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 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, private sommeliers or 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 a convenient choice for some, nothing beats the privacy and spaciousness of a gorgeous rental home. Renting a home is perfect for larger groups or anyone looking for more privacy and intimacy during their wine country vacation.

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 & sommeliers, spa services and more.

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


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


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


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


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


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


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


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


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


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


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


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


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

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.