Healdsburg vacation rentals

We found 592 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Select from 144 homes, 24 cottages, and other vacation rentals in Healdsburg to find one that's 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.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

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:

  • 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)
  • Russian River Vineyard (10.1 mi / 16.2 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 popular types of vacation rentals in Healdsburg are houses. Looking for something different? Vrbo has numerous options to match our guests' diverse needs, so you'll see vacation 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 vacation rental in Healdsburg?

The average price for a vacation rental 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 traveling. All you have to do is enter your travel dates into Vrbo and how many guests to view vacation rental 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 vacation rentals in Healdsburg?

Yes. There are. Choose from 15 vacation rentals that welcome pets in Healdsburg on Vrbo. Our furry friends deserve a getaway too, so simply use our search function for pet-friendly vacation rentals 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 vacation homes and you'll enjoy pool days every day. Simply enter your dates into Vrbo, then check the "pool" filter to find the perfect place to make a splash!

What are popular rental amenities in Healdsburg?

Some of the most popular rental amenities people prefer in Healdsburg include mountain views, a chef and nearby museums. Whether you're vacationing with buddies, family or even pets, Vrbo vacation properties provide the best amenities for fun and relaxation with the people you love.

Are there large group vacation rentals in Healdsburg?

Take your pick of five Vrbo 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 vacation rentals in Healdsburg that welcome kids?

Healdsburg has 15 family-friendly vacation rentals to pick from. And tracking down a stay that welcomes youngsters is super easy with Vrbo'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 vacation 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 vacation rentals in Healdsburg?

Healdsburg has five one-bedroom rentals on offer. Often located in sought-after areas thanks to their smaller size, a one-bedroom vacation 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 vacation rentals in Healdsburg?

Gather your loved ones and relax in total privacy and comfort in one of the five two-bedroom vacation rentals Healdsburg has to offer.

Are there vacation rentals with WiFi in Healdsburg?

Take your pick of seven vacation rentals 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 Vrbo.

More Vacation Rentals ideas

People also search for