Vacation Home Rentals By Owner In Healdsburg, CA

Summary:brbrEscape to our charming Russian River bungalow just 6 min from Healdsburg Plaza. Enjoy river access, private hot tub, decks, rustic-modern comfort, and complimentary wine tastings!brbrbrbrThe Space:brbrRelax and recharge at Riverbend Retreat, a warm and inviting 3-bedroom, 1.5-bath bungalow nestled in a peaceful neighborhood just 5 minutes from Healdsburg Plaza. Perfect for couples, families, or a group of friends, this home blends rustic charm with modern comfort, offering an ideal base for exploring Sonoma wine country or simply unwinding by the river.brbrbrbrGuests 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.brbrbrbrLocal Winery Partnerships | Elevate Your Stay with Complimentary TastingsbrbrbrbrAs our guest, you’re invited to elevate your Wine Country stay with complimentary tastings at several small, locally owned wineries — (Guest of record must be present for all tastings)brbrbrbr• Merriam Vineyards – a family-owned estate crafting elegant, Old World–inspired Bordeaux-style wines; a $35 value per guest, complimentary for up to six guests.brbr• Orsi Family Vineyards – a locally loved winery specializing in expressive, small-lot Italian varietals like Sangiovese and Schioppettino; a $35 value per guest, complimentary for up to six guests.brbr• Stonemason Cellars – Small lot wines all sourced locally from Sonoma County grapes. Enjoy their Nibbles & Wine tasting experience; a $35 value per guest, complimentary for up to six guests.brbrbrbrA unforgettable way to toast your Wine Country getaway — cheers to delicious moments ahead!brbrbrbrThe Spacebrbr• Rustic charm + modern comforts: hardwood floors, open beam ceilings, crown molding, clawfoot tub, updated kitchen, smart techbrbr• Cozy sleeping for up to 6: 2 queen bedrooms + full-size bed in upstairs loftbrbr• 1.5 bathrooms, fully stockedbrbr• Fully equipped kitchen: French press, drip coffee maker, bean grinder, tea kettle, dishwasherbrbr• Front & back decks for lounging, gas BBQ, private hot tub under the starsbrbr• High Chair and Portable Crib available for guest usebrbrbrbrRemote Work & Year-Round Comfortbrbr• High-speed internet, Smart TV, cable, and peaceful surroundingsbrbr• Central heat, portable AC, washer/dryer includedbrbrbrbrOutdoor & Local Attractionsbrbr• Walk across the street to sandy river access for kayaking, swimming, or riverside picnicsbrbr• Just minutes from Healdsburg restaurants, tasting rooms, antique shops, hiking trails, and scenic drivesbrbrbrbrPerfect for GroupsbrbrRiverbend Retreat is on the same quiet street as Redwood River Lodge, Heron House, and River View Lodge. Rent multiple homes together for extra space, privacy, and shared riverside memories—ideal for family reunions, friends’ getaways, or wedding weekends.brbrbrbrExtras & Notesbrbr• Beach chairs availablebrbr• Max 3 vehicles, quiet hours 9PM–7AM, no parties/amplified musicbrbrbrbrExperience a peaceful Wine Country escape at Riverbend Retreat — with river access, modern amenities, and genuine hospitality for an unforgettable Sonoma getaway.brbrbrbrTOT#2284N | PERMIT#ZPE13-0262 | LIC#: LIC24-0890brbrbrbrThe Neighborhood:brbrLocated in a quiet Residential Neighborhood on the same street as our River View Lodge, Redwood River House, & Heron HousebrbrbrbrGetting Around:brbrLyfts/Ubers are available although wait times can vary.brbrbrbrOther Things to Note:brbrYou may also see this home listed as “River Retreat - Hot Tub and Tastings Included” on some booking sites.

Riverbend Retreat - Hot Tub and Tastings Included

Healdsburg, California, United States

2

Bed

1

Bath

6

Sleeps

$1,878

The property is situated on 4 acres of land, placed in the middle of the famous Alexander Valley. The listing available includes two conjoined homes: the main house and water tower. The water tower has access to all amenities the main house does, as well as similar features. The interior of the house is rustic chic with the comforts of a lux listing. The entire house can hold 4 adults, discounts are available if only two people rent just bottom floor.

Country chic cottage and connected water tower next to Jordan winery

Healdsburg, California, United States

Bed

Bath

Sleeps

$2223.5

Step outside and immerse yourself in a haven of outdoor delights. The centerpiece is a magnificent 40'×15' inground pool, complete with an inset spa, cover, and the ability to heat the water for your comfort. Relax on the surrounding patio, adorned with six poolside lounges and two spacious outdoor sofas, providing ample seating for ultimate relaxation.brbrFor al fresco dining, a charming outdoor dining table and chairs await on the new back Trex deck, just steps away from the pool area. Adjacent to it, a grand covered outdoor kitchen beckons with a six-burner cooktop, warming oven, two refrigerators, and an ice maker. As you explore further, you'll discover a second freestanding spa, a bocce ball court for friendly competitions, and a tiered entertainment area with a gas fire pit and comfortable seating. Sports enthusiasts will appreciate the half basketball court in the front area, perfect for a game of hoops.brbrGame Room with Separate sleeping area:brBut wait, there's more! The oversized detached 2-car garage, conveniently located near the pool, has been transformed into a game room. Challenge your friends to a lively game of ping pong or a round of pool on the 7-foot table. Relax in the large sectional seating area, featuring a brand-new 75 QLED 4K Smart TV, and enjoy the convenience of a powder room within arm's reach. Youngsters and vintage gamers alike will delight in the addition of a vintage Pac-man table with 30 games and an Xbox video game system. Above the game room, a private sleeping room awaits, adorned with a new king bed, a 75 QLED 4K TV, and an ensuite full bath.brbrMain house:brNow, prepare to be enchanted by the Heavenly Haven. To the right, a spacious entertainment area welcomes you, complete with a 75 QLED 4K Smart TV with SONOS sound system and a generously sized sectional for ample seating. The delightful, well-appointed kitchen is a chef's dream, featuring a stooled island, a Wolf six-burner gas cooktop with a griddle, KitchenAid double ovens, two KitchenAid dishwashers, and a large built-in Sub Zero pantry-style refrigerator. Adjacent to the kitchen, the private dining room offers a charming space with doors opening to the back patio and pool areas.brbrThe main level of the home boasts the exquisite Master Suite, featuring an ensuite bath, a walk-in closet, a new king bed, and glass doors leading to a small private patio. Another spacious bedroom on the main level awaits, with a king bed, a large new 75 QLED 4K smart TV, and a beautiful shared full bath just across the hall. Additionally, you'll find a well-appointed laundry room for your convenience. The second floor of the home features a shared bath, two large bedrooms, one with a balcony overlooking the pool, and an additional sleeping room, all furnished with king beds.brbrIt's time to book your stay and start planning your extraordinary Wine Country getaway. In addition to indulging in wine tastings and delightful food pairings at our world-class wineries, there's an abundance of adventures awaiting you. Explore the enchanting Armstrong State Park redwoods, discover the nearby Russian River, or take a short drive to the breathtaking ocean. Healdsburg also showcases the arts, with its array of beautiful galleries and incredible works to admire. Immerse yourself!brbrExplore the vibrant arts scene of Healdsburg, where creativity flourishes. Discover a plethora of beautiful galleries showcasing awe-inspiring works of art that will captivate your senses. For music enthusiasts, we have outstanding venues such as Weil Hall and the Green Center, renowned for their world-class performances. Don't miss the unforgettable experiences at the Luther Burbank Center for the Arts.brbrIn addition to these esteemed establishments, our town boasts numerous smaller clubs and venues that come alive with live music performances. Experience the rhythm and melodies that fill the air during the summer season, fall, and holiday festivities. From the Plaza to local wineries, there's always something enchanting happening in the form of music events.brbrWELCOME!

Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!

Healdsburg, California, United States

6

Bed

Bath

10

Sleeps

$1220.58

Summary:brbrWalk to Healdsburg Plaza while enjoying vineyard views, pool/hot tub, fire pit, gourmet kitchen, genuine hospitality, and complimentary tastings!brbrbrbrThe Space:brbrEscape to Private Vineyard Haven, a luxurious 2BR/2BA Sonoma home where modern comfort meets vineyard charm. Spanning 1,439 square feet, the home features a gourmet chef’s kitchen and floor-to-ceiling folding glass doors that open completely, blending indoor living with stunning views of your private Sauvignon Blanc vineyard and California sunshine.brbrbrbrThis home offers a perfect blend of comfort and care. Guests enjoy all the amenities while experiencing hospitality that makes them feel warmly welcomed and fully supported throughout their visit.brbrbrbrLocal Winery Partnerships | Elevate Your Stay with Complimentary TastingsbrbrbrbrAs our guest, you’re invited to elevate your Wine Country stay with complimentary tastings at several small, locally owned wineries — (Guest of record must be present for all tastings)brbrbrbr• Merriam Vineyards – a family-owned estate crafting elegant, Old World–inspired Bordeaux-style wines; a $35 value per guest, complimentary for up to six guests.brbr• Orsi Family Vineyards – a locally loved winery specializing in expressive, small-lot Italian varietals like Sangiovese and Schioppettino; a $35 value per guest, complimentary for up to six guests.brbr• Stonemason Cellars – Small lot wines all sourced locally from Sonoma County grapes. Enjoy their Nibbles & Wine tasting experience; a $35 value per guest, complimentary for up to six guestsbrbrbrbrA unforgettable way to toast your Wine Country getaway — cheers to delicious moments ahead!brbrbrbrLiving & Gathering Spacesbrbr• Spacious living room with slide-away glass doors connecting indoor spaces to the outdoorsbrbr• Reading room with daybed and queen dual-zone airbed for quiet momentsbrbr• Comfortable sectional with vineyard views and fresh airbrbrbrbrKitchen & Diningbrbr• Chef’s kitchen with stainless steel appliances, polished quartz countertops, and gas rangebrbr• Three-person breakfast bar + six-person dining tablebrbr• Fully equipped with cookware and gadgets for culinary creativitybrbrbrbrBedrooms & Bathroomsbrbr• Primary Suite: King bed, gas fireplace, high ceilings, en-suite bathroom with walk-in shower and double vanitybrbr• Guest Room: King bed with deck access and vineyard viewsbrbr• Smart TVs in both bedrooms, floor-to-ceiling glass doors, and convenient shadesbrbrbrbrOutdoor Amenitiesbrbr• Pool (14’x25’), hot tub, fire pit, bocce, cornhole, and BBQ (pool heating optional, fees apply)brbr• Back deck with vineyard and mountain viewsbrbr• Front deck with gardens, fountain, and scenic California countrysidebrbr• Ample outdoor seating for dining, relaxing, and stargazingbrbrbrbrLocation Highlightsbrbr• Less than 1 mile to Orsi Winery, the Healdsburg Plaza and local festivalsbrbr• Minutes from Healdsburg’s top wineries and restaurantsbrbr• Seghesio Family Vineyards 1.5 miles awaybrbr• Outdoor adventures nearby at Healdsburg Ridge Open Space Preserve (3.4 miles)brbr• Easy access to the Russian River and Sonoma CoastbrbrbrbrAdditional Detailsbrbr• Coffee: drip maker, Nespresso (Vertuo pods), bean grinder (coffee not provided)brbr• Complimentary Wi-Fi, games, books, stereo, washer/dryer, driveway parking for 2 carsbrbr• Max occupancy: 4 | Max vehicles: 2brbr• No amplified outdoor music; quiet hours: 9 PM–7 AMbrbr• Pool heating available seasonally (fees apply)brbrbrbrPerfect for GroupsbrbrPrivate Vineyard Haven is just two doors down from our Vineyard Vue—rent both properties together for larger gatherings, multi-family getaways, or wine country retreats with extra privacy and space.brbrbrbrExperience ultimate Wine Country relaxation at Private Vineyard Haven with vineyard views, luxury amenities, and genuine hospitality. Whether lounging by the pool, enjoying a sunset from the front deck, or tasting local wines, this home offers an unforgettable Sonoma getaway.brbrbrbrTOT#2283N | PERMIT#TVR21-0107 | LIC#: LIC23-0095brbrbrbrThe Neighborhood:brbrLocated in a quiet residential neighborhood, though it’s close to 101 and some guests note occasional freeway noise.brbrbrbrGetting Around:brbrUber and Lyft are available, though wait times can vary. The square is walkable, but part of the route goes under an overpass without a sidewalk.brbrbrbrOther Things to Note:brbrYou may also see this home listed as “Haven with Pool, Hot Tub and Tastings Included” on some booking sites.

Private Vineyard Haven with Pool, Hot Tub and Tastings Included

Healdsburg, California, United States

Bed

Bath

Sleeps

$2902.67

**Important** BEFORE you can request to book you must first reach out to us via Contact Host so we can determine whether you are a good fit. We are renting to guests - max of 8 - who are looking for a relaxing getaway and who will abide by our rental guidelines and treat our home with care. Please read the description below and the Please note section at the bottom of this section before reaching out. Thank you!brbrWhen our Healdsburg home burned completely in the 2019 Kincade fire, we were presented with the opportunity to start from scratch and create exactly what we wanted. While our new house is more modern than the last, we carried forward - and intentionally amplified - the characteristics we most loved: the expansive 360” views, the breezy and bright open floor plan, the ample opportunities for gathering indoors and out. The entire east facing side of the main house is floor to ceiling sliding glass doors which makes for a striking vista of the hills and vineyards beyond. We have included a photo of the original home so that you can see the transformation (note that reviews before prior to Sept 2019 reflect the old house).brbrPerched atop a hill, our home feels wonderfully secluded, yet restaurants, shopping, wineries and a myriad of outdoor adventures are just a short drive away and Windsor and Healdsburg are within 15 and 20 minutes, respectively. It's the kind of place where you immediately feel at home and will never want to leave. Note that VRBO places us in Windsor but we are in fact located in the Chalk Hill Area of Healdsburg.brbrThe property is ~7 acres and is comprised of a:br- two wing main house with 4 bedrooms that sleep 8. One wing has the primary bedroom, kitchen, dining and living room and the other wing has two queen bedrooms with a shared bathroom and a second king bedroom with an en suite bathroom.br- pool with in-ground spa; pool is heated mid May - mid Sept spa can be heated year round.br- pool house with a bathroom, office and all purpose tv lounge space + gymbr- expansive outdoor dining and lounge area which includes a built in BBQ, dining table that seats 10+ and a built in poolside lounge bedbr- garage equipped with a Tesla battery charger br- zone controlled radiant heat and air conditioning throughoutbrbrPlease note:br- We would like to get to know you a bit before we agree to offer a reservation. When you inquire, please let us know a bit about your group including how many you are (8 is the max allowed) and what brings you to the area.br- We do not allow weddings, large gatherings/events or parties of any kind. This is not the right house if you want to be loud, party or don't like following rules.br- We strictly adhere to the Sonoma County Rental Rules which include, but are not limited to, the following: quiet hours between 9PM - 7AM, No outdoor amplified sound allowed at any time. br- If we agreed to book note that we will ask you to sign a rental agreement for your stay; the template agreement (which will be tailored to you/your dates) is included in our listing and includes a complete list of rental rules.. brbrWe are fully permitted in Sonoma County as a vacation rental and we pay all required occupancy taxes and fees to the county [TOT Certificate 618N / Rental Permit No.ZPE13-0265/ LIC24-0442]

Modern Hilltop Healdsburg Residence With 360' Views

Healdsburg, California, United States

Bed

Bath

Sleeps

$2408.0

Brand new modern luxury home designed to maximize the natural beauty & surrounding calm. Perched on a hill surrounded by 100 year old oak trees, this spectacular home was built facing beautiful rolling hills and vineyards with ultimate guest comfort in mind. Enjoy your AM coffee watching a family of quails roaming the vineyard and end your evening with a glass of wine on the deck watching the sun set behind the golden vineyard hills. Located approx 3.5 miles (6min) from the Healdsburg Plaza

The Quails Crossing-Healdsburg Vineyard Home

Healdsburg, California, United States

Bed

Bath

Sleeps

$227.49

Summary:brbrCharming 2-bedroom, 2-en-suite Tuscan cottage just steps from Healdsburg Plaza. Enjoy a private patio, modern comforts, in-suite laundry, and complimentary wine tastings!brbrbrbrThe Space:brbrExperience the best of Healdsburg living at Heart of Healdsburg, a charming 2-bedroom Tuscan-style cottage just steps from the vibrant Healdsburg Plaza. This bright and airy retreat combines wine country charm with modern comforts, offering an ideal base for couples, families, or friends seeking an unforgettable Sonoma getaway.brbrbrbrWake up to morning sunlight streaming through your windows, enjoy coffee on your private patio, and soak in the peaceful surroundings before heading out to explore world-class restaurants, boutique shops, and acclaimed tasting rooms—all within walking distance.brbrbrbrInterior Highlights:brbr• Bedrooms & Baths: Two luxurious en-suite bedrooms. The primary suite features a queen bed, en-suite bathroom, and laundry area; the second bedroom has a full bed with private en-suite access.brbr• Living Space: Open and inviting layout perfect for relaxing after wine tasting or local adventuresbrbr• Kitchen: Fully equipped with modern appliances, drip coffee maker, bean grinder, pour-over setup, and kettlebrbr• Extras: High-speed Wi-Fi and thoughtful touches throughoutbrbr• Desk and Desk Chair available upon requestbrbrbrbrOutdoor & Location:brbr• Private yard with BBQ grill, ideal for alfresco dining or relaxing under the Sonoma starsbrbr• Just steps from Healdsburg Plaza, restaurants, tasting rooms, boutique shops, and local marketsbrbr• Close to redwood forests, hiking trails, and hundreds of wineries in Dry Creek Valley, Russian River Valley, and Alexander ValleybrbrbrbrHospitality & Guest Experience: Guests often highlight our thoughtful, attentive service, noting how we make every stay seamless and welcoming. While Heart of Healdsburg offers contactless check-in, you’ll feel genuinely cared for and supported by hosts who love the area as much as they love sharing it.brbrbrbrLocal Winery Partnerships | Elevate Your Stay with Complimentary TastingsbrbrbrbrAs our guest, you’re invited to elevate your Wine Country stay with complimentary tastings at several small, locally owned wineries (Guest of record must be present for all tastings)brbrbrbr• Merriam Vineyards – a family-owned estate crafting elegant, Old World–inspired Bordeaux-style wines; a $35 value per guest, complimentary for up to six guests.brbr• Orsi Family Vineyards – a locally loved winery specializing in expressive, small-lot Italian varietals like Sangiovese and Schioppettino; a $35 value per guest, complimentary for up to six guests.brbr• Stonemason Cellars – Small lot wines all sourced locally from Sonoma County grapes. Enjoy their Nibbles & Wine tasting experience ($35 value per person)brbrbrbrA unforgettable way to toast your Wine Country getaway — cheers to delicious moments ahead!brbrbrbrAdditional Notes:brbr• Garage access not included.brbrbrbrThe Neighborhood:brbrLocated in a quiet Residential Neighborhood. Walkable to the Healdsburg Plaza (roughly a 10 min walk)brbrbrbrGetting Around:brbrLyfts/Ubers are available although wait times can vary.

Heart of Healdsburg - Wine Tastings Included

Healdsburg, California, United States

Bed

Bath

Sleeps

$580.3

Summary:brbr10 Min. from the Healdsburg Plaza | Unwind at Rivers Breeze, a 2BR main house + private 1BR lower-level suite with separate entrance, riverfront decks, kayaks, & complimentary wine tastings!brbrbrbrThe Space:brbrSlow down, unplug, and breathe in the beauty of riverfront living at Rivers Breeze, a charming 2-bedroom, 1-bath main house with a private 1-bedroom, 1-bath lower-level suite, nestled along a peaceful stretch of the Russian River, just minutes from downtown Healdsburg and nearby wedding venues. Perfect for couples, families, or friends, this retreat invites you to reconnect with nature, loved ones, and yourself.brbrbrbrWe pair the comfort and charm of the home with hospitality that truly shines. From check-in to check-out, we’re here to ensure your stay feels effortless, welcoming, and stress-free.brbrbrbrLocal Winery Partnerships | Elevate Your Stay with Complimentary TastingsbrbrbrbrAs our guest, you’re invited to elevate your Wine Country stay with complimentary tastings at several small, locally owned wineries — (Guest of record must be present for all tastings)brbrbrbr• Merriam Vineyards – a family-owned estate crafting elegant, Old World–inspired Bordeaux-style wines; a $35 value per guest, complimentary for up to six guests.brbr• Orsi Family Vineyards – a locally loved winery specializing in expressive, small-lot Italian varietals like Sangiovese and Schioppettino; a $35 value per guest, complimentary for up to six guests.brbr• Stonemason Cellars – Small lot wines all sourced locally from Sonoma County grapes. Enjoy their Nibbles & Wine tasting experience; a $35 value per guest, complimentary for up to six guests.brbrA unforgettable way to toast your Wine Country getaway — cheers to delicious moments ahead!brbrbrbrThe Spacebrbr• Main Level: 2 bedrooms, 1 full bath, queen sleeper sofa in living areabrbr• Lower-Level Suite: Private 1-bedroom, 1-bath suite with separate entrance via back deck and stairs, perfect for guests seeking privacybrbr• Cozy Cabin Comfort: Warm wood accents, rustic furnishings, and an open layout for gathering or relaxingbrbr• Kitchen & Dining: Fully stocked kitchen with 12-cup drip coffee maker (coffee not supplied), dining space, and peaceful river viewsbrbr• Heat and AC ensure year round comfortbrbrbrbrOutdoor & Riverfront Featuresbrbr• Expansive deck with dining & lounge seatingbrbr• Adirondack chairs for riverfront relaxationbrbr• 2 kayaks + 2 life vests includedbrbr• Picnic table for evening wine and stargazingbrbrbrbrLocation Highlightsbrbr• 5 minutes to Ru’s Farm & Front Porch Farmsbrbr• ~10 minutes to Healdsburg Plaza for shopping, dining, and wine tastingbrbr• Easy access to local wineries, tasting rooms, scenic drives, and hiking trailsbrbrbrbrExtras & Notesbrbr• High-speed Wi-Fi, on-site parkingbrbr• Pet-free propertybrbr• No dishwasherbrbr• As noted above, the downstairs bedroom and bathroom are separate from the main house and are accessed via a private exterior entrance (no interior connection).brbr• Quiet, peaceful setting ideal for unwindingbrbr• On-Site Washer and Dryer availablebrbr• For everyone’s safety, and due to our high fire-risk location, guests are asked not to use the indoor wood-burning fireplaces.brbrbrbrAccessibility:brbrNo steps from parking throughout main level of homebrbrDownstairs studio suite and river require stairs to accessbrbrbrbrEnjoy a serene Wine Country getaway at Rivers Breeze, where riverfront views, modern comforts, and genuine hospitality create an unforgettable Sonoma experience.brbrbrbrPermit #: TVR23-0081 | TOT #: 4690N | LIC #: 23-0008brbrbrbrThe Neighborhood:brbrLocated in a quiet Residential Neighborhood. Property is in a rural setting.brbrbrbrGetting Around:brbrLyfts/Ubers are available although wait times can vary.brbrbrbrOther Things to Note:brbrYou may also see this home listed as “Riverfront getaway with Wine Tastings Included” on some booking sites.

Rivers Breeze - Wine Tastings Included

Healdsburg, California, United States

Bed

Bath

Sleeps

$2044.0

Surrounded by beautiful hillside vineyards, our home has 360 degree views that make you feel like you're on top of the world. Expect to say wow when you arrive! A serene retreat with a gated pool, hot tub, grills, fire pit, olive tree grove outside and 4BR/4.5BA expansive home with every amenity. The 4300 square feet allow spaces to gather and places to retreat with vineyard views from every window. We have a private chef, yoga instructor and winemaker available to make your stay even more memorable. You won't ever want to leave!brbrKITCHEN & DININGbrThe chef in your group will appreciate the gourmet kitchen with a six-burner chef’s range, wine fridge, food processors/blenders, stand mixer with pull-out shelf, and a 30” flat screen TV. Expansive counters, two sinks, All-Clad cookware, microwave, and dishwashers make your wine country culinary experience effortless. And if you prefer, you can work with our private chef who can handle a special dinner or all of your meals as you wish (additional fee). A separate butler’s pantry is stocked with table linens and napkins, extensive glassware, and espresso cups/saucers. Morning coffee options include Nespresso Vertuo, 14 cup drip, or electric kettle pour-over. A walk-in pantry is stocked with specialty olive oils & vinegars, spices & staples, and storage containers for your convenience.brThere are three dining areas; a lovely dining room which seats 10-12 and has French doors that open to the pool area, an informal table for 8 next to the kitchen for more casual meals and cooking demonstrations, and poolside. Beautiful glass-door cabinets store dinnerware for 12 for both indoor meals and outdoor dining as well as serveware for those family style dinners and cocktail parties.brLIVING AREASbrEnjoy vineyard and Cypress tree views from the large living room which has a fireplace and is adjacent to the dining room. There is also tv room just off the kitchen area which has a fireplace, a wet bar stocked with glassware, a 65 Smart Roku TV with DIRECTV, Sonos music built-in speakers, and the coziest Italian leather sofas which all recline to make movie nights a hit. Books, backgammon, chess, and other games are stored in the built-in bookshelves.brBEDROOMS & BATHSbrFind quiet privacy in the master bedroom with a four-poster king bed, sofa, 43” flat screen Smart Roku TV w/DIRECTV, and the most stunning view off the walk-out balcony with patio seating for sunset cocktails and early morning coffee. There is an adjoining sitting area with a fireplace for cozy evenings curled up in the chaise chair with a book. The master bathroom is equally stunning with floor to ceiling windows, separate tub, shower with vineyard view windows, and two large sink/vanity areas which connect to an enormous walk-in closet. brThere are three additional rooms on this level. The second bedroom has a king bed and the third bedroom has a queen bed, with both rooms offering exceptional vineyard views. These rooms connect through a large bathroom with a walk-in shower, two sinks and wall mirrors.brThe fourth room on the second story is equipped as an office for those “work-from-home” days with a large desk, printer and monitor as well as a leather sofa and side chair but it can also be used as a sleeping area. An electric inflatable twin Frontgate bed and feather bed cover is in the closet for your convenience and a full bath with large tub, separate walk-in shower, and two sink vanities can be used for this room or by the third queen bedroom next to it.brThe downstairs bedroom has two twin beds which can be put together as a king if desired. This room has a large walk-in closet and an ensuite bathroom with a walk-in shower. This is the best room for anyone in your group who prefers to be on the ground level for easy accessibility.brThere is also a guest bathroom downstairs off of the front foyer.brOUTDOOR AREASbrYour own resort outdoors will be hard to leave once you experience the large private pool, hot tub, grills, outdoor refrigerator and a spacious patio with ample seating and dining tables. We have chaise lounges, pool towels, water fountain feature, and grassy areas for kids to play all inside the gated veranda. Beautiful landscaping and flowers surround you here and an impressive olive grove of 20 trees awaits on the other side of the gate. We love to have a cup of coffee in the morning sitting at the table in the olive grove overlooking the vineyards and listening to the birds chirping. This is also a wonderful area for an outdoor lunch or cocktail reception. There is also a fire pit perched on the edge of the hill providing yet another spot for gathering. And feel free to enjoy fruit from one of our trees which include orange, blood orange, grapefruit, peach, and lemon! We have a large parking area outside as well as a three car garage. Open the far-right garage bay and use the exercise equipment there to experience an indoor-outdoor work-out. We have yoga mats, exercise mat, upright rower, weights, kettlebell, stability ball. And of course, the vineyards are magical. We have close to ten acres of vineyard which surround the house on all sides. Our winemaker can arrange a special tasting or walk through the vineyard with you if you’d like to learn more while you are there.brEXTRA AMENITIES & DETAILSbrGuest amenities include complimentary Wi-Fi, a washer/dryer with laundry chute from the second floor, and driveway parking for up to 6 vehicles. We have DIRECTV and Roku enabled TVs to allow you to access your streaming apps. We have a Sonos music system with speakers indoors and outdoors. This property offers three fireplaces. brbrAdditional house cleaning services are available during your stay for $350/cleaning.brWe also have a generator in case of any power outages in the area.brbrSPECIAL EVENTS: We can also help you plan and host private events at the house or at Limerick Lane Cellars winery just up the street...special occasions like birthdays, rehearsal dinners, and anniversaries. We are also able to host corporate offsites and group experiences. Just let us know what you have in mind. Additional fees/costs for events. Send your inquiry to www.limericklanewines.com/eventsbrbrTHE LOCATIONbrDowntown Healdsburg is known as one of the most charming towns in America. The restaurants are fantastic and there are close to 20 wine tasting rooms, boutiques and galleries downtown which is just 3 miles away. We know the area well and can provide suggestions and special experiences through our long-standing relationships.brSonoma County Regulations: (TOT# - 4080N)brMax occupancy 10 overnight , 16 during the day (does not include children under 3 yrs)brMax occupancy doesn't apply to Easter, Memorial Day, July 4th, Labor Day, Thanksgiving, Christmas Eve, Christmas.brMax vehicles is 4 overnightbrNo amplified outdoor music anytimebrQuiet hours 10pm – 7ambrFire Pit must be turned off if unattended and by 10pm, no other outdoor fires permitted.brIf you need anything before, during, or after your stay, our lovely property manager is just one call away.

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Healdsburg, California, United States

5

Bed

Bath

10

Sleeps

$1015.03

Welcome to Bradford House — a beautifully designed shingle-style estate set on four private acres in the heart of Healdsburg wine country. With a resort-caliber pool, lush manicured gardens, and seamless indoor-outdoor living, this is one of Sonoma County's most distinctive private retreats.brbrThe home's architecture channels a classic East Coast Hamptons shingle style facade with crisp white trim, Italian cypress, and a grand motor court arrival. Inside, every room has been thoughtfully designed with premium finishes, high ceilings, and an effortless flow between indoor and outdoor spaces.brbrWith multiple living spaces, large kitchen, formal dining for the full group, a private bar and study, and a covered loggia that functions as a genuine outdoor living room year-round, and fitness center, the property is as well-suited to a lively group gathering as it is to a quiet, restorative escape. brbrStarlink high speed internet, solar field and Tesla battery panels ensure continuity of operation despite the property's private setting. Baby and children's essentials are also available upon request. brbrBradford House sits within Dry Creek Valley, one of Sonoma County's most distinguished appellations in California's premier wine country - a sun-warmed corridor celebrated for its Zinfandel and Cabernet Sauvignon. brbrHealdsburg, ten minutes south, is consistently ranked among California's premier wine country destinations. Bradford House sits minutes from three of Sonoma's most celebrated AVAs and a short drive from downtown Healdsburg's celebrated plaza, where you'll find Michelin-starred SingleThread, the Dry Creek Kitchen, and some of the most compelling independent wine bars and restaurants in Northern California.brbrThis residence is subject to a 30 night minimum stay in compliance with local regulations. First time renting this Summer and Fall!

Bradford House — A Private Estate in the Heart of Dry Creek Valley

Healdsburg, California, United States

Bed

Bath

Sleeps

$275.28

Summary:brbrDesigner Wine Country retreat just 2 blocks from Healdsburg Plaza. Fitch Street Escape features 2 bedrooms, 2 baths, seamless indoor/outdoor living, and complimentary wine tastings!brbrbrbrThe Space:brbrStep into Fitch Street Escape, a chic and recently remodeled historic home just 2 blocks from Healdsburg Plaza. Perfectly located in the heart of Sonoma Wine Country, this sophisticated retreat offers easy access to award-winning restaurants, boutique shopping, and world-class wine tasting.brbrbrbrBlending modern design with historic charm, this bright, open-concept home features 2 bedrooms, 2 full bathrooms, and high-end finishes throughout. A chef’s kitchen with stainless steel appliances, sleek surfaces, and an inviting island makes cooking a pleasure, while indoor/outdoor living is elevated by large Bonelli sliding doors connecting the kitchen to the private backyard.brbrbrbrHighlights & Amenitiesbrbr• Bedrooms & Baths: 2 bedrooms, 2 full bathrooms, sunken clawfoot tub, gas fireplace for cozy eveningsbrbr• Indoor Comfort: Open floor plan, smart TV, Bluetooth speaker, stylish furnishings, thoughtful culinary touchesbrbr• Outdoor Living: Front porch swing, backyard seating, fire table, ideal for relaxing or entertainingbrbr• Prime Location: Just blocks from Healdsburg Plaza for dining, wine tasting, and local eventsbrbr• Pet-Friendly: Up to 2 pets welcome (pet fee applies)brbrbrbrHospitality & Guest Experience: Guests often highlight our genuine hospitality and attention to detail. While Fitch Street Escape offers contactless check-in, our team ensures you feel warmly welcomed, well cared for, and supported throughout your stay—by hosts who know and love Sonoma Wine Country.brbrbrbrLocal Winery Partnerships | Elevate Your Stay with Complimentary TastingsbrbrbrbrAs our guest, you’re invited to elevate your Wine Country stay with complimentary tastings at several small, locally owned wineries (Guest of record must be present for all tastings)brbrbrbr• Merriam Vineyards – a family-owned estate crafting elegant, Old World–inspired Bordeaux-style wines; a $35 value per guest, complimentary for up to six guests.brbr• Orsi Family Vineyards – a locally loved winery specializing in expressive, small-lot Italian varietals like Sangiovese and Schioppettino; a $35 value per guest, complimentary for up to six guests.brbr• Stonemason Cellars – Small lot wines all sourced locally from Sonoma County grapes. Enjoy their Nibbles & Wine tasting experience ($35 value per person)brbrbrbrA unforgettable way to toast your Wine Country getaway — cheers to delicious moments ahead!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 the Plaza and surrounding neighborhoods.

Fitch St Escape - Wine Tastings Included

Healdsburg, California, United States

Bed

Bath

Sleeps

$485.0

Step into this beautifully updated mid-century modern house and enjoy the beautiful garden, the serenity, and the attention to every detail that anticipates your every need.brbrAn oasis of calm. The house is full of light, art, and views into the private garden. Beautiful open living, dining and gourmet kitchen, with doors that flow seamlessly from inside to outside.brbrUse this as your luxurious home away from home. Venture out to enjoy the farm fresh flavours of Healdsburg's many top rated restaurants and local organic markets. Cook up a storm in the HUGE fully-stocked kitchen.brbrExpand your knowledge of Sonoma's phenomenal wines. Healdsburg is where three well known appellations meet: Russian River, famous for Pinot Noir; Dry Creek, known for Zinfandel; and Alexander Valley, for its high-elevation Cabernet Sauvignon and Syrah; and all three for superb Chardonnay. Enjoy this magical place with your family and friends, sharing wonderful meals and starlit evenings. Then sink into fabulous bedding in complete peace and quiet until waking up to another day in paradise.brbrA bit of planning is called for if you are to explore dozens of nearby wineries and still have time for cycling, hiking, shopping, visiting the Sonoma coast, and enjoying all the wonderful things Sonoma has to offer. Uber has arrived, adding another option to wine-country exploring!brbrMore about our Garden: Peaceful, private, large and sun-filled, with landscaping that creates zen-like tranquility. An amazing surprise in the heart of town, handy to all the town square has to offer (restaurants, shops, farmers markets, gourmet and organic grocery stores, and, of course, wine tasting). You feel the peace of total privacy once you step into the garden. With views to enjoy, you can wander into the year-round herb garden, or pick your own sun-ripened cherry tomatoes, to supplement your culinary activities. Help yourself to Meyer lemons, oranges, limes in season, and watch the walnut tree ripen! Seasonal highlights change, but this garden is beautiful all year long.brbrAm I Inside or Out: California living at its best, the house flows onto decks and into the garden. The decks are designed to provide dappled shade, comfortable even in the summer sunshine, plus heaters to ward off the early morning or late evening chill. The French doors pull you into the garden, the house seamlessly flows outside, making the living and entertaining space enormous. Inside feels like a stylish loft - open, with comfy down-filled sofas to relax in with a book and glass of wine. Beautiful antiques, Persian carpets on the dark hardwood floors, and stylish ice-blue walls, make you want to stay forever. Bring your i-Phone and fill the house with the music that you love the most. Dimmer switches throughout and beautiful lighting lets you set the mood that you want. A real wood-burning fireplace in the living room banishes any cool evenings, while you watch Direct TV or a streaming service, or nestle into the den and flip through cook-books planning tomorrow's gourmet adventure.brbrBedroom Choices/Kitchen Delight: Bedrooms: Hate to decide who gets the nicest bedroom This house is perfect! It has two master suites and a third bedroom with a beautiful full bathroom right across the hall! Three couples can enjoy total privacy and each be in love with their own room.brbrKitchen: The heart of any home, ours is a gourmet entertainer's dream - Gas Range, with grill, two ovens, and two huge sinks, plus loads of counter space. For us, cooking is a group activity - plenty of room for all who want to pitch in! For the spectators, bar stools overlook the action. A few steps take you to the covered barbecue area, and the choice of an outside dining table or beautiful indoor dining. Everything you need is at hand - from high-end Henkel knives, Calphalon pots and pans, to Sophie Conran china (service for 12), cloth napkins, beautiful serving dishes, and a Nespresso coffee machine that turns out espresso, cappuccino, and more! A chef's dream, the perfect place to create delicious meals together to accompany the spectacular wines you've just discovered.brbrThis Healdsburg home is magical - romantic and serene with beautiful surroundings inside and out. Classic California easy living with a house that opens into a private garden. Use our yoga mats to start the day with yoga on the deck while watching the sun rise. End the day with a glass of wine on our elegant lounging furniture looking at the golden sun set over a beautiful open sky. In-between go exploring, on foot, by bicycle, or by car - you'll be occupied with restaurants, tasting-rooms and shops, but it takes only minutes to be in the countryside, with endless choices of country roads to find and follow! The night sky is full of stars, and the garden has subtle landscape lighting, so tuck yourself into the outdoor jacuzzi tub and stargaze in a way that simply isn't possible in a city. If you want to combine rest and exercise (the ultimate way to return home refreshed) it is so easy, take the bikes for a spin, or take a hike on the well marked trails at the nearby Healdsburg Ridge Open Space Preserve.brbrCalling all cyclists: Healdsburg is made for cyclists of all levels. We have six Trek bicycles that you can use and there is a bike rental shop in town, or, if you are elite cyclists, bring your own! You can mosey along the gently rolling hills of Dry Creek Valley (our favourite ride is out West Dry Creek Road and back on Dry Creek Road - either a 12 mile loop or a 22 mile loop - both of which are spectacular). Zoom up to Geyserville, or use our maps to find the super challenging hills! If the concept of exercise is better than the reality - cycle to The Quail and Condor Bakery, Costeaux, Little Saint, or The Acorn Cafe for breakfast or lunch, or take yourself to one of the nearby wineries for a picnic!brbrAmazing restaurants and wineries: Check them out - wonderful wines from Russian River Valley, Dry Creek Valley, Alexander Valley, Chalk Hill, Knights Valley, Napa Valley and Anderson Valley are all a beautiful easy drive from your home-base! You can stroll into town and enjoy world-class restaurants including the highly acclaimed Single Thread (warning - book ahead and be prepared to participate in a truly amazing, but expensive, evening), also acclaimed are Dry Creek Kitchen, Valette, The Madrona, The Matheson and their rooftop bar Roof 106. For more casual dining, but with truly amazing food and ambiance, our favourites include Bravas (Spanish tapas, with an amazing back garden and bar), Lo & Behold (small plates perfect for sharing, also with beautiful outdoor seating), Bistro Laginappe (a stunning new French bistro, with a fun outdoor space), and Willi's Seafood (small plates, amazing ceviche, and a very fun bar!) If you want to venture further afield, Diavolo in Geyserville has arguably the best pizza in the world - and they make their own sausages. Cyrus has reopened in Geyserville - already with a Michelin star! And it is easy to explore the emerging restaurant scene in the hamlets along the Russian River, or take Hwy 128 over the top to Napa - and visit the stylish Solange, or Greystone at the Culinary Institute of America, or many others like Bouchon, Bistro Jeanty and RH Kitchen further away in Yountville. Tip - drive the Silverado Trail not Hwy 29 through Napa Valley - way prettier, and possibly faster by skipping in-town Napa traffic jams (or just stay in the prettier and more relaxing Sonoma Valley)! If you have an Electric Vehicle, we have a Level 2 charging port.

Sunset Magazine Meets Healdsburg - Foodies & Wine Lovers

Healdsburg, California, United States

3

Bed

Bath

6

Sleeps

$394.74

Perched on a 40-acre hilltop among the grapes at Lavender Hill Vineyards, Dry Creek Villa offers a serene retreat where you can enjoy breathtaking views, complete privacy, and nights so quiet you may never sleep better. It's just 12 minutes to the downtown Healdsburg plaza and is very close to many award-winning wineries. Lake Sonoma is 10 minutes up the valley. The iconic Dry Creek General Store is a short drive away.brbrThe airy main room features vaulted ceilings, bamboo flooring, and large windows that flood the space with natural light. It includes a dining table for six and a comfortable queen sofabed for additional sleeping space. The full electric kitchen is equipped with granite counters, a dishwasher, and everything needed for light snacks or a gourmet feast.brbrYour restful nights are assured in two stylish bedrooms, each furnished with:br• A contemporary queen-size platform bed.br• An ultra-comfy premium mattress.br• Quality linens.br• Room-darkening window coverings.br• Bedside reading lamps..brbrThe spacious bathroom, with vessel sink and oversized shower, is conveniently accessible for all guests.brbrOutdoor Living & Relaxation.br• Grill your favorite foods on the gas BBQ.br• Soak in the secluded, six-person hot tub set right beside the vines, perfect for stargazing.br• Rinse off under the private outdoor hot-water shower.br• By prior arrangement and if available, you may enjoy a dip in the 48 ft. solar-heated lap pool at the owner's personal residence nearby (seasonally, approximately May to October).brbrEntertainment & Work.br• Enjoy a movie night on the 42 Sony smart TV with Dish satellite channels, or connect to your own streaming accounts. br• Listen to your favorite music from the in-ceiling speakers and audio receiver using Bluetooth.br• Unwind with a selection of board games, puzzles, and reading materials.br• A built-in desk and property-wide Wi-Fi are available if you need to connect.brbrGuest Access.br• Guests will have private access to the entire villa and its immediate surroundings, including the private hot tub, gas BBQ, and outdoor shower. Entry is seamless with self check-in; you will receive a unique door code that is valid for the duration of your stay.brbrInteraction With Guests.br• We respect your privacy and offer self-check-in for convenience. We may greet you upon arrival or stop by briefly to say hello and ensure you have everything you need for a wonderful visit. As your hosts, we are happy to share our local knowledge and insider's list of things to do, places to visit, and introductions to winemakers and restaurateurs.brbrOther Details to Note.br• Your reservation confirmation is subject to signing our rental agreement which must be completed within 5 days of booking.br• A security deposit hold of $500 will be placed on your credit card two days prior to arrival.br• A 3.25% processing fee applies to bookings where a credit card is used. Other payment types (check, electronic transfer or currency) will not incur this fee. br• No outdoor amplified music allowed.br• Maximum of three vehicles parking overnight. br• This property is a licensed and permitted vacation rental (License: LIC24-O261, TOT: 6O9N).br• By contacting us through this website, you give us express permission to contact you regarding this or future rental offers. br• Any Service Fee shown is automatically added and collected by the booking platform and is not paid to owners.br• All descriptions, pictures and text herein are Copyright of Lavender Hill Vineyards, LLC.

Private and Quiet Vineyard Villa with Hot Tub

Healdsburg, California, United States

Bed

Bath

Sleeps

$1,262

Our home is a contemporary ranch, modern yet comfortable, and surrounded by nature with plentiful outdoor space to explore. The property is also extraordinarily private, with little to no visibility from neighbors of the house and its surrounds.brbrThat said, we are mere minutes from some of the best wineries in Healdsburg. Some of our favorites include Lambert Bridge Winery, Quivira Winery, and Unti Vineyards. Grab a sandwich at the Dry Creek General Store (5 minutes away) and start vineyard hopping, then return for a soak in the hot tub under the stars.brbrStart the morning off right with coffee on the patio (we have a Nespresso, a Moccamaster, and a French press for traditionalists). Try Diavola Pizzeria & Salumeria, Campo Fina, or Dry Creek General Store for lunch, then head back home for an afternoon nap, or enjoy a long, hot shower in one of the two outdoor showers (they've been described as better than therapy by former guests). Take advantage of our fully-equipped kitchen, outdoor grills (both gas and wood-burning), and expansive deck with trellis for meals; or venture out and try Healdsburg's plentiful restaurant options (we love to make recommendations)! brbrAfter a long day out exploring or wine tasting, spend some lazy time relaxing in the comfy living room, in the screened-in porch in front of the wood-burning stove, or around the fire pit (nestled in the garden) with a glass of wine. Don’t miss a dip in the hot tub under the stars. Luxuries like heated bathroom floors and premium linens set our place apart. brbrFor kids of all ages, we have toys, games, and DVDs. We also have child-friendly plates and utensils, two pack-n-plays (in addition to the crib), a high chair, infant tub, and more. If you need items for your kiddos, please coordinate with us - with either have it or can get it very easily to make your stay as enjoyable as possible. We have three kids ourselves and know what it's like to travel with them: what you need, what you want, and what you wish you had!brbrWhile we don't find ourselves in front of the TV often up here, we do have a TCL Roku TV with several apps, including HBO, Amazon Prime, and Netflix to stream your favorite shows. You can also mirror your laptop with Chromecast (directions provided). We aren't gamers, so we can't help you there. If you have any questions about connectivity, please ask!brbrPart of the charm our property is the privacy - we are out in the country, with a lot of acreage surrounding the house. Please be aware that this also means you might encounter wild animals on the property, from quail and owls to the occasional deer or coyote. If hearing these animals at night gives you pause, you might want to stay elsewhere. (Most people find this aspect of our place absolutely awesome.) brbrWe are officially within the Instacart delivery realm, which will save you a lot of time and effort! If you'd like us to order for you in advance of your arrival, please just let us know.brbrWe hope you enjoy Camp Bailey as much as we do!brbrPlease note: br- There is a 3-night minimum for all holidays.br- Pet guests require written approval and a pet fee.br- There are security cameras that observe the driveway and garage, as well as in locked areas not accessible to guests.

Family-Friendly Dry Creek Valley Retreat w/Amazing Views <15 Minutes To Square

Healdsburg, California, United States

Bed

Bath

Sleeps

$1257.95

Healdsburg Modern Wine Country Home is a 3BR/3.5BA two story luxury, smart home 3.5 miles from the Healdsburg Downtown square. This property is beautifully located less than ten minutes to Healdsburg and to Windsor where shopping, wine tasting, concerts and a multitude of year-round events are offered to visitors and locals alike. The features of this home and property are many, including smart devices, gourmet kitchen, luxurious living room with gas fireplace and oversized TV and comfy chairs and sofa. Outdoors are inground pool (heated May 1- October 31, extra charge outside these dates dependent upon season $300-500 start up and $100-150/day), hot tub, outdoor kitchen with lots of seating and tables, gardens, outdoor shower, views, and much more.brbrWalk in to a light-filled interior with open spaces. A roomy living area offers comfortable sofas and chairs surrounding a stone fireplace, and wall-mounted smart TV. An L-shaped desk is built in for a convenient work station, great for a zoom or video call. An open gourmet kitchen includes marble countertops, wooden cabinets, island with six-burner Wolf cooktop, Wolf ovens (great for Thanksgiving and holiday cooking), refrigerator, wine cooler and dishwasher. Dining for 8 + island seating. A handy laundry room with washer/dryer combo is also on the ground floor, and access to the garage.brbrUpstairs three bedrooms all with ensuite bathrooms are located. All have their own TV and bathroom, and a bench or chair for dressing, putting on shoes, etc. The primary has a private balcony overlooking the backyard and vineyards, and the two guest rooms share a second balcony. All beds have like-new mattresses and luxury bedding and comforters,. Extra pillows and blankets in the closet if needed. Two oversized chairs fold out to sleep two additional guests in living room.brbrThree BedroomsbrThree and a half bathroomsbrGas fireplacebrSmart home/TVbrWireless high speed internetbrVineyard viewsbrIn ground heated pool (May - October)brGas BBQbrFire tablebrHot tub

Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi

Healdsburg, California, United States

Bed

Bath

Sleeps

$411.83

Escape to a peaceful private retreat in Healdsburg wine country, surrounded by vineyards, rolling hills, and quiet countryside just minutes from wineries and downtown Healdsburg.brbrDesigned for relaxed wine country stays, this recently remodeled home offers vineyard views, a cozy fire pit, outdoor patio spaces, and the kind of peaceful setting guests remember long after their trip ends.brbrGuests consistently choose this home for its privacy, comfort, cleanliness, and convenient location close to Sonoma’s most celebrated wineries, scenic drives, and tasting rooms.brbrPerfect for couples, close friends traveling together, longer wine country getaways, and relaxing Sonoma escapes.brbrWake up to vineyard and hillside views in the heart of Sonoma Wine Country. Located in the Chalk Hill AVA, the home offers a rare balance of peaceful surroundings and convenient access to Healdsburg, Windsor, and nearby wine country attractions. Downtown Healdsburg Plaza is about 10 minutes away, while Napa Valley is also within easy reach for scenic day trips.brbrInside, guests enjoy bright and comfortable living spaces, a fully equipped kitchen, quality furnishings, high-speed WiFi, two full bathrooms, and thoughtful amenities designed to make longer stays easy and relaxing.brbrThe private outdoor spaces are one of the home’s favorite features. Enjoy morning coffee on the patio surrounded by vineyard views, afternoons exploring nearby wineries, and quiet evenings around the backyard fire pit with a glass of wine.brbrA complimentary bottle of local wine awaits you at check-in to help you settle in and begin your wine country getaway.brbrGuests also enjoy several exclusive local partnerships during their stay, including:br• 2-for-1 wine tastings at Alexander Valley Vineyards and Rodney Strong Vineyardsbr• Discounted small-group wine tours with Platypus Wine Toursbr• Preferred guest pricing at A Simple Touch Spa in downtown HealdsburgbrbrAdditional amenities include:br• Private EV chargerbr• Outdoor patio and balcony seatingbr• BBQ grillbr• Washer and dryerbr• Full kitchenbr• Pet-friendly accommodationsbr• Self check-in with keypadbrbrWhy guests love staying here:br• Peaceful vineyard setting with added privacybr• Recently remodeled interior with comfortable furnishingsbr• Convenient location near Healdsburg wineries and restaurantsbr• Cozy outdoor fire pit and relaxing patio spacesbr• Ideal for extended wine country staysbr• Consistently highly rated for cleanliness, comfort, and host communicationbrbrA favorite way to enjoy the property:brMorning coffee overlooking the vineyards, afternoon tastings at nearby wineries, dinner in downtown Healdsburg, and a relaxing evening by the fire pit under Sonoma wine country skies.brbrWhether you’re visiting for wine tasting, a relaxing getaway, a longer Sonoma stay, or simply a peaceful escape from the city, this Healdsburg retreat offers a warm and comfortable place to unwind and enjoy the best of wine country.

Private Vineyard Retreat • Wine Tasting Perks • Fire Pit

Healdsburg, California, United States

Bed

Bath

Sleeps

$1115.14

This newly remodeled vacation rental home is wonderfully located less than 8 minutes north of downtown Healdsburg. It is nestled on the rolling hills of Dry Creek Valley with views looking towards Alexander Valley. Recently refreshed with stylish furnishings, fixtures and lighting system, the home offers 2100 square foot with an open floor plan, three bedrooms and three bathrooms. You will enjoy abundant outdoor amenities, including a large seasonally heated, 10’ deep, swimming pool (winter months the solar system is disconnected and drained), Hot Springs spa as well as a covered arbor living/dining and cooking area. Adjacent to these amenities there is gas fire-pit with a relaxing seating arrangement. Retire to the warm interior of the home or continue your day or night with a trip to town. brbrCasa Chiquita’s landscaped property encourages guests to wander and let your day to day life slip away. There are several varieties of bountiful fruit trees, lush greenery and serene paths. You will find yourself easing into vacation mode in no time. Feel free to pick and enjoy any of fresh, ripe fruit or herbs that are in season on the property! brbr Now, let’s explore the spacious and inviting home. The large entry room offers a comfortable sofa, an original 1900’s solid oak antique icebox and provides a relaxing space to stop on your way in or for gearing up on your way out. Each bedroom is unique with soothing features. The master has a king bed with luxurious linens, a spacious closet, TV, full sized bath and shower. It also opens to a private deck with a dining table, additional seating and is just steps to the hot tub. The “pool” bedroom has a king bed and views of the pool. You can step out through the sliding door to take a swim or enjoy the fire pit and hot tub. This bedroom shares the bathroom with the “front room”. The front room overlooks the valley and offers a queen bed, leather loveseat sitting area and private entrance through the front of the home. It is down a short hall, tucked away from the other living areas of the home. The modern kitchen is abundantly supplied with everything you need to entertain. The 4-burner Wolf stove and well-appointed kitchen will tease your culinary creativities. The beautiful dining room is a perfect place to enjoy meals with your friends and family. Lastly, the warm and inviting living room provides plenty of space to relax while reading or watching TV. This home is set up with a Sonos sound system, Xfinity Wi-Fi and Lutron smart lighting controls. Sky lights, large windows and several sliding glass doors from every room allow for maximum natural lighting. Please make yourself at home at Casa Chiquita! brbrCasa Chiquita is perfect for 6 adults to enjoy all that Healdsburg and Sonoma wine country have to offer. We do not suggest this home for children under 10 as the pool is large, deep and uncovered. This home is also dog friendly, with an additional pet fee.brbr**Sonoma County Ordinances requirements are as follows:brbr• Maximum occupancy, not including children under 3, is 6br• Maximum number of vehicles allowed is 3br• Quiet hours must be observed between 09:00 p.m. and 7:00 a.m.br• Outdoor amplified sound is not allowedbr• The Transient Occupancy Tax Certificate number is 3513Nbr• No RV ParkingbrSmoking is strictly prohibited inside the housebrbrPlease 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!

Casa Chiquita-The Coziest in Town, 3 Bed, 3 full Bath, Spa & Pool

Healdsburg, California, United States

Bed

Bath

Sleeps

$1983.54

Healdsburg Wine Country Retreat with Heated Pool, Sauna & VineyardbrbrEscape to a private wine country retreat designed for connection, celebration, and slow, beautiful moments. Set on nearly an acre with your own vineyard and olive trees, this light-filled home blends elevated design with relaxed luxury, perfect for mornings with coffee on the deck, afternoons by the pool, and evenings under the stars.brbrWHY GUESTS LOVE ITbr- New heated pool (18’ x 40’, 5 ft deep) with Baja shelfbr- Private vineyard with 200 Zinfandel vinesbr- Cedar sauna, hot tub, and stone fire pitbr- Indoor-outdoor living with bifold glass doorsbr- Chef’s kitchen + dining for gathering br- Minutes to Healdsburg Plaza + top wineriesbrbrTHE SPACEbrLiving & DiningbrbrStep into a stunning, light-filled space designed for both relaxation and celebration. Gather around the Venetian plaster fireplace, sip champagne, or play vinyl on the McIntosh sound system. The open-concept chef’s kitchen features a handcrafted dining table for 8, a custom plaster range hood, and a chic bar for evening cocktails.brbrOutdoor LivingbrSeamless indoor-outdoor living unfolds as floor-to-ceiling bifold doors open to a sun-drenched wraparound deck. Host long, relaxed dinners under the vaulted redwood veranda or unwind after wine tasting in the hot tub or sauna.brbrOutdoor dining for 10br- Built-in gas grill + large kitchen islandbr- Six-person cedar sauna + hot tubbr- Stone fire pit for evening gatheringsbr- Heated pool with Baja shelfbr- Quiet nooks for morning coffee and sunrise viewsbrbrThe lush grounds feature a private vineyard, Mediterranean olive trees, and fruit trees—creating a true wine country setting.brbrBEDROOMS & BATHROOMSbrEach space is designed with comfort and elevated finishes in mind.brbrPrimary Suitebr- King bed with luxury linensbr- Private workspace + 55” TVbr- Spa-like bath with double vanity, Fireclay tile, heated Toto bidetbr- AquateX soaking tubbrbrLower King Suitebr- Private en suite bath with designer tile showerbr- Heated Toto bidetbr- Access to separate office/sitting roombrbrGuest Rooms (Upstairs)br1 King bedroom + 1 Queen bedroombr- Bright, airy spaces with ample storagebr- Lighted closetsbr- Shared bath with double vanity, soaking tub, and heated bidetbrbrGameroom & GymbrWhether you want to unwind or stay active, the home offers both.br- 75” HDTV with soundbarbr- Foosball + dartsbr- Gigabit WiFi for streaming and workbr- Stationary bike, dumbbells, and yoga matsbrbrLocationbrTucked in a quiet residential setting just minutes from:br- Healdsburg Plazabr- Dry Creek Valley wineriesbr- Alexander Valley vineyardsbr- World Class fine dining (Single Thread, Dry Creek Kitchen)brbrEnjoy world-class wine tasting, farm-to-table dining, and boutique shopping—all just a short drive away.brbrIndoor Comfortsbr-Fully stocked chef’s kitchen with premium appliancesbr-High-speed WiFibr-McIntosh receiver + record player + vinyl collectionbr-Washer and dryerbrbrGuest AccessbrGuests have exclusive access to the entire home and property, including private driveway parking.brbrImportant Notes (Please Read Before Booking)br- Maximum of 6 overnight guestsbr- No parties or large gatherings permittedbr- Quiet hours: 9 PM to 8 AM (monitored by outdoor cameras and decibel sensors)br- Pizza oven NOT available for guest use (county regulations)br- Property includes stairs, vineyard terrain, and an unfenced pool.brBest suited for adults or families with older childrenbrbrThis is a place to gather, slow down, and experience the best of Healdsburg, where thoughtful design, natural beauty, and wine country living come together effortlessly.

Luxury Healdsburg Retreat. Pool, Sauna, Hot Tub, Near Plaza, Tesla charger

Healdsburg, California, United States

Bed

Bath

Sleeps

$1968.58

Some places you visit. Others you sink into.brbrDry Creek Wonderland is 3+ secluded acres of Sonoma County at its most authentic—a sophisticated estate meets working honey farm nestled among the vineyards of Dry Creek Valley, offering the kind of privacy and beauty that inspired California’s original wine country dreamers.brbrHere, your morning begins with coffee on the covered loggia looking south over the lake, as the fog lifts to reveal rows of vines stretching toward the hills. Your afternoon might find you by the pool, glass of local rosé in hand, watching herons, hummingbirds, and hawks glide through the sky as the light shifts gold across the property. And evening That’s for gathering around the outdoor table or BBQ with friends and family, the olive tree scent of oak and honeysuckle in the air, as the stars emerge one by one over the valley.brbrbrSophistication relaxation meets laid back elegancebrbrDry Creek Wonderland is a private experience surrounded by vineyards and lakes, yet only minutes from the restaurants of downtown Healdsburg. You can soak in the sunsets, or relax by the pool, or the cedar hot tub. Dry Creek Wonderland is also an active apiary producing small-batch local honey—and you’re invited into that world. For guests who want to go deeper, we offer a private “hive dive” experience: an intimate, hands-on introduction to the art of beekeeping led by our on-site team. You’ll suit up, approach the hives, learn how honey is made, and leave with a jar of the very honey these bees produced. It’s the kind of experience you simply can’t find elsewhere—and one you’ll talk about long after you’ve returned home.brbr*Prefer to admire from afar That works too. The bees keep to their corner of the property, and you’re free to keep to the pool.*brbrbrDesigned for GatheringbrbrThe main residence seamlessly blends indoor comfort with the outdoor life that wine country demands. Four bedrooms and four bathrooms accommodate up to eight adult guests, and a six-bunk room allows little ones to rest or be active in their separate den. Each room is thoughtfully appointed, each bathroom private, so couples and friends can retreat and reconvene as the day unfolds. brbrThe heart of the home is the open kitchen and living area: a space built for long meals, unhurried conversations, musical enjoyment on the baby grand piano, and the kind of cooking that happens when you’ve just returned from the farmers market with too much produce and not enough plans. A generous island anchors the kitchen, while the living room opens directly to the terrace—because in wine country, the line between inside and outside should be as soft as the evening light. brbrbrThree Acres of Sonoma SolitudebrbrStep outside and the property unfolds: a heated pool and spa set against the quintessential oak and manzanita forest, with pond and vineyard views beyond; outdoor dining for the full group; a fire pit for evening gatherings; and garden, meadow, and fruit trees to explore at your leisure. Your breaths will deepen. Your nervous system will relax. brbrWhat you won’t find: neighbors within earshot, a crowded tasting room, or the sense that you’re on anyone else’s schedule. This is private wine country—the rolling hills, the honeybees, the silence broken only by birdsong—all yours for the length of your stay.brbrbrbrIn the Heart of Dry Creek ValleybrbrDry Creek Valley is where Sonoma insiders go when they want to escape Napa’s crowds without sacrificing the wine. The valley’s 60+ wineries produce some of California’s finest Zinfandels and Sauvignon Blancs, and many of the best tasting rooms are literally a five-minute drive from your door—or a leisurely bike ride through the vines.brbrThe charming town of Healdsburg, with its acclaimed restaurants, boutique shopping, and picture-perfect plaza, is just ten minutes away. Yet return to the property, and the modern world recedes. That’s the gift of Dry Creek: you’re close to everything, immersed in nothing but the land.brbrbrNearby:br- Dry Creek General Store and Single Thread Farm (2 min)br- 60+ Dry Creek Valley wineries (5-15 min)br- Healdsburg Plaza (10 min)br- Russian River beaches (20 min)br- Bodega Bay coast (45 min)br- San Francisco (75 min)brbrProperty Highlightsbr- 4 bedrooms, 4 full bathrooms (sleeps 8 adults)br- Heated pool (seasonal) and spa with vineyard viewsbr- Private honey farm with optional hive experiencebr- Chef’s kitchen with premium appliancesbr- Outdoor dining and BBQ for al fresco mealsbr- Baby Grand pianobrbr- Fire pit for evening gatheringsbr- High-speed WiFi throughout via Starlinkbr- EV charger availablebr- Private gymbrbr- Children’s play housebrbr - Pet-friendly (inquire for details)brbr**The Fine Print**br- Check-in: 4:00 PM | Check-out: 10:00 AMbr- Minimum stay varies by seasonbr- No smoking on propertybr- No events or parties beyond registered guestsbr- Rental Agreement will be sent immediately after booking to confirm reservationbrbrFarmstay Permit ZPE24-0192

Dry Creek Wonderland | Private Farm Estate in Wine Country

Healdsburg, California, United States

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