Healdsburg vacation rentals

We found 598 vacation rentals — enter your dates for availability

Discover a selection of 143 homes, 12 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:Nov 28 - Dec 5

Image gallery for Spectacular View Estate 5min Away

Pool
10 out of 10 rating
Exceptional
(23 reviews)

Spectacular View Estate 5min Away

Healdsburg, CA

7% off
Price is $3,564
$24,945 for 7 nights
All fees included
Spectacular View Estate 5min Away

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Find out more about Healdsburg

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:

  • Wilson Winery (2.6 mi / 4.2 km)
  • Jordan Vineyard & Winery (3.4 mi / 5.5 km)
  • SingleThread Farm at Dry Creek (3.5 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 downtown district. This vibrant neighborhood is the heart of Healdsburg, offering a charming mix of boutique shops, gourmet restaurants, and local wineries. Staying in downtown means you'll be just steps away from the Healdsburg Plaza, a lovely park surrounded by historic buildings and a superb spot to relax or enjoy local events. You'll also find the Healdsburg Museum nearby, which offers insights into the area's rich history and culture.

Another great option is the Westside Road area, known for its picturesque vineyards and stunning views of the Russian River. This area is superb for those who want a more tranquil experience, as it's surrounded by nature and offers easy access to some of the region's most renowned wineries, such as those in the Dry Creek Valley.
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.
Where are the best areas for renting a beach house in Healdsburg?
For renting a beach house in Healdsburg, California, travelers should consider properties along the Russian River, which flows through this picturesque wine country town. The area near the river offers various vacation rentals, including charming cabins and modern homes that often come equipped with amenities such as private decks, outdoor barbeques, and river access for swimming or kayaking. Many properties in this region feature spacious living areas, full kitchens, and beautiful views of the surrounding vineyards and redwoods, making them great for families or groups looking to relax and unwind.

Additionally, the nearby Lake Sonoma area provides further options for those seeking a more secluded experience. Rentals here can range from cozy lakeside cottages to larger homes with expansive outdoor spaces, often including amenities like fire pits, hot tubs, and picnic areas. This location offers not only the chance to enjoy water activities but also hiking trails and picnic spots that allow travelers to immerse themselves in the natural beauty of the region.

Healdsburg itself is known for its vibrant culinary scene, with many local restaurants and vineyards nearby, adding to the overall experience. Find your rental near the beach in Healdsburg.
What is the most popular type of vacation rental accomodation in Healdsburg?
In Healdsburg, vacation houses are the most popular type of rental, with about 119 available throughout the area. These homes are often situated in charming neighborhoods close to wineries and the picturesque downtown plaza, providing guests with easy access to local restaurants and shops. Most vacation houses come equipped with amenities such as fully stocked kitchens, spacious living areas, and private outdoor patios or gardens, great for enjoying the beautiful California weather.

Additionally, there are around 21 cottages available, offering a more rustic and cozy experience. These typically feature charming interiors, often with wood-burning fireplaces and outdoor spaces for relaxation. For those seeking a more compact option, about 10 apartments can be found, usually located within walking distance of the vibrant Healdsburg square.

There are also several villas and condos, which provide a mix of luxury and convenience, often featuring pools, modern kitchens, and scenic views of the surrounding vineyards.
Are there any family house rentals in Healdsburg?
In Healdsburg, California, family-friendly vacation homes are plentiful, with around 112 options available. This charming town is situated in the heart of wine country, offering a delightful blend of activities for all ages. Visitors can explore various neighborhoods, each with its own unique character and proximity to local attractions.

Properties in the Healdsburg area often feature spacious living rooms, fully equipped kitchens for family meals, and outdoor areas for relaxation or play. Many homes come with amenities like private pools, game rooms, and BBQ grills, great for family gatherings after a day of exploration.

Located near the picturesque Healdsburg Plaza, families can easily access delightful shops, parks, and restaurants. The town is also close to beautiful vineyards and outdoor activities such as hiking along the Russian River, ensuring a memorable experience for everyone. See all family-friendly rentals in Healdsburg.
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 around 68 options to choose from. This picturesque town in Sonoma County is renowned for its beautiful vineyards and charming downtown area. Travelers can find rentals in various neighborhoods, including the scenic Dry Creek Valley and the wine country estates surrounding the town.

Many of these homes come equipped with private pools and hot tubs, superb for relaxation after a day of wine tasting or exploring the local shops and restaurants. Additional amenities often include spacious outdoor areas with patios, fully equipped kitchens for preparing meals, and comfortable living spaces that cater to families or groups. 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 a total of 69 options available. This charming wine country town offers a mix of cozy cottages and spacious homes, often equipped with amenities such as private backyards, fully equipped kitchens, and outdoor patios, providing a comfortable stay for both guests and their furry companions.

The surrounding area is known for its picturesque vineyards and beautiful landscapes, making it an ideal location for pet owners who enjoy outdoor activities. Nearby parks, such as Healdsburg Memorial Beach and the scenic trails along the Russian River, provide great opportunities for walks and relaxation with pets. Additionally, the town features several pet-friendly wineries and outdoor dining options, allowing pets to join their owners while they savor the local wines and cuisine. See all pet-friendly rentals in Healdsburg.
Are there any remote work vacation rentals in Healdsburg?
In Healdsburg, there are numerous remote work-friendly vacation rentals available, with around 151 options to choose from. This picturesque town in Sonoma County is known for its beautiful vineyards, charming downtown area, and vibrant culinary scene, making it an ideal spot for both work and leisure. Many properties come equipped with essential remote work amenities, including high-speed Wi-Fi, dedicated office spaces, ergonomic desk chairs, and laptop workstations.

Travelers can expect to find accommodations that feature spacious living areas, full kitchens, and outdoor patios, allowing for a comfortable work environment alongside opportunities to unwind. Proximity to local wineries, art galleries, and the scenic Russian River adds to the appeal of working remotely in this area. 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 vacation rental amenities include WiFi, kitchens, and patios, making it easy for travelers to stay connected, prepare meals, and enjoy the lovely California weather. Many rentals also feature blenders and coffee/tea makers, allowing guests to whip up smoothies or enjoy a morning brew while taking in the views of the surrounding vineyards and charming downtown area.
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 highlight the beauty of Sonoma County. The town's charming Plaza is surrounded by boutique shops, art galleries, and renowned restaurants, making it a bustling hub for both locals and tourists. Nearby, the Russian River offers opportunities for kayaking and swimming, while picturesque wineries dot the landscape, particularly along the Dry Creek Valley and Alexander Valley, where wine tasting experiences abound.

For those interested in outdoor activities, the nearby Healdsburg Ridge Open Space Preserve features hiking trails with scenic views of the surrounding vineyards and hills. Additionally, the area is known for its vibrant culinary scene, with many establishments sourcing ingredients from local farms and providing farm-to-table dining experiences.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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