Healdsburg vacation rentals

We found 576 vacation rentals — enter your dates for availability

Discover a selection of 138 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:Mar 13 - Mar 20

Image gallery for Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Pool
10 out of 10, Exceptional, (66 reviews)
Exceptional
(66 reviews)

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Healdsburg, CA

15% off
Price is CA $2,241
CA $19,245 total
includes taxes & fees
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

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Find out more about Healdsburg

Why visit Healdsburg

  • Charming downtown: Healdsburg's vibrant city centre offers unique shops, delightful eateries, and a welcoming atmosphere for visitors.
  • Outdoor adventures: Enjoy a variety of activities amidst stunning landscapes, including rolling hills and majestic coast redwoods.
  • Cultural attractions: Explore the Healdsburg Museum and Decanter Healdsburg for a taste of local history and art.
  • Relaxing accommodations: Choose from cozy vacation rentals, including charming cottages and spacious homes for a comfortable stay.
  • Family-friendly vibe: With friendly locals and plenty of sunshine, Healdsburg is perfect for family getaways and romantic escapes.

Popular types of accommodation in Healdsburg

Planning a getaway to Healdsburg? You're in for a treat. This charming destination offers a variety of vacation rentals, with houses, cottages, and cabins being the most sought-after options. Discover your perfect Healdsburg vacation rental and enjoy a memorable stay filled with comfort and convenience. Whether you're looking for a cozy cabin or a spacious vacation home, you'll find the ideal spot to unwind and explore the beauty of this picturesque locale.

  • Houses: The top choice for visitors to Healdsburg, offering spacious and comfortable accommodations ideal for families, friends, or couples.
  • Cottages: A delightful option for a quaint and cozy experience, perfect for those seeking a serene getaway.
  • Cabins: These rustic retreats provide a charming escape, set amidst nature for outdoor enthusiasts.
  • Apartments: A convenient choice for travellers wanting easy access to local amenities and attractions.
  • Villas: Luxurious and spacious, villas offer an upscale experience for those looking to indulge during their stay.**

Top attractions in and around Healdsburg

Healdsburg, California, is ideal for outdoor enthusiasts and romantic getaways, featuring beautiful piazzas, rivers, and nearby beaches. Visitors can explore cultural attractions like the Healdsburg Museum, the vibrant city centre, and Decanter Healdsburg. With a wealth of outdoor activities and scenic experiences, Healdsburg promises an unforgettable vacation that blends natural beauty with local charm.

  • Russian River: A picturesque river located 6.4km from Healdsburg, offering stunning scenery and a vibrant outdoor atmosphere perfect for kayaking, tubing, or simply enjoying a peaceful picnic by the water.
  • Healdsburg Plaza: Situated in the heart of Healdsburg, this charming square is a cultural hub filled with shops, restaurants, and art galleries, providing a lively city vibe where you can relax and soak in the local culture.
  • Armstrong Redwoods State Park: Located 14.5km from Healdsburg, this majestic park features towering redwoods and scenic trails, ideal for adventure enthusiasts looking to hike, bike, or explore nature's beauty.

Things to do recommended for couples

Healdsburg offers a delightful escape for couples. Enjoy a romantic wine tasting at Dry Creek Vineyard or Francis Ford Coppola Winery. For a bit of fun, venture 16.1km to Pee Wee Golf and Arcade for a playful round of mini-golf together, creating lasting memories.

Things to do recommended for families

Families visiting Healdsburg can enjoy a delightful outing at Powell's Sweet Shoppe in Windsor, located 8.0km away. This charming sweet shop offers a family-friendly atmosphere, perfect for indulging in delicious treats and creating sweet memories together.

Things to do recommended for groups

Groups visiting Healdsburg can enjoy a round of golf at the Healdsburg Golf Club, experience cultural performances at the Raven Performing Arts Theater, and indulge in wine tasting at Soda Rock Winery, all while soaking in the charming California atmosphere.

*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

When planning your trip—whether with a group, family, pets, or for an extended stay—be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Healdsburg with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Healdsburg with young kids: Traveling with young children can be quite a task. It's important to prioritize their comfort and safety, as well as seek out child-friendly amenities like a private swimming pool. Additionally, considering how close you are to family-oriented attractions can enhance your experience.
  • Taking your pets with you to Healdsburg: For many families, a getaway wouldn’t feel complete without their furry companion. If you can relate, explore Vrbo listings that welcome pets. Many of these 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 that offer 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.

Where to stay near Healdsburg

Healdsburg, California, offers an enchanting blend of outdoor adventures and romantic scenery. Explore the charming downtown area, unwind in the tranquil Solace in Healdsburg, and marvel at the breathtaking rolling hills and majestic coast redwoods. This family-friendly destination is perfect for those seeking a relaxing atmosphere, friendly locals, and plenty of sunshine. Nearby neighborhoods also provide a welcoming vibe, making your vacation a memorable experience amidst nature's beauty.

  • Guerneville: Nestled approximately 16.1km from Healdsburg, Guerneville is a vibrant destination known for its stunning natural scenery and outdoor adventure opportunities. The Russian River meanders through this charming town, providing a perfect backdrop for kayaking, swimming, and relaxing on the beach. Guerneville is also home to the picturesque Armstrong Redwoods State Natural Reserve, where visitors can wander among towering ancient trees. The local spa and body treatment venues offer rejuvenation after a day of exploration, making it a well-rounded getaway for those seeking both adventure and relaxation.
  • Windsor: Located a mere 8.0km from Healdsburg, Windsor is a delightful city that combines scenic beauty with a romantic atmosphere. The town features lush parks and well-maintained golf courses, making it an ideal spot for outdoor enthusiasts. Stroll through the lovely Piazza Square, where you can enjoy boutique shopping and casual dining. The nearby Russian River and its serene beaches create a perfect setting for a leisurely day outdoors or a romantic picnic. Windsor is a charming blend of nature and community, making it a great choice for a relaxing getaway.
  • Geyserville: Situated about 11.3km from Healdsburg, Geyserville is an enchanting small town that offers a mix of outdoor experiences and romantic charm. Known for its beautiful landscapes, Geyserville is a gateway to various recreational areas, including nearby lakes and rivers perfect for fishing and boating. Visitors can indulge in local body treatments and spa services, enhancing the overall experience. The town also hosts event conference venues that attract visitors year-round. With its captivating views and relaxing atmosphere, Geyserville is a hidden gem waiting to be explored.

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

Are you planning your next getaway and hoping to save some money? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even more savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to narrow down options by price, location, and type of vacation rental. We're here to help you find the perfect spot for your travels.

Vrbo Trips: Planning made easy

Vrbo's user-friendly Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, or easily view and organize your travel arrangements. You can conveniently find the properties you've saved or booked in the Potential, Upcoming, or Current Trips sections. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/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)
  • SingleThread Farm at Dry Creek (3.5 mi / 5.7 km)
  • Mazzocco Winery (3.6 mi / 5.7 km)
  • Dry Creek Vineyard (4.2 mi / 6.8 km)
  • Francis Ford Coppola Winery (4.9 mi / 7.9 km)
  • Korbel Winery (8.8 mi / 14.1 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 when booking a vacation rental?
When considering a vacation rental in Healdsburg, California, a popular area to stay is the charming downtown district. This vibrant neighbourhood is renowned for its delightful array of shops, restaurants, and tasting rooms, making it a great base for exploring the local wine culture. With a variety of properties available, from quaint cottages to more spacious homes, visitors can easily find something that suits their needs.

Staying in downtown Healdsburg places you just a short stroll away from the Healdsburg Plaza, a lovely park surrounded by historic buildings and lively outdoor seating areas. This area often hosts events and markets, providing a wonderful opportunity to engage with the local community. Additionally, the proximity to renowned wineries, such as those along the Russian River and in the surrounding Sonoma County, makes it convenient for wine enthusiasts to indulge in tastings and vineyard tours.

Another fantastic option is the Dry Creek Valley region, which is slightly more rural but equally enchanting. This area is famous for its stunning landscapes and offers a serene retreat for those looking to unwind. The properties here often boast beautiful views and a more spacious setting, great for families or larger groups. Not far from your doorstep, the Dry Creek General Store is a local favourite for gourmet snacks and picnic supplies, while the nearby wineries provide an idyllic backdrop for leisurely afternoons.
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 travelling 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.
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.
Where are the best areas for renting a beach house in Healdsburg?
For renting a beach house in Healdsburg, California, while the town itself is not directly on the coast, you can find attractive options along the Russian River, which offers a serene riverside experience. The area near Riverfront Regional Park is particularly appealing, where you can discover properties that provide easy access to the riverbank and nearby swimming spots. Many of these rentals feature amenities like spacious outdoor decks, BBQ facilities, and fully equipped kitchens, ideal for families or groups wanting to enjoy a relaxed getaway.

Additionally, heading towards the nearby coastal towns such as Jenner or Bodega Bay, you'll find beach houses with stunning ocean views and easy access to sandy beaches. These properties often come with amenities such as fire pits, outdoor dining areas, and some may even include hot tubs, great for unwinding after a day of exploration.
What is the most popular type of vacation rental accomodation in Healdsburg?
In Healdsburg, vacation houses are the predominant type of rental, with around 120 available in this charming wine country town. These properties are often situated near the picturesque downtown area, where guests can explore local wineries, gourmet restaurants, and the vibrant Healdsburg Plaza. Most vacation houses feature spacious layouts, fully equipped kitchens, outdoor patios or gardens, and amenities like barbecues, making them ideal for families or groups looking to enjoy a home-away-from-home experience.
Are there any family house rentals in Healdsburg?
In Healdsburg, California, there are numerous family-friendly house rentals available—specifically, around 117 options. This charming town is located in the heart of Sonoma County, making it a fantastic choice for families looking to explore the region. Many homes in the area feature spacious living rooms, fully equipped kitchens for preparing meals, and outdoor patios or gardens great for children to play in.
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 pools and hot tubs, with approximately 68 options to choose from. This charming town in Sonoma County is renowned for its picturesque vineyards and culinary delights, making it a popular destination for travellers seeking relaxation and indulgence.

Many of the properties in Healdsburg come with private pools and hot tubs, set in beautifully landscaped gardens, providing a superb setting for unwinding after a day of wine tasting or exploring the local area. Travellers can expect amenities such as fully equipped kitchens, outdoor dining areas, and spacious living rooms, ideal for family gatherings or socialising with friends. 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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Healdsburg?
In Healdsburg, there are numerous pet-friendly house rentals available, with about 68 options to choose from. This charming town, renowned for its picturesque vineyards and vibrant culinary scene, offers a variety of accommodations that cater to pet owners. Many of these rentals feature amenities such as spacious gardens, outdoor seating areas, and fully equipped kitchens, allowing for a comfortable stay while enjoying the beautiful surroundings.
Are there any remote work vacation rentals in Healdsburg?
In Healdsburg, California, there is a substantial selection of remote work vacation rentals available, with around 152 options for travellers seeking a productive getaway. This charming town in Sonoma County is renowned for its picturesque vineyards and vibrant culinary scene, making it an ideal backdrop for both work and leisure. Many of the properties are equipped with dedicated office spaces, desks, and high-speed Wi-Fi, ensuring a comfortable work environment. 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 travellers 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, allowing guests to prepare their own meals with ease. Many properties feature patios where visitors can relax outdoors and enjoy the pleasant Californian weather. Additionally, travellers can expect essential cookware, dishware, and utensils, along with modern appliances like microwaves and ovens, making it convenient for those who prefer a home-cooked experience during their stay.
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 ushers in the harvest season, when vineyards are alive with activity, and visitors can indulge in wine tastings and tours amidst the picturesque landscapes of Sonoma County.

During this period, the weather is typically delightful, with daytime temperatures in the mid to high teens Celsius. This pleasant climate makes it ideal for outdoor activities such as cycling through the scenic wine country, exploring charming downtown Healdsburg, or enjoying leisurely picnics in the abundant parks.

For those looking for a more budget-friendly option, December offers a quieter experience. While it's the low season, visitors can still enjoy Healdsburg's festive charm with vacation events and smaller crowds, making it a wonderful time to relax and explore the local shops and eateries 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?
In Healdsburg, visitors can enjoy a variety of attractions that showcase the region's charm and natural beauty. The town square is a central hub, surrounded by quaint shops, cafes, and wine tasting rooms, making it an ideal spot for vacation rentals. Nearby, the Russian River offers opportunities for outdoor activities such as kayaking and river tubing, providing a relaxing way to experience the area's natural landscape.
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 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 travellers 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 cosy cabin or a beach house, 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.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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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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