Healdsburg holiday rentals

We found 586 holiday rentals — enter your dates for availability
Discover a selection of 143 homes, 11 apartments and other holiday rentals in Healdsburg that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for spending time at your holiday home, including parking and a TV. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Healdsburg

Showing deals for:9 Oct - 16 Oct

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Why visit Healdsburg

  • Charming downtown: Enjoy boutique shops, delightful eateries, and captivating art galleries in a vibrant city centre.
  • Scenic river views: Wander along the picturesque piazza and relax by the calming river, perfect for leisurely strolls.
  • Cultural insights: Visit the local museum to uncover the rich history of this quaint Californian town.
  • Outdoor delights: Cycle through nearby vineyards and explore the natural beauty surrounding the city.
  • Inviting ambience: Experience a friendly atmosphere with a blend of relaxation and adventure in a sun-drenched setting.

Popular types of accommodation in Healdsburg

Welcome to Healdsburg, California’s charming retreat, where scenic vineyards and local delights await. Here, you can indulge in a range of private holiday homes, cosy cottages, and secluded cabins. Discover thoughtful, luxurious accommodations—from hidden Healdsburg hideaways to modern hotels with premium amenities and exclusive complimentary stays—for an unforgettable experience in this idyllic Californian town.

  • Private Holiday Homes: These fully equipped residences offer a home-away-from-home experience, providing comfort and privacy for families or groups.
  • Cottages: Quaint and charming, cottages provide a delightful retreat, often nestled in picturesque surroundings ideal for relaxation.
  • Cabins: Rustic and cosy, cabins are perfect for those seeking a nature-inspired getaway, often featuring wooden interiors and scenic views.
  • Apartments: Conveniently located, apartments offer a blend of comfort and accessibility, making them suitable for couples or solo travellers.
  • Villas: Luxurious and spacious, villas provide upscale amenities and often stunning vistas, perfect for a lavish holiday experience.**

Top attractions in and around Healdsburg

Healdsburg, California, offers a delightful blend of outdoor activities and cultural experiences for visitors. Explore the charming piazza and enjoy scenic river views, perfect for leisurely walks. The local museum provides insight into the area's rich history, making it a must-visit for culture enthusiasts. With its picturesque surroundings, Healdsburg is an ideal destination for those seeking both relaxation and adventure in a vibrant city atmosphere.

  • Healdsburg Plaza: A charming public square that serves as the heart of Healdsburg, featuring beautiful gardens, vibrant local arts, and a variety of shops and eateries that reflect the town's culture.
  • Russian River: A picturesque river perfect for outdoor activities such as kayaking, swimming, and picnicking amidst stunning natural scenery, just a short drive from the town centre.
  • Armstrong Redwoods State Park: A serene park known for its towering ancient redwoods, offering hiking trails that invite adventure and exploration in a breathtaking natural setting.

Things to do recommended for couples

Healdsburg offers a charming escape for couples. Enjoy a leisurely wine tasting at a local vineyard, stroll hand-in-hand along the picturesque Plaza, or indulge in a romantic dinner at a cosy restaurant. Don't miss the breathtaking sunset views over the vineyards for a truly memorable experience.

Things to do recommended for families

Families will delight in exploring the scenic Healdsburg Plaza, where they can enjoy local shops and eateries, or take a leisurely stroll along the Russian River. The nearby Armstrong Redwoods State Natural Reserve offers enchanting hikes suitable for all ages amidst towering trees.

Things to do recommended for groups

Experience the thrill of motor racing at Calistoga Speedway, only 24km from Healdsburg, or soar through the treetops at Sonoma Zipline Adventures, located 21km away. Both activities promise adventure and excitement for your group amidst the stunning Californian landscape.

*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 you're travelling with a group, family, pets, or seeking longer stays, it's essential to filter your options according to your key priorities. Here are some helpful Stayz booking tips for you.

  • Traveling to Healdsburg with a group: Take into account the number of bedrooms required, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can refine your search for all these options and more on Stayz.
  • Traveling to Healdsburg with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it’s wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Healdsburg: For many, a family holiday isn’t truly complete without their furry companion by their side. If this resonates with you, consider exploring Stayz properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Healdsburg: If you're in search of holiday rentals that offer discounts for month-long stays, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include additional preferences in your search, such as a parking space, a well-equipped kitchen, or even a private pool.

Where to stay near Healdsburg

Healdsburg, California, is a charming city perfect for a family getaway or an outdoor adventure. Visitors can explore the vibrant downtown filled with boutique shops, delightful eateries, and stunning art galleries. The area is known for its sunny weather, making it ideal for biking around picturesque vineyards and enjoying scenic excursions. With its friendly atmosphere and relaxing environment, Healdsburg promises a wonderful holiday experience that captures the essence of Californian charm.

  • Guerneville: Nestled approximately 16km from Healdsburg, Guerneville is a charming riverside town known for its stunning natural beauty and vibrant outdoor activities. Surrounded by towering redwoods, the area offers ample opportunities for adventure, including hiking, kayaking, and exploring the nearby state parks. The scenic Russian River adds to the allure, providing a perfect backdrop for relaxation and recreation. Visitors can indulge in rejuvenating body treatments and spa experiences, making it an ideal destination for those seeking both adventure and serenity.
  • Windsor: Located a mere 8km from Healdsburg, Windsor is a delightful city celebrated for its picturesque scenery and romantic atmosphere. This charming locale boasts beautiful parks and a vibrant piazza square, making it perfect for leisurely strolls. Golf enthusiasts will appreciate the well-maintained golf courses, while couples can enjoy a peaceful day by the river or partake in various outdoor activities. The town’s inviting ambiance and lush landscapes create a lovely setting for relaxation and exploration.
  • Alexander Valley: Just 8km from Healdsburg, Alexander Valley is renowned for its world-class wineries and breathtaking vineyards. The region offers an enchanting mix of outdoor and entertainment-themed experiences, allowing visitors to immerse themselves in the local wine culture. Enjoy spa treatments and recreational activities amidst the stunning landscapes, where the rolling hills and serene rivers create a picturesque backdrop. The area’s charm and romantic setting make it a must-visit for wine lovers and those seeking a tranquil escape.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 Stayz is a breeze

Are you hoping to save on your next adventure? It’s worth being flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to considerable savings. To discover the ideal Stayz property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Trip Board by Stayz offers a dedicated space to craft new journeys, resume where you previously paused, or simply review and arrange your plans. Properties that you have saved or booked now appear under Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.stayz.com.au/trips

**Based on Vrbo properties bookings.

Arty Healdsburg will entice you

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

Activities and attractions in and around Healdsburg

Are you hoping to find attractions to visit during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Healdsburg a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Trentadue Winery (4.9 mi / 7.9 km)
  • Windsor Golf Club (6.7 mi / 10.8 km)

Exploring the natural landscape of Healdsburg

Whether you're looking for adventure or just want to take in the scenery, Healdsburg is a great place to spend some time outside. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Travelling 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 centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Healdsburg?
The most popular types of holiday homes in Healdsburg are houses. Looking for something different? Stayz has numerous options to match our guests' diverse needs, so you'll see holiday properties in all shapes and sizes, and for all budgets. The ideal home away from home is waiting for you — lock in yours today.
How much does it cost to rent a holiday home in Healdsburg?
The average price for a holiday home in Healdsburg is determined by a number of factors, including length of stay, season and property type. Whether you're in search of a sprawling villa with a pool or a comfy cabin that's perfect for two, just add your travel dates to find stays that offer great value.
How much does it cost to rent a beach house in Healdsburg?
Prices for beach houses in Healdsburg can vary depending on the style and size of the property and time of year you're travelling. All you have to do is enter your travel dates into Stayz and how many guests to view holiday home options and prices. From there you can use our filters to narrow down your search by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday homes in Healdsburg?
Yes. There are. Choose from 15 holiday homes that welcome pets in Healdsburg on Stayz. Our furry friends deserve a getaway too, so simply use our search function for pet-friendly holiday homes to find a property where your puppy dog can get in on the fun.
Can I rent a house with a pool in Healdsburg?
Pack your swimming gear and pool noodle, because there are three houses with a private pool in Healdsburg. Make a booking at one of these superb holiday homes and you'll enjoy pool days every day. Simply enter your dates into Stayz, then check the "pool" filter to find the perfect place to make a splash!
What are popular home amenities in Healdsburg?
Some of the most popular home amenities people prefer in Healdsburg include mountain views, a chef and nearby museums. Whether you're holidaying with buddies, family or even pets, Stayz holiday properties provide the best amenities for fun and relaxation with the people you love.
Are there large group holiday homes in Healdsburg?
Take your pick of five Stayz properties in Healdsburg that can host five or more guests. You'll get all the privacy and room you need to kick back with your loved ones — and nobody else.
Are there holiday homes in Healdsburg that welcome kids?
Healdsburg has 15 family-friendly holiday homes to pick from. And tracking down a stay that welcomes youngsters is super easy with Stayz's "Properties good for families" filter. In addition to having the entire place to yourselves, you'll get perks and amenities such as dining rooms, yards and private pools.
What are the top attractions for families in Healdsburg?
Keeping the kids occupied during your holiday in Healdsburg is child's play with these top family-friendly attractions:

  • Pacific Coast Air Museum
  • Healdsburg Museum
  • Armstrong Redwoods State Park

Are there one-bedroom holiday homes in Healdsburg?
Healdsburg has five one-bedroom homes on offer. Often located in sought-after areas thanks to their smaller size, a one-bedroom holiday property is great if you're getting away with a pal or your partner. And with home comforts like full kitchens and more privacy than a standard hotel, you'll be able to relax while sightseeing around this incredible destination.
Can I find two-bedroom holiday homes in Healdsburg?
Gather your loved ones and relax in total privacy and comfort in one of the five two-bedroom holiday homes Healdsburg has to offer.
Are there holiday homes with WiFi in Healdsburg?
Take your pick of seven holiday homes with WiFi in Healdsburg. If you'd like to disconnect from the world during your escape, but still want to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Healdsburg?
Healdsburg has 15 holiday homes where you can relax and recharge in air-conditioned comfort. To find a property on Stayz that comes with this amenity, enter your travel dates and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Healdsburg?
The age limit can differ across properties on Stayz, so double-check the rules of the holiday home in Healdsburg you're interested in. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Healdsburg for?
How long you can book a holiday home in Healdsburg differs according to the property. Just enter your chosen travel dates to look at a list of options offering extended stays. With plenty of amenities such as air conditioning and kitchens, as well as some offering weekly or monthly discounted prices, you're sure to find someplace just right to call your home away from home in Healdsburg.