Healdsburg vacation rentals

We found 583 vacation rentals — enter your dates for availability

Discover a selection of 139 homes, 11 apartments, and other vacation rentals in Healdsburg that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the best amenities for hanging out with the people that matter most, which might include WiFi and a pool. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Healdsburg

Showing deals for:May 22 - May 29

Image gallery for Santini Farmhouse with Tastings Included

Miscellaneous
10 out of 10, Exceptional, (53 reviews)
Exceptional
(53 reviews)

Santini Farmhouse with Tastings Included

Healdsburg

8% off
Price is $696
$4,871 for 7 nights
All fees included
Santini Farmhouse with Tastings Included

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Find out more about Healdsburg

Why visit Healdsburg

  • Charming Outdoor Spaces: Healdsburg boasts beautiful parks, rivers, and nearby beaches, perfect for outdoor enthusiasts.
  • Wine Country Experience: Located in Sonoma County, it's an ideal spot for wine tasting and vineyard tours.
  • Historic Downtown: The vibrant town square features shops, restaurants, and art galleries that highlight local culture.
  • Romantic Getaways: With its scenic views and cozy accommodations, Healdsburg is perfect for couples seeking a romantic escape.
  • Family-Friendly Activities: The welcoming atmosphere and various attractions make it a great destination for families.

Popular types of accommodation in Healdsburg

Healdsburg offers a delightful selection of vacation rentals, perfect for your getaway in California. Whether you're seeking a cozy private vacation home, a charming cottage, or a rustic cabin, you'll find the ideal spot to unwind. Explore our extensive Healdsburg vacation rental listings to discover the perfect house or home rental that suits your needs. Enjoy transparency, savings, and reassurance as you plan your next adventure in this picturesque wine country.

  • Houses: These spacious and comfortable homes are the top choice for visitors, ideal for families or groups seeking a home-like experience in Healdsburg.
  • Cottages: Charming and quaint, cottages offer a cozy atmosphere perfect for couples or small families looking for a peaceful getaway.
  • Cabins: For those who love nature, cabins provide a rustic escape surrounded by beautiful landscapes.
  • Apartments: Convenient and modern, apartments are great for travelers wanting a central location with easy access to local attractions.
  • Villas: Luxurious and spacious, villas offer upscale accommodations for those seeking an indulgent stay in Healdsburg.**

Top attractions in and around Healdsburg

Healdsburg is a charming destination perfect for outdoor enthusiasts and romantic getaways. Visitors can explore scenic spots like the piazza, rivers, and nearby beaches while enjoying a vibrant culture. Whether you're seeking adventure or a relaxing city experience, Healdsburg offers a delightful mix of attractions to make your vacation memorable.

  • Russian River: Located 4 miles from Healdsburg, this picturesque river is perfect for outdoor enthusiasts. Enjoy kayaking, tubing, or simply relaxing by the scenic banks surrounded by lush greenery.
  • Healdsburg Plaza: Situated in the heart of Healdsburg, this vibrant plaza is a cultural hub. Stroll through charming shops, dine at local restaurants, and soak in the lively atmosphere filled with art and community events.
  • Armstrong Redwoods State Park: Just 9 miles away, this stunning state park features towering redwoods and offers various hiking trails. Experience the beauty of nature and adventure among these ancient giants.

Things to do recommended for couples

Healdsburg offers a perfect romantic getaway for couples. Indulge in wine tasting at Dry Creek Vineyard, embark on an adventure with Rubicon Adventures, or enjoy a playful round at Pee Wee Golf and Arcade. Each experience is designed to create unforgettable memories together.

Things to do recommended for families

Families visiting Healdsburg will delight in Powell's Sweet Shoppe, a charming candy store located 5 miles away in Windsor. With its inviting atmosphere and a wide variety of sweet treats, it's the perfect spot for a fun and tasty family outing.

Things to do recommended for groups

Groups visiting Healdsburg can enjoy a round of golf at the Healdsburg Golf Club, catch a performance at the Raven Performing Arts Theater, and explore the unique offerings at Soda Rock Winery for a delightful blend of outdoor fun, culture, and local flavors.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Healdsburg

If you're traveling with a group, family, pets, or planning an extended stay, be sure to use the appropriate filters to match your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Healdsburg with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Healdsburg with young kids: Traveling with little ones can present some challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions for a more enjoyable experience.
  • Taking your pets with you to Healdsburg: For many, a family vacation wouldn’t feel complete without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Healdsburg: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Healdsburg

Healdsburg, California, is a charming destination perfect for outdoor enthusiasts and romantic getaways. Nestled in a breathtaking landscape, this town offers scenic views and historic charm. Explore the natural wonders nearby and enjoy the friendly atmosphere that makes for a relaxing family-friendly experience. With sunny weather and a welcoming community, Healdsburg invites you to embark on unforgettable excursions and discover the beauty of this delightful region.

  • Guerneville: Located 10 miles from Healdsburg, Guerneville is a charming city that offers a perfect blend of outdoor adventure and natural beauty. Nestled along the Russian River, this destination is ideal for those seeking scenic views and recreational activities. Visitors can enjoy kayaking on the river, relaxing at local beaches, or exploring the nearby Armstrong Redwoods State Natural Reserve, where towering trees create a breathtaking atmosphere. Guerneville also boasts several wellness centers and spas, perfect for unwinding after a day of exploration.
  • Windsor: Just 5 miles from Healdsburg, Windsor is a picturesque city known for its romantic ambiance and beautiful landscapes. This area is perfect for outdoor enthusiasts, with numerous parks and golf courses available. Windsor's charming piazza square offers a vibrant gathering place for events and live music, while the nearby Russian River provides opportunities for fishing and picnicking. Whether you’re enjoying a leisurely day on the golf course or strolling along the river, Windsor’s inviting atmosphere makes it a must-visit on your trip.
  • Geyserville: Situated 7 miles from Healdsburg, Geyserville is a hidden gem that combines outdoor beauty with romantic allure. This quaint city is known for its stunning views of the surrounding vineyards and nearby lake, making it perfect for couples and nature lovers alike. Visitors can explore recreational areas, indulge in spa treatments, or attend events at local conference venues. The serene landscape and charming local businesses create an inviting environment, making Geyserville a delightful addition to your travel itinerary.

Best time to go to Healdsburg

If you're planning a trip to Healdsburg, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and October, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January48.2°F (9.0°C)Light RainMostly SunnySlightly LowSlightly Low
February49.3°F (9.6°C)Light RainMostly SunnyAverageSlightly Low
March50.7°F (10.4°C)Light RainMostly SunnyAverageSlightly Low
April55.2°F (12.9°C)No Rain (Dry)Mostly SunnySlightly HighAverage
May60.3°F (15.7°C)No Rain (Dry)SunnyAverageAverage
June67.6°F (19.8°C)No Rain (Dry)SunnyAverageAverage
July70.7°F (21.5°C)No Rain (Dry)SunnySlightly HighAverage
August70.2°F (21.2°C)No Rain (Dry)SunnyAverageSlightly High
September68.2°F (20.1°C)No Rain (Dry)SunnyAverageSlightly High
October61.9°F (16.6°C)No Rain (Dry)SunnySlightly HighSlightly High
November52.9°F (11.6°C)Light RainMostly SunnySlightly LowAverage
December47.5°F (8.6°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, use our filters to search by price, location, and type of vacation rental. We’re here to help you find the perfect getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your reservation. Being the planner definitely has its perks. By enrolling in our travel rewards program, OneKey, you can immediately access member discounts and earn as well as redeem OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or manage your travel arrangements. You can easily access the properties you've saved and booked, now organized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Artsy Healdsburg will entice you

The area's wineries and art galleries are just a few of the reasons to vacation in Healdsburg. Well known for its restaurants, riverfront and shopping, this walkable city won't disappoint. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Healdsburg

Are you searching for attractions to visit in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Healdsburg a fun place to get away. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Jordan Vineyard & Winery (3.4 mi / 5.5 km)
  • Dry Creek Vineyard (4.2 mi / 6.8 km)
  • Francis Ford Coppola Winery (4.9 mi / 7.9 km)
  • Windsor Golf Club (6.7 mi / 10.8 km)
  • Korbel Winery (8.8 mi / 14.1 km)
  • Kendall-Jackson Wine Estate and Gardens (9.1 mi / 14.6 km)

Exploring the natural landscape of Healdsburg

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Healdsburg is a great place to spend some time outside. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Russian River (4.4 mi / 7 km)
  • Armstrong Redwoods State Park (9 mi / 14.5 km)
  • Kendall-Jackson Wine Estate and Gardens (9.1 mi / 14.6 km)
  • Safari West (10.1 mi / 16.3 km)
  • Johnson's Beach (10.3 mi / 16.6 km)
  • Lake Sonoma (10.9 mi / 17.6 km)

Traveling to and around Healdsburg

The nearest airport is in Santa Rosa, CA (STS-Sonoma County), located 7.7 mi (12.5 km) from the city center.

Frequently asked questions

What is the best area to stay in Healdsburg, California, United States of America when booking a vacation rental?
When booking a vacation rental in Healdsburg, California, one of the best areas to consider is the downtown district. This charming neighborhood is not only the heart of the town but also offers a delightful mix of boutique shops, art galleries, and exceptional dining options. Staying here puts you within walking distance of the beautiful Healdsburg Plaza, a lovely park surrounded by historic buildings and local eateries.

Another great option is the surrounding wine country, where you can find properties located among the vineyards. This area provides a serene and picturesque backdrop, great for enjoying the renowned wine tasting experiences that Healdsburg is famous for. You can easily explore local wineries and take in breathtaking views of the rolling hills.

Overall, Healdsburg boasts a variety of vacation rentals, from quaint cottages to luxurious homes, ensuring that visitors can find the great place to relax and enjoy all that this beautiful area has to offer.
How much does it cost to rent a vacation home in Healdsburg?
Prices for vacation rentals in Healdsburg vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Healdsburg to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Healdsburg vacation house rentals?
You can find great discounts on house rentals in Healdsburg on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Healdsburg?
In Healdsburg, vacation houses are the most popular type of accommodation, with about 118 available throughout the charming town. These properties often feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups. Many houses come with outdoor spaces, such as patios or gardens, great for enjoying the beautiful California weather and the surrounding vineyards. Additionally, there are around 18 cottages, which offer a cozy, quaint experience, typically with rustic decor and intimate settings. For those looking for a modern stay, approximately 10 apartments can be found, often located close to the town center, providing easy access to local shops and restaurants. Villas and condos are also available, though in smaller numbers, offering luxury amenities and additional privacy.
Are there any family house rentals in Healdsburg?
In Healdsburg, California, there are plenty of family-friendly house rentals available—around 110 options throughout the area. The charming downtown is a great place to start, where visitors can enjoy the local boutiques, restaurants, and tasting rooms. Many homes in this locale feature spacious living areas, fully equipped kitchens, and outdoor patios or gardens great for family gatherings and barbecues.

Additionally, some properties may offer amenities like game rooms or private pools, providing entertainment for children and relaxation for adults. Healdsburg is also situated near beautiful parks and vineyards, making it an ideal location for families looking to explore nature or enjoy wine tasting while the kids have fun outdoors.
Can I rent a vacation home with a pool or hot tub in Healdsburg?
In Healdsburg, there are plenty of vacation homes available for rent that feature both pools and hot tubs, with around 64 options to choose from. This picturesque town in Sonoma County is known for its beautiful vineyards and charming downtown area. Travelers can find properties in various neighborhoods, offering a mix of tranquil rural settings and proximity to the vibrant town center.

Many of these rentals come equipped with private pools, inviting hot tubs, and spacious outdoor areas superb for relaxation and entertaining. Inside, guests can expect fully equipped kitchens, comfortable living spaces, and often amenities like Wi-Fi and air conditioning. Some homes may even offer stunning views of the surrounding vineyards or access to outdoor activities such as hiking and wine tasting. Find your rental in Healdsburg with a pool or a hot tub.
Can I find long-stay vacation rentals in Healdsburg?
A long-stay vacation rental in Healdsburg is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Healdsburg?
In Healdsburg, travelers can find a variety of pet-friendly house rentals, with around 71 options available to choose from. The area is known for its picturesque vineyards and charming small-town atmosphere, making it a delightful place for both you and your furry friends. Many vacation rentals in Healdsburg come equipped with amenities such as spacious outdoor areas, fully stocked kitchens, and cozy living spaces that make for a comfortable stay.

The downtown area is particularly inviting, featuring pet-friendly parks and restaurants where your pets are welcome. Visitors can enjoy leisurely strolls along the Russian River or explore the scenic walking trails nearby.
Are there any remote work vacation rentals in Healdsburg?
In Healdsburg, there is a wide selection of remote work vacation rentals available, with about 146 options to choose from. This charming town in Sonoma County is not only known for its picturesque vineyards and wine country but also offers a conducive environment for remote work. Many properties provide essential amenities such as dedicated workspaces with desks and comfortable chairs, high-speed internet, and Wi-Fi, ensuring a productive stay.

Travelers can expect a range of accommodations, from cozy cottages located among the vineyards to spacious homes with modern furnishings. The properties often include additional conveniences like fully equipped kitchens, outdoor spaces for relaxation, and sometimes even stunning views of the surrounding countryside.

Healdsburg's vibrant downtown area is just a short distance away, featuring excellent dining options, boutique shops, and art galleries, making it easy to unwind after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Healdsburg vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Healdsburg with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Healdsburg?
In Healdsburg, popular rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals using local ingredients. Most rentals also feature outdoor spaces like decks or patios, great for enjoying the scenic views of wine country. Onsite parking is commonly available, making it convenient for those exploring the region by car. Additionally, many properties provide coffee and tea makers, ensuring that guests can start their day with a warm beverage while taking in the beautiful surroundings.
When is the best time to visit Healdsburg for a vacation rental?
The best time to visit Healdsburg for a vacation rental is during the peak season from August to October, with October being particularly popular. This enchanting month marks the height of the grape harvest, making it a vibrant time for wine enthusiasts eager to explore the renowned wineries of Sonoma County. Guests can indulge in wine tastings and enjoy the picturesque vineyards adorned in autumn hues, creating a stunning backdrop for outdoor activities.

During this period, the weather is typically warm and pleasant, with temperatures ranging from the mid-50s to mid-70s Fahrenheit, ideal for leisurely strolls through the charming downtown area or enjoying al fresco dining at local restaurants. The atmosphere is lively, yet the fall season brings a sense of tranquility as the summer crowd begins to wane.

For those looking for more budget-friendly options, December can offer a quieter experience. It's cooler, with temperatures dipping into the 30s and 40s Fahrenheit, visitors can appreciate the festive ambiance of the holiday season and take advantage of lower rental rates. This time of year provides a unique opportunity to enjoy Healdsburg's cozy charm, with fewer tourists and a chance to explore local shops and events at a more leisurely pace.
How early should I book a Healdsburg vacation rental?
Book your Healdsburg vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Healdsburg, California, United States of America?
In Healdsburg, visitors can experience firsthand a charming blend of wine country and small-town atmosphere. The downtown area is a hub for boutique shops, art galleries, and farm-to-table restaurants, making it a delightful spot to explore local flavors and craftsmanship. The Healdsburg Plaza is a central landmark, often bustling with events and farmers' markets.

Wine enthusiasts will appreciate the proximity to world-renowned wineries in the surrounding Sonoma County, particularly along the Dry Creek Valley and Russian River Valley, where tastings and vineyard tours offer a glimpse into the region's rich viticulture.

For outdoor activities, the nearby Russian River provides opportunities for kayaking, canoeing, and picnicking along scenic banks. Additionally, the area features picturesque hiking trails, such as those found in the nearby Armstrong Redwoods State Natural Reserve, where visitors can marvel at towering ancient trees amidst tranquil surroundings.
Can I change or cancel my Healdsburg home rental booking on Vrbo?
To find Healdsburg vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Healdsburg vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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