Vacation Rentals By Owner In Healdsburg, CA

$410.67

Wine Country Getaway - Healdsburg, Sonoma

Healdsburg, California, United States

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

3

Bed

2

Bath

6

Sleeps

$1028.05

/ Nightly

Private Vacation Home

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

Healdsburg, California, United States

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

Bed

Bath

Sleeps

$868

/ Nightly

Private Vacation Home

Healdsburg Vineyard Farmhouse with Game Barn

Healdsburg, California, United States

Summary:brbrWake to vineyard rows stretching outside your window while morning light filters through the farmhouse. This playful 3-bedroom retreat brings color and fun to wine country — ping pong in the converted barn, bocce ball on the lawn, sunset dinners on the covered deck. Room for 6 with a fully equipped kitchen perfect for farmers' market finds. Just 2 miles from Healdsburg Plaza and minutes from Aperture Cellars. Your wine country escape comes with all the games — and all the views.brbrbrbrThe Space:brbrSpend mornings under the porch as vineyard rows catch the first light, afternoons among Healdsburg Plaza's tasting rooms and SingleThread, and evenings on the patio with a glass from the day's barrel-room visits.brbrbrbrBoard games sit at hand around the wood-burning fireplace in the main family room; a second living area sets orange leather sofas beneath a painted-brick fireplace and exposed beams. A retro-style fridge and ample counter open the kitchen for prepping Healdsburg farmers' market hauls, flowing into dining inside and out on the covered deck. Out back, the converted barn is the wildcard — exposed trusses soar above a ping-pong table and built-in bookshelves, with a roll-up garage door that erases the line between indoors and out.brbrbrbrOUTDOOR LIVINGbrbrStep outside to discover multiple entertainment zones. The covered deck offers outdoor dining beneath bright orange metal chairs on a colorful striped rug. Challenge your group to bocce ball on the regulation court with its sandy surface and wooden rails. The converted barn steals the show — exposed ceiling beams and trusses soar above a blue ping-pong table, an orange sofa, and built-in bookshelves, with a roll-up garage door that opens to blur the line between indoors and out.brbrbrbrSLEEPING ARRANGEMENTSbrbrThree bedrooms sleep up to six guests. The primary bedroom offers a king bed with views overlooking the property. The second bedroom features a queen bed with white bedding. The third bedroom provides two twin beds with yellow accent pillows and large windows framing vineyard views.brbrbrbrPROPERTY AMENITIESbrbr-- Wood-burning fireplacebrbr-- Full kitchen with dishwasherbrbr-- Gas grillbrbr-- Ping-pong table in game barnbrbr-- Bocce ball courtbrbr-- EV charger (Tesla and CCS1 plugs)brbrbrbrGuest Access:brbrRoll up the barn door of the converted game room and let indoor-outdoor flow take over — ping-pong, exposed beams, vineyard views right outside. You've got the whole farmhouse, with a wood-burning fireplace, BBQ, outdoor dining, and an enclosed yard. Punch in the keypad code on arrival; free parking for up to five cars, with an EV charger (Tesla and CCS1 plugs) free for guest use.brbrbrbrThe Neighborhood:brbrYour farmhouse sits in the heart of Healdsburg wine country, surrounded by working vineyards just 2 miles from the historic Plaza. Walk next door (0.2 mi) to taste at Aperture Cellars, or explore nearby Christopher Creek Winery (0.5 mi) and Merriam Vineyards (0.6 mi). The famous Foppiano Vineyards, family-owned since 1896, is just 0.6 miles away. When hunger strikes, Healdsburger serves gourmet burgers 1.8 miles away, while TISZA BISTRO (2.1 mi) offers European comfort food with schnitzel and spätzle. The charming Healdsburg Plaza (2.3 mi) anchors downtown with tasting rooms, galleries, and the Saturday farmers' market. For outdoor fun, Healdsburg Veterans Memorial Beach on the Russian River is just 1.5 miles for summer swimming and kayaking. Stock up on provisions at Estrella's Market & Taqueria (1.8 mi) or grab morning coffee at Ana's Cafe & Espresso (1.8 mi).brbrbrbrGetting Around:brbrHealdsburg is about 75 minutes from San Francisco via US-101 North — a straight, scenic drive into the heart of Sonoma wine country. You'll find ample free parking for up to 5 vehicles on the property, including EV charging. A car is the easiest way to take in the three valleys that meet here — Dry Creek, Alexander, and Russian River. For tasting days, plan a designated driver or book a rideshare ahead — it makes the whole day easier.brbrbrbrOther Things to Note:brbrThe home stays naturally cool thanks to cross-ventilation and shade trees, with air conditioning available for warmer days. Internet runs at 32 mb/s download speed, perfect for streaming. The primary renter must be 25 or older. Take advantage of the free EV charger — it works with both Tesla and CCS1 plugs. The converted barn game room is a special treat — roll up the garage door for indoor-outdoor ping pong matches. Don't miss sunset from the picnic tables by the bocce court. For the best farmers' market experience, visit Healdsburg Plaza on Saturday mornings starting in April. The property's one-acre setting means you'll enjoy privacy and quiet, with only the occasional tractor passing by during harvest season.

3

Bed

2

Bath

6

Sleeps

$220.62

/ Nightly

Private Vacation Home

Healdsburg Fitch Mountain Hot Tub Cottage

Healdsburg, California, United States

Summary:brbrSoak in the hot tub as Russian River views, vineyards, and rolling hills stretch toward Fitch Mountain itself — this 1940s Camp Rose cottage sleeps 4, with a semi-private community beach a half-mile downhill and Healdsburg Plaza tasting rooms two miles away.brbrbrbrThe Space:brbrSpend mornings with Nespresso on the deck as light catches the Russian River below, afternoons walking the half-mile down to Camp Rose's semi-private community beach or the public Del Rio Woods access a mile up the road, and evenings two miles away in downtown Healdsburg among the tasting rooms, vineyards, and restaurants around the Plaza.brbrbrbrSettle into the sectional in the sunny living room, where a stone hearth anchors the space and wall sconces throw warm light across the hardwood — a comfortable spot to plan tomorrow's run at Dry Creek Vineyard, Trentadue Winery, or Kendall-Jackson Wine Estate & Gardens.brbrbrbrCook in the vintage-style kitchen stocked with the essentials and a Nespresso maker, then linger at the dining table as a wall of windows pulls the hillside and river valley right to your plate. A pass-through window keeps the cook in the conversation, and the attached laundry room with washer/dryer makes longer stays easy — handy after a day at Armstrong Redwoods, Safari West, or the Luther Burbank Center for the Arts.brbrbrbrOUTDOOR LIVINGbrbrStep onto the expansive deck for your private hot tub overlooking the Russian River, vineyards, rolling hills, and Fitch Mountain itself. Pull up a chair at the outdoor dining table, sink into the comfortable sitting area furniture, or claim the hanging egg chair for an afternoon book — horizontal wood fencing and mature trees keep it all feeling private.brbrbrbrSLEEPING ARRANGEMENTSbrbr- Bedroom 1: King bed plus twin trundlebrbr- Bedroom 2: Twin bedbrbrSleeps 4 across 1 bathroom.brbrbrbrPROPERTY AMENITIESbrbr- Private hot tub with Russian River, vineyard, and Fitch Mountain viewsbrbr- Expansive deck with dining table, sitting area, and hanging egg chairbrbr- Full kitchen with Nespresso coffee makerbrbr- Washer and dryer in attached laundry roombrbr- One designated driveway parking spotbrbrbrbrThe home is subdivided into two units; your unit sits 5–6 steps down from the street-level driveway.brbrbrbrGuest Access:brbrSettle in by the floor-to-ceiling stone fireplace, then drift out to the deck and the private hot tub for the long valley view. You've got the whole cottage, with a hammock, outdoor dining, and vintage red-and-cream checkerboard floors in the kitchen. Grab the key from the lockbox; one designated drive spot, plus one usually-open on-street spot — neighborhood parking is tight.brbrbrbrThe Neighborhood:brbrPerched on the slopes of Fitch Mountain in the historic Camp Rose neighborhood, you're perfectly positioned to explore Healdsburg's wine country treasures. Walk just half a mile downhill to reach the semi-private Camp Rose beach access on the Russian River — exclusively for neighborhood residents. For more river fun, Del Rio Woods Regional Park (0.5 miles) offers public beach access and trails. The renowned Fitch Mountain Park & Open Space Preserve Trailhead (0.9 miles) provides hiking with panoramic valley views. Downtown Healdsburg's charming Plaza lies just 2 miles away, home to SingleThread Farm Restaurant (2.0 miles), Bravas Bar de Tapas (2.0 miles), and Valette (1.9 miles). Stock up on organic groceries at Shelton's Natural Foods Market (1.9 miles) or grab artisan sandwiches from Journeyman Meat Co. (2.0 miles). Wine tasting rooms line the Plaza, while the actual vineyards of Dry Creek Valley, Russian River Valley, and Alexander Valley fan out within a 15-minute drive.brbrbrbrGetting Around:brbrHealdsburg is about 75 minutes from San Francisco via US-101 North — a straight, scenic drive into the heart of Sonoma wine country. You have one designated parking space in the driveway, plus one on-street spot that's usually available. A car is the easiest way to take in the three valleys that meet here — Dry Creek, Alexander, and Russian River. For tasting days, plan a designated driver or book a rideshare ahead — it makes the whole day easier.brbrbrbrOther Things to Note:brbrThis 1940s cottage is part of the historic Camp Rose neighborhood, which means you'll have access to the semi-private Camp Rose river beach — a special perk only for residents! The home stays naturally cool thanks to cross-ventilation from its hillside perch, though air conditioning is available for warmer days. The vintage red and cream checkerboard flooring in the kitchen and laundry area is original to the home's 1940s character. The primary renter must be 21 or older. Your hot tub is private to your unit only, perfect for stargazing on clear mountain nights. The property is subdivided into two units; you'll have the lower unit with complete privacy and your own entrance. Those distinctive wall sconces and vintage details throughout are part of what makes this cottage so special — a true slice of old Healdsburg charm with modern comforts.

Bed

Bath

Sleeps

$611.12

/ Nightly

Private Vacation Home

Healdsburg Victorian Cottage on Vineyard Estate

Healdsburg, California, United States

Summary:brbrAn 1895 Victorian turret door opens to wine country magic at this Magnolia Ranch cottage. Sip morning coffee on the gingerbread-trimmed porch as vineyard rows stretch to distant mountains. This colorful 2-bedroom retreat sleeps 4 amid crown molding and original hardwood floors. Just 1.3 miles from Healdsburg Plaza's tasting rooms and SingleThread. Set on a working vineyard, you'll enjoy the authentic Alexander Valley wine country experience.brbrbrbrThe Space:brbrSpend mornings under the porch as vineyard rows catch the first light, afternoons among Healdsburg Plaza's tasting rooms and SingleThread, and evenings on the patio with a glass from the day's barrel-room visits.brbrbrbrTwo distinct sitting areas trade off — the main living room circles a painted-brick fireplace on Oriental rugs; a second room sets a tufted leather armchair beside its own brick fireplace. Crown molding, original hardwood floors, and built-in bookshelves tie the 1895 Victorian together. The modernized kitchen anchors with marble counters, a center island, a farmhouse sink, and a brand-new induction/convection oven — wine country cooking, period setting.brbrbrbrOUTDOOR LIVINGbrbrTwo furnished patios offer alfresco dining and relaxation against a backdrop of mountain and valley vistas. Fire up the gas grill for vineyard-view barbecues or spread a blanket beneath the grand walnut tree — this is wine country living at its most gracious.brbrbrbrSLEEPING ARRANGEMENTSbrbrThe queen bedroom is painted in warm terracotta tones with a white upholstered headboard and bay window nook. The king bedroom offers restful sleep amid period details and hardwood floors. Both rooms stay cool with central air conditioning. Two full bathrooms serve the home — one with white cabinetry, tan countertops, and a walk-in shower with gray tile; the second showcasing yellow walls, a pedestal sink, and white subway tile tub/shower combo. Total capacity: 4 guests.brbrbrbrPROPERTY AMENITIESbrbr-- Central air conditioningbrbr-- Full kitchen with new induction/convection ovenbrbr-- Washer and dryer in separate laundry roombrbr-- Gas grillbrbr-- Smart TVbrbr-- Parking for 2 vehiclesbrbrbrbrGuest Access:brbrStep onto the period porch of an authentic Victorian — octagonal turret, gingerbread trim — and look out over the surrounding vineyards. The whole farmhouse is yours, with outdoor dining and mountain, valley, and garden views from the windows. Punch in the keypad code on arrival; two smaller cars fit on the gravel pad, plus extra parking just before the house.brbrbrbrThe Neighborhood:brbrYour Victorian cottage sits in the heart of Healdsburg wine country, where three renowned wine regions converge. Just 1.3 miles away, the historic Healdsburg Plaza anchors downtown with its ring of tasting rooms, galleries, and farm-to-table restaurants. Stroll to nearby Tongue Dancer Wines (0.4 mi) or Arnot-Roberts (0.8 mi) for intimate tastings. When hunger strikes, Healdsburger (0.9 mi) serves gourmet burgers while The Parish Café (1.1 mi) offers California comfort food. For groceries, Lola's Market is just 0.9 miles away, with Safeway (1.2 mi) for larger hauls. Outdoor enthusiasts love Healdsburg Veterans Memorial Beach (1.0 mi) for summer swimming and Railroad Park (1.0 mi) for picnics. The Plaza hosts Saturday farmers' markets and summer concerts, while Michelin-starred SingleThread and casual Bravas tapas bar showcase the town's culinary range.brbrbrbrGetting Around:brbrHealdsburg is about 75 minutes from San Francisco via US-101 North — a straight, scenic drive into the heart of Sonoma wine country. Park in your private gravel spaces — two spots for smaller cars in front of the garage, with overflow parking near the house entrance. A car is the easiest way to take in the three valleys that meet here — Dry Creek, Alexander, and Russian River. For tasting days, plan a designated driver or book a rideshare ahead — it makes the whole day easier.brbrbrbrOther Things to Note:brbrThis 1895 Victorian cottage offers authentic wine country charm with some delightful quirks. The decorative fireplace adds period character but isn't operational for guest use. While the home lacks air conditioning common in newer builds, you'll find it stays naturally cool thanks to well-insulated walls that keep the interior cool. The separate laundry room with mint green paneling and vineyard views makes longer stays a breeze. The property's owners do not live on-site. The home's well-insulated walls keep it naturally cool during hot summer days. The cottage requires guests be 25 or older. Keep an eye out for local wildlife that occasionally wanders through this working vineyard property. For the best experience, book dinner reservations well in advance, especially at SingleThread (weeks ahead) or popular spots like Valette and Bravas.

2

Bed

2

Bath

4

Sleeps

$261.9

/ Nightly

Private Vacation Home

Healdsburg Fitch Mountain Cottage with River Valley Views

Healdsburg, California, United States

Summary:brbrThe Russian River Valley unfolds below your hillside perch at this cottage with panoramic views. Gather your crew of 12 in colorful, mid-century inspired spaces while kids play on the private swing set. Just 0.5 miles to Del Rio Woods Beach for river swimming and 1.9 miles to Healdsburg Plaza's tasting rooms and SingleThread. The rooftop deck puts you among the treetops — perfect for sunset toasts over the valley.brbrbrbrThe Space:brbrSpend mornings on the deck as light catches the willows along the river, afternoons paddling the Russian River or sipping at Aperture Cellars and Stuhlmuller, and evenings on the patio with a Healdsburg Plaza bottle and dinner from the grill.brbrbrbrA stone fireplace flanked by built-in shelving anchors the open living room, a sectional and leather lounge chair angled toward the valley. Exposed beams add cottage character overhead. The galley keeps the 1940s Camp Rose spirit alive with its yellow-and-grey checkerboard floor, a gas range, and a windowed breakfast nook for two. A separate dining room — orange accent wall, six-seat table — pulls the valley in through panoramic windows.brbrbrbrOUTDOOR LIVINGbrbrA narrow deck with white railings runs along the house, furnished with wooden lounge chairs sporting blue and white striped cushions, a red patio umbrella, and a geometric outdoor rug — your front-row seat to the valley panorama. The backyard is a playground paradise with a turquoise platform stage, red metal swing set with gymnastics rings and green swing, and turquoise metal chairs under mature trees. A ping-pong table rounds out the outdoor fun.brbrbrbrSLEEPING ARRANGEMENTSbrbrFive bedrooms sleep up to twelve guests. The master features a king bed and calming blue-green walls. A queen bedroom includes a wall-mounted TV and patterned area rug. One kids' room offers twin beds with a trundle and an orange accent wall. Another bedroom serves as a children's play space with a red slide, desk area, and daybed. The fifth bedroom provides a double bed plus two twins, one with a trundle.brbrbrbrPROPERTY AMENITIESbrbr-- Central air conditioningbrbr-- Full kitchen with gas range and dishwasherbrbr-- Stone fireplacebrbr-- Gas grillbrbr-- Ping-pong tablebrbr-- Deck and balconybrbrbrbrGuest Access:brbrStep out to a hillside deck where panoramic valley and mountain views fan out, then cook on retro-modern checkerboard kitchen floors back inside. You've got the whole cottage, with a stone fireplace, a ping-pong table, outdoor dining, and a family-friendly play yard. Grab the key from the lockbox; one designated drive spot, plus one usually-open on-street spot — neighborhood parking is tight.brbrbrbrThe Neighborhood:brbrYour Fitch Mountain perch puts you 0.5 miles from Del Rio Woods Regional Park with its Russian River swimming access and 0.9 miles from the Fitch Mountain Park trailhead for hillside hikes. Downtown Healdsburg's Plaza lies just 2.0 miles away, where you'll find SingleThread Farm (three Michelin stars), Bravas Bar de Tapas (1,731 reviews), and Valette for special occasions. Closer to home, grab provisions at Shelton's Natural Foods Market (1.9 miles) or coffee at the charming são francisco cafe (0.9 miles). Wine tasting starts 1.6 miles away at Hirsch Vineyards Tasting Room, Sapphire Hill Winery (1.7 miles), or Truett Hurst Winery (1.7 miles). For family fun, Villa Chanticleer Dog Park sits 0.9 miles away, and Healdsburg Veterans Memorial Beach offers summer swimming 1.6 miles down the road. The historic Healdsburg Plaza (2.0 miles) hosts Saturday farmers' markets and summer concerts.brbrbrbrGetting Around:brbrHealdsburg is about 75 minutes from San Francisco via US-101 North — a straight, scenic drive into the heart of Sonoma wine country. Park one vehicle in the driveway spot and another on the street (when available) — parking is strictly regulated in this neighborhood with only these two spots. A car is the easiest way to take in the three valleys that meet here — Dry Creek, Alexander, and Russian River. For tasting days, plan a designated driver or book a rideshare ahead — it makes the whole day easier.brbrbrbrOther Things to Note:brbrThe home stays naturally cool thanks to central air conditioning — a real treat during Healdsburg's warm summers. As one of the original 1940s Camp Rose cottages, you might notice charming quirks like the galley kitchen's cozy proportions or the home's vintage built-ins. The primary renter must be 21 or older. Your cottage is part of a subdivided property with another unit — a second guest party may be present on the property at the same time. You'll have complete privacy in your space. Parking is shared: the upstairs unit parks in the spot closest to the front yard, and the downstairs unit parks in the spot next to the lemon tree. The narrow deck offers spectacular views but keep an eye on little ones. Those valley vistas from nearly every window never get old — especially at sunset from the rooftop deck.

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Bath

Sleeps

$900.68

/ Nightly

Apartment

Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting

Healdsburg, California, United States

Your stay now includes a complimentary tasting for up to 4 guests at Ridge Vineyards which is within walking distance of the home!brbrEscape to the heart of Sonoma wine country at this luxurious 3-bedroom home in Healdsburg. Perfectly located for exploring the region`s acclaimed wineries, gourmet dining and breathtaking scenery. This spacious abode offers an unforgettable getaway for families and groups alike.brbrDiscover nearby attractions such as Healdsburg Plaza, the Russian River, hiking trails, and Dry Creek region wineries all within easy reach.brbrElegant Interiors: Enjoy refined comfort in our beautifully appointed living spaces, featuring stylish decor, premium furnishings, and ample natural light.brbrSleek Amenities: Prepare gourmet meals or simply enjoy our generously stocked coffee bar in a fully equipped kitchen with Wolf range, high-speed Wi-Fi, 5 flat-screen TVs, and plush bedding for a restful night`s sleep.brbrOutdoor Oasis: Step outside to the large patio with hot tub to soak up the California sun amidst scenic vineyard views, ideal for morning coffee or evening cocktails. Bocce ball court with vineyard views in backyard.brbrSpacious Layout: With three well-appointed bedrooms on the main level and a den/game room upstairs including a comfortable sleeper sofa, there`s plenty of room for everyone to relax and enjoy wine country living.brbrFully landscaped front yard with plentiful outdoor furnishings, corn hole and large lighted fully adjustable umbrella for shade. Be sure to use the fire pit as the sun sets when the west facing vineyards are illuminated. brbrThe backyard has a dining table that seats 10, bocce ball court and room for additional games such as plastic axe throwing. brbrNearby Attractions:brRidge Winery - .4 mibrMazzocco Winery – 1 mibrMauritson Wines – 2.4 mibrFrancis Ford Coppola Winery – 2.6 mibrTrentadue Winery – 3 mibrHealdsburg Plaza – 5 mi (10 minutes by car)brDowntown Geyserville – 5 mi (10 minutes by car)brbrTHINGS TO KNOW:brMust be 25 years of age to rent this propertybrLIC23-0097brQuiet Hours – 9pm-7ambrEvents and smoking are not permitted.brMaximum occupancy of 8 guests, not including children under 3

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Bath

Sleeps

$333.33

/ Nightly

Private Vacation Home

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

Healdsburg, California, United States

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

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$3376.3

/ Nightly

Private Vacation Home

Panorama Estate - Classic Wine Country Villa in Healdsburg

Healdsburg, California, United States

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

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$1309.68

/ Nightly

Private Vacation Home

Wine Country Gem | Pool | Hot tub | BBQ

Healdsburg, California, United States

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

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$991.76

/ Nightly

Private Vacation Home

Modern Sonoma Home w Private Pool & Vineyard Views

Healdsburg, California, United States

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

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$847.98

/ Nightly

Private Vacation Home

Healdsburg Plaza Gem-Hot Tub and Tastings Included

Healdsburg, California, United States

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

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Sleeps

$545.56

/ Nightly

Private Vacation Home

Redwood Riverfront - Hot Tub and Tastings Included

Healdsburg, California, United States

Summary:brbrEscape to Redwood River House along the Russian River, just 1.5 miles from Healdsburg Plaza. Enjoy riverfront views, hot tub, kayaks, modern comforts, and complimentary wine tastings!brbrbrbrThe Space:brbrEscape to Redwood River House, a beautifully updated 2-bedroom, 1-bathroom riverfront cottage along the Russian River, just 1.5 miles from downtown Healdsburg. Thoughtfully designed for couples, small families, or friends, this inviting Wine Country retreat pairs peaceful river views and mountain scenery with modern comforts and easy access to town.brbrbrbrHere, mornings begin with coffee on the deck, days unfold on the river or exploring nearby wineries, and evenings wind down in the hot tub.brbrbrbrThe Spacebrbrbrbr• Bright, open floor plan with wood floors and upscale furnishingsbrbr• Cozy living area with plush seating and lounge chairsbrbr• Dedicated workspace with high-speed Wi-Fibrbr• Fully equipped kitchen with modern appliances, pantry, and in-unit washer/dryerbrbr• Bedroom 1: Queen bed with luxury linensbrbr• Bedroom 2: Full bed with large closetbrbr• Additional sleeping: Queen-size air mattress availablebrbr• Full bathroom with walk in shower and fresh towelsbrbr• Central heat, new A/C, and backup generatorbrbrbrbrOutdoor Living & River Accessbrbrbrbr• Oversized deck overlooking the river and surrounding hillsbrbr• Two-person hot tub under the starsbrbr• BBQ grill and alfresco dining areabrbr• Relaxing outdoor seating with private river accessbrbr• Two kayaks available for guest use (guests must carry to shoreline)brbrbrbrAmenities & Conveniencesbrbrbrbr• High-speed Wi-Fibrbr• Dedicated workspacebrbr• Air conditioning and central heatbrbr• Drip coffee maker and French pressbrbr• Hair dryer, iron, and ironing boardbrbr• Self check-inbrbr• Two on-site parking spaces. Street parking is available but can be limited.brbr• Pet-friendlybrbrbrbrHospitality You Can Count OnbrbrbrbrBeyond the home itself, guests appreciate our attentive, responsive service. We’re dedicated to making your stay smooth, comfortable, and genuinely enjoyable—from booking through checkout.brbrbrbrExclusive Wine Country PerksbrbrbrbrAs our guest, enjoy free tastings for up to 6 guests at several exceptional local wineries:brbrMerriam Vineyards – Family-owned estate crafting elegant, Old World-inspired Bordeaux-style wines ($35 value per person)brbrOrsi Family Vineyards – Locally loved winery specializing in expressive, small-lot Italian varietals like Sangiovese and Schioppettino ($35 value per person)brbrStonemason Cellars – Small lot wines all sourced locally from Sonoma County grapes. Enjoy their Nibbles & Wine tasting experience ($35 value per person)brbrContact information will be sent in your booking confirmation. Guest of record must be present for all tastings. brbrbrbrAn unforgettable way to toast your Wine Country getaway!brbrbrbrLocation Highlightsbrbrbrbr• Just minutes to Healdsburg Plaza’s restaurants, shops, and tasting roomsbrbr• Surrounded by world-class wineries and farm-to-table diningbrbr• Close to redwood groves, hiking trails, and river activitiesbrbrbrbrPerfect for GroupsbrbrbrbrRedwood River Lodge, River View Lodge, Riverbend Retreat, and Heron House are all located on the same quiet street. Rent multiple homes for extra space, privacy, and shared riverside memories.brbrbrbrExperience a peaceful Wine Country escape at Redwood River House, where riverfront living, mountain views, and genuine hospitality come together for an unforgettable Sonoma getaway.brbrbrbrTOT #2290N | PERMIT #ZPE14-0505 | LICENSE #LIC23-0177brbrbrbrThe Neighborhood:brbrLocated in a quiet Residential Neighborhood on the same street as our River View Lodge, Riverbend Retreat, & Heron HousebrbrbrbrGetting Around:brbrUbers/Lyfts are available although wait time can vary.brbrbrbrOther Things to Note:brbrYou may also see this home listed as “Redwood Riverfront- Hot Tub and Tastings Included” on some booking sites.

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$715.13

/ Nightly

Private Vacation Home

River View Lodge - Hot Tub and Tastings Included

Healdsburg, California, United States

Summary:brbrEscape to River View Lodge along the Russian River, just 1.5 miles from Healdsburg Plaza. Enjoy riverfront views, hot tub, kayaks, spacious decks, and complimentary wine tastings!brbrbrbrThe Space:brbrTucked along the Russian River, just 1.5 miles from Healdsburg Plaza, River View Lodge is a private, peaceful retreat perfect for romantic getaways, family vacations, or remote work with a view. With stunning river frontage, a private dock, two kayaks, a hot tub, and an expansive deck over the water, this home offers an unforgettable Wine Country experience.brbrbrbrWhile this home impresses with its comfort and setting, it’s the personal touches that make your stay memorable. From a warm welcome to attentive support throughout your visit, we ensure every detail is taken care of.brbrbrbrLocal Winery Partnerships | Elevate Your Stay with Complimentary TastingsbrbrbrbrAs our guest, you’re invited to elevate your Wine Country stay with complimentary tastings at several small, locally owned wineries — (Guest of record must be present for all tastings)brbr• Merriam Vineyards – a family-owned estate crafting elegant, Old World–inspired Bordeaux-style wines; a $35 value per guest, complimentary for up to six guests.brbr• Orsi Family Vineyards – a locally loved winery specializing in expressive, small-lot Italian varietals like Sangiovese and Schioppettino; a $35 value per guest, complimentary for up to six guests.brbr• Stonemason Cellars – Small lot wines all sourced locally from Sonoma County grapes. Enjoy their Nibbles & Wine tasting experience; 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• Sleeps 6–8 guests comfortablybrbr• Primary Suite: California King + Queen sofa bed, river viewsbrbr• Guest Bedrooms: Two Queen beds with premium linensbrbr• 1.5 bathrooms, fully updated and stockedbrbr• Open-concept living area with floor-to-ceiling windows and river viewsbrbr• Fully equipped kitchen with modern appliances, cookware, and drip + stovetop espresso coffee optionsbrbr• Smart TV, board games, fast Wi-Fi, and comfortable seatingbrbr• Pack and Play and Highchair available for guest usebrbrbrbrOutdoor Featuresbrbr• Expansive riverfront deck with dining, lounge furniture, and unbeatable viewsbrbr• Private boat dock with 2 kayaks (seasonal; guests carry to/from dock)brbr• 4–5 person spa overlooking the riverbrbr• Gas BBQ grill for outdoor mealsbrbr• Ping pong table, beach chairs, and lower patio seatingbrbr• Generator backup for peace of mindbrbr• Washer & dryer available for stays 3+ nightsbrbrbrbrIdeal for Remote WorkbrbrHigh-speed Wi-Fi, indoor/outdoor workspaces, and calming river views make this a perfect spot to combine focus with relaxation.brbrbrbrYear-Round Enjoymentbrbr• Summer: Swim, kayak, or relax on the dockbrbr• Winter: Cozy up with central heat, hot tub soaks, and river viewsbrbr• All seasons: Romantic evenings, family meals, and quiet reflectionbrbrbrbrLocal Attractionsbrbr• Less than 5 minutes to Healdsburg Plaza: shops, fine dining, tasting roomsbrbr• Short drive to wineries, redwood hikes, golf, and Sonoma Coastbrbr• Walk or bike scenic Wine Country roadsbrbrbrbrPerfect for GroupsbrbrRiver View Lodge is steps away from Redwood River Lodge, Heron House, and Riverbend Retreat on the same quiet street. Rent multiple homes together for extra space, privacy, and shared riverside memories.brbrbrbrExtras & Notesbrbr• Max 3 vehiclesbrbr• 1 dog welcome with pet feebrbr• No parties/events (quiet hours 9 PM–7 AM)brbrbrbrExperience a peaceful, scenic Wine Country escape at River View Lodge — with riverfront views, modern amenities, and genuine hospitality for an unforgettable Sonoma getaway.brbrbrbrTOT# 2687N | Permit# ZPE16-0149 | LIC# LIC23-0078brbrbrbrGuest Access:brbrThe whole homebrbrbrbrThe Neighborhood:brbrLocated in a quiet Residential Neighborhood on the same street as our Riverbend Retreat, Redwood River House, & Heron HousebrbrbrbrGetting Around:brbrLyfts/Ubers are available although wait times can vary

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$2557.33

/ Nightly

Private Vacation Home

Modern, recently built home with stunning pool & beautiful views; 15 min to town

Healdsburg, California, United States

RECENT MODERN CONSTRUCTIONbrbrWelcome to our home in paradise. Less than 15 minutes to Healdsburg Square, but a world away. Recently constructed in 2020, our 5 bedroom house is located on 50 acres with vast views. You will have privacy and serenity, but not isolation. Work from home with a private office and printer.brbrYou will enjoy indoor/outdoor living at its finest at our home, designed to be sustainable and integrate with the natural surroundings, including plentiful redwoods and madrone trees. Perfect for two families to share, as two sets of bedrooms are on opposite sides of the house separated by the great room. 5 bathrooms, 4 indoor showers, and even an outdoor shower to rinse off after swimming.brbrEnjoy a walk in the woods, a nap in the hammock, morning coffee on the patio, lunch by the pool, yoga on the manicured lawn, or a glass of wine by the fire.brbrAmenities:br- Outdoor fire place and indoor fire placebr- Outdoor kitchen and built in BBQbr- Outdoor dining areas on patio and poolbr- Outdoor ping pong tablebr- Peloton bike available for usebr- High speed internetbr- Satellite TVbr- Sonos powered audiobr- 50' x 25' pool (solar heated May-Oct; May and October heating dependent on weather)br- In-pool spa (available year round)br- 50 amp 240 volt receptacle available for electric vehicle (need an adaptor that will fit a NEMA 14-50 outlet)brbrEast wing (1st floor):br- Master Bedroom: King bed and master bathroombr-Bedroom 2: Queen bedbr- Bedroom 3: 2 twin bunks (4 beds total)brbrWest wing (2nd floor):br- Bedroom 4: King bed, ensuite bathroombr- Bedroom 5: King bed, ensuite bathroombrbrA few caveats: the final 0.75 miles is on a dirt road, steep in places. Low clearance vehicles (e.g. sport cars) are not recommended; SUV/4WD recommended during rainy season. Cell service is spotty (AT&T is fine), but wifi is strong and calls/texts can be made by enabling wifi calling.brbr*STRICT NO PET POLICY. OUR DAUGHTER IS HIGHLY ALLERGIC*brbrSonoma County TOT Certificate No. 3758N

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$1165.94

/ Nightly

Private Vacation Home

The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included

Healdsburg, California, United States

Summary:brbrA luxurious villa with a private pool, hot tub, firepit, and complimentary tastings included!brbrbrbrThe Space:brbrWelcome to The Dragonfly, an exquisite oasis of luxury nestled in the heart of wine country. This sophisticated vacation rental offers an unforgettable experience, combining tranquility, elegance, and modern comfort. With its stunning outdoor area this property promises the ultimate retreat for adults seeking an escape from the hustle and bustle of everyday life.brbrbrbrAs you enter the estate you'll be enchanted by the tastefully designed interior, adorned with high-end furnishings and captivating artwork. The open-concept living area provides a seamless flow between the stylishly furnished living room, dining area, and fully equipped gourmet kitchen, creating an ideal space for sophisticated gatherings and private relaxation.brbrbrbrThe soothing breeze beckons you to unwind and indulge in leisurely afternoons under the warm sun. Surrounded by lush greenery and vineyard views, this private oasis offers a serene ambiance, perfect for lounging on the comfortable outdoor chairs with a glass of local wine in hand. The outdoor kids play area, bocce court and acreage will keep the kids running around and engaged!brbrbrbrFor those who appreciate the art of culinary excellence, the outdoor kitchen is a true delight. Featuring top-of-the-line appliances and ample counter space, it invites you to create gourmet masterpieces while savoring the picturesque surroundings. Dine al fresco under the shaded patio, immersing yourself in the beauty of wine country and enjoying the company of your friends and family.brbrbrbrAfter a day of exploration, rejuvenate your senses in the inviting backyard. The soothing bubbles and captivating views create an atmosphere of pure bliss, ideal for unwinding and reflecting on the day's adventures.brbrbrbrWe offer more than just a beautiful setting—we provide a personal touch. Guests appreciate our responsive, thoughtful approach that ensures every stay is smooth, supported, and relaxing.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 and reservations are required):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. (within walking distance of the villa)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!brbrbrbrBook your stay at this gorgeous homestead and experience a luxury vacation like no other. Whether you're seeking a romantic escape, a retreat with friends or a multi-family get together, this exceptional property offers everything you need to create cherished memories in wine country.brbrbrbrAdditional Info:brbr• House has 1 master en suite. The additional guest bedroom and a third room, both featuring King beds, share a Jack and Jill bathroom. (Third bed is in this third room, not in the living room as the breakdown suggests)brbr• House is equipped with a generator which will turn on automatically during power outages.brbr• Work out room has a Peloton bike, yoga mats, free weights, foam roller, & a split zone a/c / heater.brbr• Tesla Car Charger available for complementary use.brbr• Keurig and Drip Coffee maker as well as a bean grinder are available for guest use (Coffee not supplied).brbr• This is a whole house rental that is not shared with other guests or the owner. The pool house in the pictures is not part of the rental and will remain vacant and locked during your stay.brbr• Sonoma County quiet hours: 9PM-7AM. No amplified music at anytime per the Sonoma County ordinance thus this house does not have a bluetooth speaker.brbrbrbrbrbrPool heating is currently unavailable. Hot tub heating is included in the rental rate.brbrWith consistently warm weather, using the pool cover alone will raise the water temperature to the mid- to high-70s.brbrbrbrPermit#: TVR22-0045brbrTOT#: 4331NbrbrVR License#: LIC23-0104brbrbrbrThe Neighborhood:brbrLocated in a quiet residential area.brbrbrbrGetting Around:brbrUber/Lyft is available but wait times can vary.brbrbrbrOther Things to Note:brbrYou may also see this home listed as “Villa with Pool, Hot Tub and Tastings Included” on some booking sites.

2

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2

Bath

4

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$145.79

/ Nightly

Country House

Fully furnished ADU farmhouse in fabulous Healdsburg all utilities included

Healdsburg, California, United States

A perfect spot for someone seeking an extended vacation stay, traveling professionals or work from home- 30 day minimum stay. brWelcome home to your little piece of Wine Country paradise. Built in 2025 this fully furnished ADU offers everything you need for turn key luxury living. Situated on a serene 1-acre property off esteemed Dry Creek rd, it has vaulted ceilings and a bright and open floor plan with a living room, dining area, and a modern kitchen. The ensuite bedroom sits on the west side of the house and the den/work space sits on the east side with views of the flower farm and 2 miniature donkeys. A powder room and a laundry room with a stacked washer/dryer complete this elegant space. brAll utilities included-electric, gas, water and sewer and internet. Option for bi-weekly house cleaning and pets negotiable.

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$451.18

/ Nightly

Cottage

Mountain Cottage near Russian River, hiking & downtown, family and pet friendly

Healdsburg, California, United States

This cozy, rustic, cottage has 3 bedrooms, two queen beds and one double bed, sleeps 6, has 2 bathrooms. It is a 5-minute walk to the Russian River and a 10-minute car ride to downtown Healdsburg. The cottage has easy access to hiking trails behind the house, up Fitch mountain, and to the nearby dog park, at the Villa Chanticleer. There is an outside eating area, a deck, BBQ, and a fenced-in yard, excellent for pets and small children. Inside there is a washer and dryer, two flat screen tvs, and wifi availablity, gas fireplace, fenced-in yard. It is a relaxing place with few neighbors and many redwood trees. Once you arrive you feel like you are miles away, yet it is only a 10-minute car ride to downtown Healdsburg, with its elegant dining. boutique shopping, and wine tasting.

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$1181.98

/ Nightly

Apart-hotel

Three-Bedroom Hotel Suites in Downtown Healdsburg

Healdsburg, California, United States

We are a small, independent boutique hotel offering fully-furnished, high-end suites for your stay in Healdsburg. Each suite features three private bedrooms with en suite bathroom, a full-size gourmet kitchen, dining area, and a spacious living room. There are four suites in total - all located on the same level. The hotel suites at Two Thirty-Five offer all the comforts of home and are just steps away from Healdsburg's beautiful historic plaza. Whether you're traveling as a family or a group of friends, everyone can enjoy the relaxing atmosphere and still have a private space of their own.

Bed

Bath

Sleeps

$774.85

/ Nightly

Private Vacation Home

Healdsburg Plaza Charmer with Hot Tub!

Healdsburg, California, United States

Welcome to Clementine Cottage, your cozy wine country retreat, just off Healdsburg Plaza, and steps away from Sonoma County’s world class restaurants. This adorable 2 bedroom, 1 bath cottage offers the perfect blend of comfort, class and convenience. As you step inside, you’ll be greeted by a warm and inviting living space, complete with tasteful decor and plenty of natural light. And a pet-friendly home!brbrThe fully equipped kitchen boasts modern appliances, making meal preparation a breeze. Enjoy your morning coffee at the breakfast table, or dine al fresco on the patio surrounded by lush greenery. There you will also find a gas barbeque or a Big Green Egg for grilling, and a Tuscan built-in pizza oven. Clementine Cottage offers private Chef hire services, should you wish to use the wood-fired pizza oven. brbrThe two bedrooms are thoughtfully designed for optimal relaxation. The master bedroom features a comfortable queen-sized bed and vaulted ceilings, and a sitting area offering a private oasis after a day of exploring. It also features a dedicated workspace with a desk and chair for business travelers. The cozy second bedroom offers a queen-sized bed, and a sitting area. There is also a comfortable full-sized sleeper sofa in the living room. brbrAt dusk, relax in the Adirondack chairs out back, and enjoy a glass of wine next to the warm fire pit. If a soak in a two-person hot tub is what you desire, Clementine Cottage has that too!brbrLocated within walking distance to Healdsburg Plaza, you’ll have easy access to award-winning restaurants, charming boutiques, and renowned tasting rooms showcasing the region’s finest wines. Take a leisurely stroll through the picturesque historic streets or embark on a wine tasting adventure just steps from your doorstep. Take a short drive to the river for a day of fun on the water at Veteran’s Memorial Beach – kayak and stand-up paddle board rental is available. Clementine Cottage is 40 minutes from Bodega Bay, and other Sonoma County attractions, 40 minutes from Napa Valley, and 90 minutes from San Francisco. Whether you’re seeking a romantic getaway or a memorable vacation with loved ones, this delightful cottage provides the perfect base for experiencing all that Healdsburg and Northern California has to offer.brbrLevel 2 Non-Tesla EV charging is available onsite. If you have a Tesla, you will need to bring an adaptor. brbrThere is a separate mid-term rental behind Clementine Cottage that is available for 30+ day rentals. Access is through the yard for The Cottage, so you may see the occasional tenant walking through, however, the patio/yard/deck use is for Clementine Cottage only.brbrA security deposit hold, ID verification, and signed renter agreement will be required following booking.

2

Bed

1

Bath

6

Sleeps

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