Wine & Dine Downtown Healdsburg | Walk Everywhere

Rectangular outdoor swimming pool surrounded by a concrete patio, pergolas, and a pool house under a blue sky.

Open living area with a large blue sectional sofa, wooden coffee table, patterned area rug, and hardwood floors, leading to a dining area and kitchen.

Covered outdoor porch with cushioned wicker seating, a freestanding barbecue grill, and railings overlooking neighboring buildings.

Bedroom with carpeted flooring, a bed with light blue bedding, an upholstered armchair, and an exterior door.

Living room with a large sectional sofa, lit fireplace, television on a wooden media console, and an open doorway leading to a dining area.

Dining area featuring a glass-top table with six tufted upholstered chairs over a colorful patterned rug, lit by a linear pendant chandelier.

Exterior view of a home with a two-car garage, front entrance door, and paved driveway on a sunny day.

Spacious bedroom with carpeted floors, a bed made with blue bedding, a television on a wooden dresser, a desk with a computer, and striped armchair.

Close-up of a kitchen countertop with a coffee maker, mug tree, small wine cooler, and built-in microwave.

A home office setup featuring a corner wooden desk with two monitors and a printer next to a large dresser with a flat-screen TV.

Bedroom with a bed made in blue linens, matching nightstands with lamps, an armchair by a window, and a wooden chest at the foot of the bed.

Bedroom with a tufted headboard, nightstand with flowers, a window with a small desk, and a television on a dresser.

Bedroom featuring a tufted upholstered bed, nightstand with lamp, decorative round mirror, and carpeted floor.

Bedroom with a bed, wooden dresser holding a flat-screen TV, and an open doorway leading to an en-suite bathroom.

Bathroom with marble-pattern vanity counter and mirror reflecting a tiled shower, opening into an adjacent bedroom.

A bathtub and shower combination surrounded by white chevron and subway wall tile with a glass partition.

A kitchen with white cabinets, stainless steel refrigerator, dark countertops, and a breakfast bar with two barstools.

Kitchen with dark countertops, white cabinetry, a stainless steel range, and an under-mount sink looking into the living room.

Kitchen counter and stainless steel gas range with pendant lights and a view into the adjoining dining or living room.

Kitchen featuring white shaker cabinets, dark countertops, a stainless steel refrigerator, and breakfast bar seating.

Dining room with a glass-topped table, tufted upholstered chairs, hanging light fixture, and view into the adjacent living room.

Bathroom with yellow walls, a vanity with a drop-in sink, a toilet, and a glass-enclosed shower tub combo tiled in white.

Exterior view of a two-story home with a white picket fence, covered front porch, and upper-level balcony.

Exterior steps leading to a covered porch with a loveseat bench and a barbecue grill.

Paved residential alley or shared driveway flanked by cottage-style homes and garages under a blue sky.

An outdoor swimming pool surrounded by a concrete patio, wooden pergola, and privacy fencing beneath a partly cloudy sky.

A carpeted staircase leading to an upper floor, viewed from a hallway with wood-look flooring and framed art on the walls.

Living room with hardwood floors, a dark sectional sofa, a fireplace with dark marble surround, and built-in bookshelves.

Living room with a dark sectional sofa, lit fireplace, television, desk, and hardwood floors.

A small round high-top table with two leather-cushioned bar stools placed against a half-wall beneath wine-themed wall art.

A dedicated workstation nook with a wooden desk, chair, printer, small window, and a tall bookshelf filled with board games.

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House in Healdsburg, California

4 guests • 2 bedrooms • 2 beds • 2 full baths

5.00

• 7 reviews

Welcome to your charming downtown Healdsburg retreat. A stylish and comfortable getaway just one block from world-class wine tasting rooms and three blocks from the historic Town Plaza. This modern 2-bedroom, 2-bath home offers over 1,500 square feet of thoughtfully designed living space, perfectly blending comfort, convenience, and Sonoma wine country elegance. This home is perfect for your 30+ day getaway (possible discounts for stays outside of 30 days). Inside, an open-concept living area invites you to unwind with a plush sectional, a cozy gas fireplace, and a 60-inch Smart HDTV with premium sound. The fully equipped kitchen features granite countertops, stainless steel appliances, and all the essentials for cooking and entertaining. A writing desk and pub table provide space for casual dining or remote work between wine country adventures. Upstairs, vaulted ceilings and natural light create an airy feel in the two spacious bedrooms, each with a queen bed and high-quality linens. The elegant master bath includes a soaking tub for ultimate relaxation after a day exploring Healdsburg’s tasting rooms and boutiques. Step outside to enjoy two private decks; ideal for morning coffee or an evening glass of wine and take advantage of the gas BBQ for home grilled meals. The community offers access to a serene saltwater pool, gas BBQ area, and bocce court, perfect for laid back afternoons in the sun. Whether you’re here for the Tuesday and Saturday Farmers Markets, summer concerts on the plaza, or simply to unwind in one of California’s most celebrated wine regions, this downtown Healdsburg home places you right in the heart of it all. Sleeping Arrangements: Bedroom 1: Queen Bed Bedroom 2: Queen Bed

What this place offers

Crib
Bathtub
Shower
Hair dryer
Board games
Books
Children's books
Toys
Indoor fireplace
Desk

Where you'll sleep

Bedroom 1

1 queen

Bedroom 2

1 queen

Healdsburg, CA, USA

About the neighborhood

Set in the heart of downtown Healdsburg, this home offers the perfect balance of small-town charm and upscale Wine Country living. Just three blocks from the historic Healdsburg Plaza, you’ll be surrounded by tasting rooms, boutique shops, award-winning restaurants, and weekly farmers markets—all just a short stroll away. This vibrant neighborhood is one of the most desirable areas in Sonoma County, known for its walkability, friendly community, and sophisticated yet relaxed atmosphere. Guests can start their morning with coffee from a local café, spend the afternoon wine tasting or exploring nearby galleries, and end the day with an unforgettable meal at one of Healdsburg’s Michelin-rated restaurants—all without ever needing to drive. For those looking to venture out, scenic drives lead to the rolling vineyards of Dry Creek Valley, Alexander Valley, and Russian River Valley—all within 10–15 minutes. Outdoor enthusiasts will appreciate the nearby hiking and cycling routes through vineyard-lined backroads, while the Russian River offers kayaking and paddleboarding just a short drive away. Entertainment & Activities: • Healdsburg Plaza – 0.3 mi • Raven Performing Arts Theater – 0.3 mi • Healdsburg Museum & Historical Society – 0.4 mi • Hand Fan Museum – 0.4 mi • Tayman Park Golf Course – 1.3 mi • Francis Ford Coppola Winery Movie Gallery – 10.0 mi • Luther Burbank Center for the Arts (Santa Rosa) – 15.0 mi Wine Tasting: • Williamson Wines – 0.2 mi • Banshee Wines – 0.3 mi • Portalupi Winery – 0.3 mi • Ferrari-Carano Vineyards – 9.0 mi • Jordan Vineyard & Winery – 6.0 mi • Dry Creek Vineyard – 6.5 mi • J Vineyards & Winery – 7.0 mi • Rodney Strong Vineyards – 3.5 mi Dining & Culinary Experiences: • Valette – 0.4 mi • Chalkboard – 0.3 mi • The Matheson – 0.3 mi • Costeaux French Bakery – 0.2 mi • Bravas Bar de Tapas – 0.5 mi • Barndiva – 0.3 mi Outdoor Adventures: • Healdsburg Ridge Open Space Preserve – 2.8 mi • Riverfront Regional Park – 5.0 mi • Lake Sonoma Recreation Area – 12.0 mi • Armstrong Redwoods State Natural Reserve – 17.0 mi • Sonoma Zipline Adventures – 20.0 mi Local Towns for Shopping & Day Trips: • Geyserville – 8.0 mi • Windsor – 10.0 mi • Santa Rosa – 16.0 mi • Cloverdale – 17.0 mi • Sebastopol – 19.0 mi Nearest Airports: • Charles M. Schulz–Sonoma County Airport (STS) – 10 mi • Oakland International Airport (OAK) – 78 mi • San Francisco International Airport (SFO) – 83 mi

Getting around

Staying in downtown Healdsburg makes getting around easy and convenient. Most of the town’s best restaurants, tasting rooms, and shops are just a short stroll or bike ride away, so you can leave the car parked and explore on foot. For longer outings—like visits to nearby wineries in Dry Creek or Alexander Valley—driving is the easiest option, though local rideshare services such as Uber and Lyft are available in the area (wait times can vary slightly during peak wine-tasting hours). Bike rentals, private drivers, and wine-tour shuttles are also easy to arrange through several local companies.

Things to know

House rules

Check-in after 4:00 PM
Check-out before 10:00 AM
4 guests maximum

Safety & property

Fire extinguisher
First aid kit
Carbon monoxide alarm installed

Cancellation policy

Add your trip dates to get the cancellation details for your stay.

This property is managed through Fairly. It is also available on sites like Airbnb and Vrbo, but the lowest price is always at Fairly.com. Avoid service fees by booking direct.

For homeowners

Company

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