include Windsor Town Green, Dry Creek Vineyard, Kendall-Jackson Wine Estate & Gardens, Charles M. Schulz Museum and Research Center, Safari West, Armstrong Redwoods State Natural Reserve, and more.brbrStep through the gracious front porch into a bright, airy family room adorned with contemporary art and modern furniture, complete with a TV and a fireplace - a perfect space for relaxation, reading, and enjoying the provided board games. Continue the tour to discover a spacious, open-concept kitchen and dining area, fully equipped to prepare meals sourced from the Healdsburg farmer's market. Adjacent, a separate living area offers easy access to the back deck. Here, you will find a welcoming outdoor dining area and a hanging swing chair for birdwatching. Outside, a renovated barn awaits, featuring an eight-person veranda table, a Ping-Pong table, a library, and comfortable seating. Experience the sunset from two picnic tables next to the bocce ball court.brbrThings to KnowbrAn EV charger with both Tesla and CCS1 plugs is available for guest use at no charge.brCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide by The Good Neighbor and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 5 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

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Exceptional(27)

$1095.24

/ Nightly
Private Vacation Home

Cypress House & Studio, Walk to Healdsburg Plaza by RedAwning

Healdsburg, California, United States

Beautiful Mediterranean-style house just 2 blocks from the Downtown Healdsburgbrbrin Sonoma County. Open gourmet kitchen/dining/living room with French doorsbrbrlead to 3 view decks. 3 bedrooms, 3 full baths and a pullout couch - perfectbrbrcouples getaway to Wine Country. Gated entrance, private patio, and parkingbrbrgarage. EV charger on site! Studio & House can rent separately. Urban settingbrbrin a country town. Walk to everything Healdsburg.brbrbrbrCypress House is a perfect getaway with great outdoor spaces including rooftopbrbrand garden patios plus multiple balconies for enjoying amazing views of thebrbrtown. The house is designed with tall ceilings and beautiful Moorish tilebrbrthroughout to create a wonderful Wine Country feeling, situated in the centerbrbrof Healdsburg's great restaurants, wine tasting bars and shopping. The gourmetbrbrkitchen is ideal for entertaining, opening to dining and living rooms, as wellbrbras large private deck with amazing views of Healdsburg. Organic and Mexicanbrbrgrocery stores are right around the corner, like a house in Europe, perfectbrbrfor creating a fabulous meal with friends and family.brbrbrbrThis listing includes the whole house, two units which include 3 BR/3 Bath +brbrsleeping sofa, rooftop dining deck and 3-car garage. Perfect for couples andbrbrgatherings with friends and family.brbrbrbrOther things to notebrbrbrbrWi-Fi, high definition TV, gourmet kitchen with stainless steel appliances,brbrincluding gas range, convection oven, dishwasher, toaster, coffee maker, fullbrbrsize refrigerator, pots/pans/utensils and all tableware, washer and dryer.brbrKitchenette in first floor guest room Studio unit. Universal EV charger.brbrbrbr
Bed 2

Bed

Bath 3

Bath

Sleep 8

Sleeps

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Exceptional(14)

$622.44

/ Nightly
Private Vacation Home

Magnolia Ranch Vineyards | Historic house in Healdsburg with lovely private yard

Healdsburg, California, United States

Magnolia Ranch VineyardsbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrA true labor of love, Magnolia Ranch Vineyards was originally built in 1895 as a flower nursery. Since then, the home has been updated and modernized, yet it still holds an abundance of vintage charm. Enjoy the home's history while taking note of the crown molding throughout, original wood floors, decorative fireplace, and old-school furnishings. brbrThe living room offers a pleasant space to sit back, read, watch TV, and visit with the people who mean the most to you. Steps away, the modern kitchen radiantly gleams with its full suite of stainless steel appliances, center island, marble countertops, and farmhouse sink. Cook, bake, roast or broil with a brand new Induction/Convection oven for the chef at heart for those who love to bake. Off the kitchen, appreciate having access to a separate laundry room. brbrPeace can be found in the sunlight bedrooms. Amidst the soft linens, wooden furnishings, and central air-conditioning, you will feel right at home. brbrOutside, soak up the California sunshine from the two furnished patios, or indulge in a picnic under the grand walnut tree. While gazing up at the mountains, fire up the gas grill and host a sweet summer barbecue for your loved ones.brbrWhile here, you'll receive an extensive look at your surroundings. Delve into local agriculture, learn about biodiversity, explore family wine-making, and gain insight into sustainable vineyard practices. More than just a vacation, your stay will be an immersive experience blending relaxation and education. The owner even lives on-site and will offer this personalized introduction about the area to guests.brbrLess than 23 miles away from your stay, visit the area's numerous wineries, Luther Burbank Center For The Arts, Safari West, Armstrong Redwoods State Natural Reserve, and the Northwood Golf Club.brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide by The Good Neighbor Policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.brThe fireplace is not for guest use.brBe mindful of the local wildlife.brbrParking notes: There is free parking available for 2 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
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Exceptional(5)

$1982.4

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Private Vacation Home

The Ultimate Wine Lover's Experience

Healdsburg, California, United States

2013 marked the first year that this Iconic Sonoma County winery had ever opened up it's grand estate house to guests. This is the ultimate wine country experience for wine lovers. With one of the most magnificent views in wine country, sip on a glass of estate library wine by the pool as you overlook 4 different premium wine appellations. The house comfortably sleeps 8-10 with room for more dinner guests in the Estate House's grand dining room. In the mood for wine tasting There are 10 premium Russian River Valley wineries within 2 miles, the closest being about 20 steps away from your back door at the winery's own tasting room where you and all of your guests will receive complimentary VIP tastings experiences. In the mood for some serious after hour wine tasting Maybe a 10 year vertical of Cabernet Sauvignon with dinner The estate house comes with it's own private cellar where you will have full access to the entire wine history of the winery going back to the 80's. You are 5 minutes to world class dining in Downtown Healdsburg or we can arrange for our private wine country Chef to come to you and prepare a perfectly paired wine dinner as you watch the sunset over wine country from the grand dining room. Pool and brand new Hot Tub overlook miles of vineyards and open space. This property complies with Sonoma County TOT regulations, certificate number 1106N.
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Exceptional(109)

$361.2

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Cottage

WINE COUNTRY RIVERFRONT RETREAT WITH SPA & VIEWS

Healdsburg, California, United States

THIS COTTAGE IS A TRUE RETREAT. Our cottage has very reasonable rates for a house on the river with scenic views and a large spa. It is truly a different experience to be on the river. The large deck and dinning room have wonder views of the river and lots of natural light. Built in 1930 and updated over the year, keeping all the charm of a rustic vintage river cottage. There are high ceilings, wood floors, knotty pine in the living room, a stone fireplace with insert, granite counters, large double sink, gas stove, dishwasher, disposal, enclosed sun porch and large deck with wonderful river views. It is an old fashion river cabin that is pet and family friendly. It is not a modern high end home or fancy Healdsburg hotel. Just a fun place to enjoy the views, spa and river. The river flows behind the house just a few steps away. Take the path to the river in the summer time and enjoy our private gazebo set up for our guest to use with sun shade, table and chairs. A perfect place to hang out, relax and swim. A large 4 person hot tub is located under mature redwood trees, very private. The house is near the end of a quiet street with very little traffic. There is a one car garage plus 1 or 2 parking places in the driveway.brbrWe have all the comforts of home, central forced air heating, high speed internet, Netflix's, smart TV in living room, second TV in the back bedroom, Comcast cable TV. There are ceiling fans in the living room and dinning rom and portable fans in the bedrooms but there is no air conditioning. brbrWe set up a Gazebo/Sun Shade (summer only) across the river right on the river bank with table and chairs, provides lot of shade, we also have tubes for a river float, ice chest, beach umbrella and beach chairs for our guest to use (summer only) to take full advantage of all the river has to offer.brbrThe easy beach access makes it a fun place for children to enjoy the river. Take a float or swim down the river, enjoy the scenery, you may even see a few turtles and herons.brbrBesides the river there are many other activities for guest to enjoy, the Healdsburg Town Square is 3 miles away which offers shopping, fine dinning, theaters, bakeries, live concerts and a farmers market. Dry Creek, Alexander Valley and Russian River wine regions are just a short drive from the property with world class wineries and tasting rooms. brbrThe Villa Chanticleer, a wonderful facility for Weddings is less than a mile away on North Fitch Mt. Road. They also have a big dog park. Badger park has a play area for children. brbrThe house will accommodate up to 4 adults or a couple with 2 children. Works out well with 2 couples as the bedrooms are separate from each other, one in the front and the other in the back of the house, allows for nice privacy. If you are planning a wedding, family gathering or just have a larger group and need more room, the owners can refer you to additional rental properties near by. brbrHOUSE AND SONOMA COUNTY RULES: The following information is required by the County: Only 2 cars allowed at the house and must be parked in the driveway or garage. There is no street parking allowed.brbrMaximum occupancy is 4, children under 3 are not included. Maximum number of day guests allowed over the 4 night time guest is 2 for a total of 6 people. Please be respectful of our neighbors, many of them are permeant residences. Quiet hours are from 9:00 p.m. to 8 a.m. No amplified sound of any kind is allowed, including speaker attached to your phone.brbrWe are a pet friendly house (2 dog maximum). Dogs must comply with Sonoma Co. leash law.brbrTHANK YOU for following these rules so the area can be enjoyed by all, full time residence, vacation renters and second home families. brbrTOT#677N. Permit #ZPE11-0161brbrKeywords: Russian River, Wine Country, Wine Tasting, Cabin, Sonoma, Cottage, Vineyard, Scenic, Riverfront, Waterfront, Rafting & Tubing, Kayaking, Swimming, Family, Get A Way, Retreat, Romantic, Couples.
Bed 2

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Exceptional(2)

$2938.15

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Private Vacation Home

Sprawling Vineyard Estate - Pool, Hot Tub - Stunning Views!

Healdsburg, California, United States

Summary:brbrWorld class location with vineyard views in the heart of Dry Creek Valley!brbrbrbrThe Space:brbrPrivate wine country destination property surrounded by the vineyards, tasting rooms and restaurants that have made Healdsburg the crown jewel of wine country. brbrbrbr- Large wine country estate on 10 acresbrbr- 6 bedrooms/7 Bathrooms, multiple living spaces, library, dining rooms, large gourmet kitchenbrbr- Walk through the vineyard to the adjacent winery and tasting roombrbr- Secret entrance to our private beach on Dry Creek... brbrbrbrbrbr- Large Pool and Hot Tub in the middle of vineyardsbrbr- BBQ with outdoor dining brbr- Outdoor Showerbrbr- Poolside lounge with fire pitbrbr- Large and well-equipped gourmet kitchen.brbr- Separate dining room with seating for large groupsbrbr- Laundrybrbr- Self check-in brbr- WIFI brbr- Level 2 EV ChargerbrbrbrbrA picturesque drive to key destinations including:brbrbrbr- Healdsburg's Historic Plaza brbr- Dry Creek General Store brbr- Dry Creek Kitchenbrbr- The Madronabrbr- Geyservillebrbr- Lake Sonomabrbr- Alexander Valleybrbr- Russian River Valleybrbr- Sonoma Valleybrbr- CalistogabrbrbrbrGuest Access:brbrThe entire property is yours to enjoybrbrbrbrThe Neighborhood:brbrThis is the heart of Sonoma County... country roads, gentle rolling landscapes with picture perfect views everywhere you turn. A short drive will take you do world class wineries and restaurants as well as charming neighboring towns including Geyserville, Forestville, Sebastopol and Santa Rosa. The exploration of the this beautiful region is endless.brbrbrbrGetting Around:brbrNeed a car or car service...brbrbrbrOther Things to Note:brbrPool is only heated in the summer but is maintained throughout the year for those who enjoy a cool dip or a cold plunge. brbrbrbrPool HeatbrbrPool is heated during the summer months at no charge. Heating is offered from September 15th to May 1st for a daily fee of $150 (our cost is $200/day). Please provide at least 48 hours' notice in advance if you would like the pool to be heated before your stay. It is important to consider that heating the pool during off-season cooler temperatures may impact the maximum warmth the pool can reach.brbrbrbrHot Tub will be pre-heated for your stay.brbrbrbrInteraction with Guests:brbrWe are available via text or phone and are close to the property if a site visit is needed.
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