Healdsburg Vacation Rentals: A Visitors Guide

Welcome to our visitors guide about Healdsburg vacation rentals. Here you can find information to help plan your California wine country vacation, including gorgeous Healdsburg homes for rent, Healdsburg attractions, travel tips, and important details about the area.

TheWineStay.com also offers curated vacation experiences including personalized boutique wine tours and wine tastings, private dinners by 5-star chefs, and local guides for outdoor adventures. Read on to discover the possibilities.

Healdsburg Vacation Homes For Rent

Browse a selection of beautiful vacation homes available for rent in Healdsburg, California. Choose from private rural retreats among the hills to charming & elegant homes near downtown Healdsburg. These wine country homes each offer something unique for travelers.

Art & Wine Estate

Art & Wine Healdsburg vaction Rental

This 1930s, Tudor-style vacation rental includes inlaid oak floors, tall multi-paned windows and wrought iron handrails blended with modern upgrades and whimsical art. Enjoy private garden paths and a pool outside.

  • 4 Bedrooms
  • 3 Bathrooms
  • Max Capacity: 8 Guests
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At Home In Downtown Healdsburg

Downtown Healdsburg Vacation Rental Home

This historic farmhouse vacation rental near downtown Healdsburg offers a balance of modern amenities and rustic characteristics — original redwood flooring, vintage brass fixtures, 2 fireplaces with brick chimneys, a piano, and a dining room that seats 8.

  • 4 Bedrooms
  • 2 Bathrooms
  • Max Capacity: 10 Guests
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Private Wine Country Retreat

Private Wine Country Retreat For Rent in Healdsburg

Set atop rolling hills among the vineyards, this vacation rental includes a fully equipped outdoor kitchen with a gas grill, a Mugnaini wood-fired pizza oven, and a fire pit. The open, airy interior is bathed in natural light with tastefully designed rooms, a chef’s kitchen, and plenty of space.

  • 4 Bedrooms
  • 3.5 Bathrooms
  • Max Capacity: 8 Guests
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Upscale Home Among The Vineyards

Upscale Home Among Vineyards For Rent In Healdsburg

This Healdsburg Wine Country vacation rental boasts a first-rate entertainment system, super comfortable bedrooms & open living area. Outside, enjoy the spacious deck that overlooks acres of Sauvignon Blanc and Zinfandel vineyards.

  • 2 Bedrooms
  • 2 Bathrooms
  • Max Capacity: 4 Guests
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How To Choose The Right Wine Country Vacation Rental

Interior View of Art & Wine Estate For Rent

An amazing wine country vacation starts with choosing the perfect place to stay. While hotel rooms may be the better choice for some, nothing beats the privacy and convenience of your own vacation rental. Renting a home is perfect for larger groups or families with children. Space to spread out, privacy, an at-home feel, and cost savings make Healdsburg vacation rentals an attractive option.

Vacation home rentals are more popular than ever, and choosing the right place can make all the difference. Consider the following points when choosing a home to rent in Healdsburg.


Make a list of the most important amenities. Does your group want to BBQ outside? Do you need a pool or spa? Do you need a place for the kids to play while allowing the adults a bit of privacy? Be sure your rental home of choice isn't missing any essentials.


Do you want to be closer to the action in town, or are you looking for tranquility in a quiet setting? Is the vacation home near the attractions and points of interest that intrigue you most?

Property Photos

Look for a vacation rental with plenty of photos. Scrutinize the details to look for signs of cleanliness and upkeep. Explore what kind of views you'll have both indoors and out. If the photos of the property are in short supply or seem incomplete, this could be a red flag.


Check for consistent comments and take heed of criticisms. Make note of what people say about the property, atmosphere, amenities, and the owner or rental manager.


Some vacation rental agencies offer concierge services. These include shopping, transportation, private chefs and sommeliers, spa services, and more. The Wine Stay can arrange for a private yoga session, professional massage, or customized wine pairing – all in the comfort of your vacation rental.

Hotel or Rental Home - Which Is Right for You?

Can't decide if you should stay at a hotel or rent a home? Read our blog post "Vacation Home Rental or Hotel — Which Is Better for You?" to compare the advantages of these two types of accommodations.

Healdsburg Travel Tips

To help you create an amazing vacation experience in Healdsburg, here are some travel tips to keep in mind.

Local Weather

While enjoying your Healdsburg vacation rental, you can expect cool, wet winters and warm to hot, dry summers. Monthly average temperatures for Healdsburg are listed below in degrees Fahrenheit.


  • Highs: upper 50s
  • Lows: lower 40s


  • Highs: lower 60s
  • Lows: lower 40s


  • Highs: mid 60s
  • Lows: mid 40s


  • Highs: lower 70s
  • Lows: mid 40s


  • Highs: lower 80s
  • Lows: lower 50s


  • Highs: mid 80s
  • Lows: mid 50s


  • Highs: lower 90s
  • Lows: mid 50s


  • Highs: upper 80s
  • Lows: mid 50s


  • Highs: mid 80s
  • Lows: mid 50s


  • Highs: upper 70s
  • Lows: upper 40s


  • Highs: mid 60s
  • Lows: lower 40s


  • Highs: upper 50s
  • Lows: upper 30s

Local Transportation

Healdsburg may be a small town but there are plenty of transportation options available to help make the most of your wine country vacation.

By Car

Many visitors to Healdsburg get around using their own vehicle. Cars can also be rented from Enterprise Rent-A-Car in Healdsburg and several other rental car agencies in the nearby town of Santa Rosa.

Enterprise Rent-A-Car
18 Healdsburg Ave
Healdsburg, CA 95448
+1 707-431-9390

Personal Driver

We can arrange for a personal driver to pick you up at the airport or drive you around wine country, whatever makes your experience with The Wine Stay comfortable and easy.

Ride Sharing

While vacationing in Healdsburg, visitors can use the popular ride sharing apps Uber & Lyft to get around town.

Healdsburg Shuttle (Free)

The city offers a free shuttle bus to get around town while enjoying your Healdsburg vacation home. Visitors can hop on and off the bus as needed, with stops near the Safeway Shopping Center, Healdsburg Plaza, CVS store, Alliance Medical Center and many other locations.

The shuttle bus runs from Monday through Saturday from approximately 9am to 4pm. Visit the City of Healdsburg Public Buses page for exact times and route.

Things To Do In Healdsburg

Restaurants & Dining

Healdsburg is a foodies paradise with an excellent selection of cafes and restaurants. Below is a list of just a few of our favorite places to eat and drink while enjoying your Healdsburg vacation rental.


Costeaux French Bakery
17 Healdsburg Ave
Healdsburg, CA 95448
+1 707-433-1913

For the best breakfast in town, head to the plaza downtown. Try their eggs benedict if you want a satisfying meal. Everything is baked on-site, so their breads and pastries are always fresh. The service is great here, too.

Downtown Bakery & Creamery
308 Center St
Healdsburg, CA 95448
+1 707-431-2719

Although this place may not look like much, their baked goods are fantastic. Don’t be put off by the locals on the benches out front; we’re a friendly bunch who know a good value when we see it.

Flying Goat Coffee
17 Healdsburg Ave
Healdsburg, CA 95448
+1 707-433-9081

This established coffee house is the place to go for a real cup of coffee and is located right off the downtown plaza. It’s a hangout for locals and visitors alike – a place you can sit for a while with your laptop or newspaper. This spot is also good for people-watching in Healdsburg.


Bravas Bar De Tapas
420 Center St
Healdsburg, CA 95448
+1 707-433-7700

Bravas has a friendly and casual atmosphere. It’s fun and festive. Kick back with a drink at the bar and order some appetizers. Their paella is out of this world!

Campo Fina
330 Healdsburg Ave
Healdsburg, CA 95448
+1 707-395-4640

Campo Fina is a casual Italian restaurant that is right for the whole family. Enjoy well-priced, good quality cooking. There's also an outside dining area in the back.

Willi’s Seafood & Raw Bar
403 Healdsburg Ave
Healdsburg, CA 95448
+1 707-433-9191

This is the go-to place for top-notch seafood in Healdsburg. The atmosphere is casual yet sophisticated. The portions are tapas-sized and it’s a little pricey, but well worth it for the amazing taste experience.


Baci Cafe & Wine Bar
336 Healdsburg Ave
Healdsburg, CA 95448
+1 707-433-8111

Baci has a fun atmosphere, good food and really friendly service. It’s enjoyable Italian food for the whole family, and the owners often come and visit guests at the table to ensure a great experience.

231 Center St
Healdsburg, CA 95448
+1 707-431-0100

Be sure to do the wine pairing at Barndiva. They serve generous portions of wine perfectly matched to exquisite bites. It’s a little pricey, but the food is phenomenal and the service is A+. Reserve your table a few weeks in advance.

Madrona Manor
1001 Westside Rd
Healdsburg, CA 95448
+1 707-433-4231

If you want to share a romantic dinner in an historic landmark, this is the place to go in Healdsburg. They do a nice Sunday brunch, too.

Wine Tours

A wine country vacation isn't complete without sampling some of the finest wines in the country. Below are a few choices for wine tours in Healdsburg.

The Wine Stay
1083 Vine St, #723
Healdsburg, CA 95448
+1 707-890-0852

For our guests who like the idea of a customized wine tasting, take advantage of The Wine Stay’s in-house sommelier. Want to focus on a certain varietal, organic wines, or family-owned wineries? Our wine expert knows the region and its winemakers and can curate a wine tour just for you.

Wine Country Journeys
Sonoma County, CA
+1 707-478-7317

Tour the northern Sonoma wine regions of Dry Creek Valley, Alexander Valley, and Russian River Valley with these small group tours. They'll even pick you up at your location with exclusive door-to-door service. No driving required.

Winery Maps

Healdsburg deserves its reputation as the heart of wine country. With hundreds of wineries, there’s plenty of choice for wine tasting. Take a look at these maps to help you plan out your wine tour through the rolling hills of Sonoma Country.

Alexander Valley Map
Russian River Valley Map
Dry Creek Valley Map
Healdsburg Map

Outdoor Activities

A Healdsburg vacation rental is a great choice for outdoor enthusiasts. From biking and kayaking to golfing and nature walks, Healdsburg offers a wealth of options. Here are just a few local outdoor activities in Healdsburg.

Wine Country Bikes
61 Front St
Healdsburg, CA 95448
+1 707-473-0610

Rent a variety of different bikes and strike out on your own adventure, or take a one-day guided bike tour of Dry Creek Valley.

Tayman Park Golf Course
927 S Fitch Mountain Rd
Healdsburg, CA 95448
+1 707-433-4275

This 70 par, PGS regulation 9-hole golf course overlooks the beautiful Dry Creek Valley. Play the course twice using different tees for an 18-hole experience.

River's Edge Kayak and Canoe Trips
13840 Healdsburg Ave
Healdsburg, CA 95448
+1 707-433-7247

River's Edge offers complete and hassle-free river excursions along the Upper Russian River. Trips are self-guided, but guides are available with advance notice.

Local Laws & Regulations in Healdsburg

Nothing can ruin a perfect vacation like running afoul of local laws. Here are a few tips to keep you informed while enjoying your Healdsburg vacation rental.

Legal Drinking Age

The legal drinking age in Healdsburg is 21. Guests must also be 21 years of age or older to participate in wine tastings. Some wineries are more family friendly than others and may allow underage children to enter the winery but not participate in tastings. Contact the winery or your concierge for more details.

Alcohol Sales & Consumption

The legal age to purchase alcohol in Healdsburg is 21. According to California state law, alcohol may be purchased between the hours of 6:00am to 2:00am any day of the week.

Noise Regulations

Sonoma County regulates the acceptable amount of noise on vacation rental properties to ensure a pleasant experience for residents and guests.

  • Quiet hours must be observed between 10:00pm and 7:00am.
  • Outdoor amplified sound is not allowed at any time.
  • Continual nuisance barking from unattended pets is prohibited.

History of Healdsburg

Healdsburg, California in 1872

Healdsburg is located in Sonoma County, in California's Wine Country. The area is rich in history and is home to three of the top wineries in the United States.

During the California gold rush of 1849, many people discovered a preference for farming over the challenges of gold mining. One such man, an Ohio businessman named Harold Heald, left mining and built a cabin in the area of what is now Healdsburg. He later built a small general store and post office around which a small settlement was established. Healdsburg was officially founded in 1857 when Heald purchased more property and hired a surveyor to plan out a central plaza and home lots. The town was incorporated in 1867.

With the arrival of the railroad in the early 1870s, Healdsburg became prosperous in agriculture as well as tourism thanks to the recreational opportunities of the Russian River. The local agriculture included grapes, and the area's wine industry began.

With the passage of the Volstead Act and Prohibition in 1919, Healdsburg's growing wine industry fell apart. Throughout the 1920s, most of the vineyards in Healdsburg were replaced with fruit orchards. Prunes became the most important source of revenue for the area. Things stayed this way up until the 1970s when many of the orchards were replaced with vineyards. Wine remains the top agricultural industry in Healdsburg to this day.

To learn more about Healdsburg, read our blog and visit these other great resources online: