Healdsburg vacation rentals

We found 589 vacation rentals — enter your dates for availability

Discover a selection of 142 homes, 13 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

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Find out more about Healdsburg

Find out more about Healdsburg

Why visit Healdsburg

  1. Scenic Vineyards: Explore the picturesque vineyards and enjoy wine tasting in the heart of wine country.
  2. Charming Downtown: Stroll through the historic downtown area, featuring unique shops, galleries, and the lively piazza.
  3. Outdoor Activities: Engage in various outdoor pursuits, including hiking, biking, and kayaking along the scenic river.
  4. Romantic Getaways: Experience a serene atmosphere perfect for couples seeking a romantic retreat.
  5. Cozy Accommodations: Choose from delightful vacation rentals like cottages and rustic cabins for a comfortable stay.

Popular types of accommodation in Healdsburg

Discover the charm of Healdsburg with our selection of vacation rentals, including houses, cozy cottages, and rustic cabins. Whether you're planning a family getaway or a romantic retreat, we have the perfect rental homes to suit your needs. With a variety of house rentals in Healdsburg, you can enjoy a comfortable stay surrounded by the stunning beauty of wine country. Explore your options and find the ideal accommodation for your next adventure!

  • Houses: The top choice for visitors to Healdsburg, these homes offer spacious accommodations perfect for families or groups seeking comfort and privacy.
  • Cottages: A close second, these charming retreats provide a cozy atmosphere ideal for couples or solo travelers looking for a quaint getaway.
  • Cabins: Popular for those wanting a rustic experience, cabins offer a serene escape immersed in nature.
  • Apartments: These versatile spaces are great for travelers seeking convenience and a home-like feel during their stay.
  • Villas: For a touch of luxury, villas provide upscale amenities and stunning views, perfect for a memorable vacation.**

Top attractions in and around Healdsburg

Healdsburg is a picturesque destination perfect for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can explore popular attractions like the charming piazza, scenic river, and serene lake. The area offers a rich blend of outdoor activities, cultural experiences, and vibrant city life, making it an ideal spot for travelers looking to immerse themselves in nature and local culture.

  1. Russian River: Located 4 miles from Healdsburg, the Russian River offers stunning scenery and a relaxed outdoor atmosphere perfect for kayaking, tubing, or simply enjoying a picnic by the water.
  2. Healdsburg Plaza: Situated in the heart of Healdsburg, this vibrant plaza is a cultural hub filled with shops, restaurants, and art, making it a great spot to soak up the local city vibes.
  3. Armstrong Redwoods State Park: Just 9 miles from Healdsburg, this state park features majestic redwoods, scenic trails, and exciting outdoor adventures like hiking and biking amidst nature’s beauty.

Things to do recommended for couples

Healdsburg offers a perfect romantic getaway for couples. Savor exquisite wines at the Francis Ford Coppola Winery, enjoy thrilling water sports with Rubicon Adventures, or have fun at Pee Wee Golf and Arcade. These experiences create unforgettable memories in a charming setting.

Things to do recommended for families

Families visiting Healdsburg can indulge in sweet treats at Powell's Sweet Shoppe in nearby Windsor, offering a delightful atmosphere. For some fun on ice, the Redwood Empire Ice Arena promises sports and adventure, just a short drive away, ensuring memorable experiences for everyone.

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

When planning your trip—whether it's with a group, family, or pets, or if you're considering a longer stay—be sure to prioritize the right filters. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Healdsburg with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Healdsburg with young kids: Traveling with young kids can be quite a challenge. It’s important to prioritize their comfort and safety, along with having suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Healdsburg: For many families, a vacation wouldn’t feel complete without their beloved pets. If you can relate to this, consider exploring Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of your family 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 as well.

Where to stay near Healdsburg

Healdsburg, California, is a charming destination perfect for outdoor lovers and romantic getaways. Explore its scenic vineyards, historic downtown, and vibrant art scene. Nearby, you'll find family-friendly neighborhoods and sunny weather ideal for excursions. Whether you're seeking hillside vacation homes or unique vacation ideas, Healdsburg offers a relaxing atmosphere filled with friendly people. Make your next vacation unforgettable by immersing yourself in the beauty and culture of this delightful region.

  • Guerneville: Nestled about 10 miles from Healdsburg, Guerneville is a charming city known for its stunning outdoor experiences and vibrant natural scenery. This riverside gem is a favorite among adventure seekers, offering activities like kayaking along the Russian River and exploring the nearby Armstrong Redwoods State Natural Reserve. Visitors can indulge in rejuvenating spa treatments or relax at local recreational areas. Not to be missed are the picturesque beaches and lush landscapes that provide a perfect backdrop for a memorable getaway.
  • Windsor: Located just 5 miles from Healdsburg, Windsor is a delightful city that combines romance with outdoor enjoyment. The town boasts beautiful golf courses, making it an ideal spot for golf enthusiasts looking to play amidst scenic views. Windsor's charming piazza square offers a selection of dining and shopping options, perfect for a leisurely afternoon. With the nearby river and inviting beaches, visitors can bask in the beauty of the area while enjoying a variety of outdoor activities, making Windsor a lovely destination for couples and families alike.
  • Vacation Beach: Situated around 11 miles from Healdsburg, Vacation Beach is a picturesque village that promises adventure and relaxation. With its stunning boardwalk and amusement park, it’s a great spot for families looking for fun-filled activities. The nearby river and beach provide ample opportunities for swimming, sunbathing, and picnicking, while the proximity to national and state parks invites exploration of the great outdoors. Vacation Beach is a perfect destination for those seeking both excitement and a serene escape in a beautiful coastal setting.

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)SunnyAverageSlightly High
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)SunnyAverageAverage
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 hoping to cut costs on your upcoming trip? Being flexible with your travel dates can really make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and rental type. 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 booking. It truly pays off to be the organizer! By enrolling in our travel rewards program, One Key, you can immediately access member discounts and earn as well as redeem OneKeyCash™ on eligible reservations. Sign up today to begin enjoying the savings!

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform to plan new adventures, manage your travel arrangements, and keep your bookings organized. Your saved or reserved properties are categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please 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:

  • 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)
  • 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 most popular type of vacation rental accommodation in Healdsburg?
The most desirable types of vacation rentals in Healdsburg are cottages. After something a little different? Vrbo offers a variety of options to match our guests' unique needs, so you'll see properties in all sizes, and for all budgets. The perfect home away from home is waiting for you --- discover yours today.
How much does it cost to rent a vacation rental in Healdsburg?
Length of stay, property type and season are among the factors that can influence the price of a vacation home. Simply enter your dates of travel to find your perfect fit. From quaint country cottages to plush villas, all Vrbo vacation rentals provide unbeatable value.
How much does it cost to rent a beach house in Healdsburg?
When you travel and the style and size of the property will influence the cost of your beachside escape. Type in your Healdsburg travel dates to see all your options on Vrbo. Did someone just say "hot tub"? Use our filters to choose the amenities and features you want in your beach house.
Are there pet-friendly vacation rentals in Healdsburg?
Good news. There are. Choose from 61 stays that allow pets in Healdsburg on Vrbo. Our furry best friends need a getaway too, so simply use our search function for pet-friendly vacation rentals to find a perfect property where Fido can be near his favorite humans.
Can I rent a house with a pool in Healdsburg?
Add a whole new level of fun to your getaway by booking one of the 15 houses with a private pool in Healdsburg. Use our search filter to find properties with pools on Vrbo, then spend your days frolicking in a swimming pool that's exclusively for you.
What are popular rental amenities in Healdsburg?
A fireplace, a water view and a barbecue grill are rated the most popular rental amenities in Healdsburg. Whether you're traveling on your own, with your significant other or as a family group, Vrbo can help you find a vacation home that matches your style with all the options you need.
Are there large group vacation rentals in Healdsburg?
With two vacation rentals that can sleep 10 people or more in Healdsburg, there's no need to leave anyone off your invite list. From family vacations to events like anniversary parties and weddings, Vrbo can help you find a large group rental to suit the occasion.
Are there vacation rentals in Healdsburg that welcome kids?
With 61 family-friendly vacation homes to pick from in Healdsburg, now is a superb time to introduce the kids to the joys of travel. Simply check our "Properties good for families" filter to discover stays that come with amenities ideal for vacationing families, such as living rooms, pools, entertainment units and bunk beds.
What are the top attractions for families in Healdsburg?
Keeping the kids amused during your vacation in Healdsburg is easy with these cool family-friendly attractions:
  • Healdsburg Golf Club
  • Healdsburg Plaza
  • Jordan Vineyard & Winery

Are there one-bedroom vacation rentals in Healdsburg?
There are 11 one-bedroom properties in Healdsburg to pick from. A one-bedroom vacation rental is a superb choice if it's only you and your partner or if you're traveling alone. Toss in more convenience, space and privacy than a hotel, and you're sure to have an unforgettable getaway.
Can I find two-bedroom vacation rentals in Healdsburg?
You can select from 23 two-bedroom vacation homes in Healdsburg. Put your little ones in the second room or maybe fill it with a couple of your best buddies. There's space for whoever's fortunate enough to be joining your adventure.
Are there vacation rentals with WiFi in Healdsburg?
Healdsburg has 37 vacation rentals with WiFi, so you can stay connected during your vacation. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming Hollywood blockbusters to checking emails, these Vrbo homes make it easy to get online.
How can I find vacation rentals with air conditioning in Healdsburg?
Select your travel dates and then use the filter tool to locate vacation rentals with ac in Healdsburg on Vrbo. With 47 air-conditioned properties available, you can enjoy a comfy and cool stay.
How old do you have to be to rent a vacation rental in Healdsburg?
You should check with the Healdsburg vacation home you'd like on Vrbo as the minimum age differs. However, typically it's 16, 18 or 21.
How long can I rent a vacation rental in Healdsburg for?
The amount of time you can stay in a Healdsburg vacation rental for is up to each property. Just put in your travel dates to see options offering extended stays. They have all you need to make your extended trip more enjoyable and comfortable, such as kitchens and backyards. Some properties might also offer weekly or monthly discounted prices, so you can have a longer stay for less.
Does Vrbo offer discounts for vacation homes in Healdsburg?
On Vrbo, you'll find fantastic discounts and bargains for Healdsburg. Browse our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're planning a weekend getaway or an extended stay, Vrbo has lots of options for every style and budget.

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