Discover a selection of 417 vacation rentals in Healdsburg, CA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $185 per night, and houses and cottages are popular options for a stay in Healdsburg. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Healdsburg
Things to do

Wine tasting in Healdsburg

When it comes to attractions in Healdsburg, it’s all about the wine. After all, this community is surrounded on all sides by some of California’s most celebrated appellations, from Dry Creek Valley to Chalk Hill. You’ll want to seek out the many tasting rooms in Healdsburg itself, while serious wine buffs should also make time to visit the vineyards which sprawl for many 1000s of acres. From grand, ornate, European-style villas to smaller, family-owned wineries with an equal passion for excellence, there’s plenty for the thirsty oenophile to explore. Another, quirky attraction is the Hand Fan Museum, which houses over 2,500 fans from across several centuries.


Blissful browsing in Healdsburg

Browsing and shopping has to come right at the top of any traveler to-do list in Healdsburg. The lanes are dotted with cozy boutiques, galleries, and grottos filled with antiques, ceramic figurines, and colorful, locally crafted jewelry. Even if you don’t intend to buy anything, it’s the perfect way to while away the hours on a sunny day, while you can refuel at one of the many independently-owned eateries serving up organic, farm-to-table dishes that will excite the most fervent foodies. Afterwards, head over to Healdsburg Veterans Memorial Beach, or try kayaking down the rippling waters of the Russian River.


All-year-round escapes in Healdsburg

Pondering when to book your Healdsburg vacation rental? If you’re after sun-dappled, golden-green, picture-postcard perfection, then early summer is ideal. The weather will bring out the beauty of the rolling hills, and the streets will buzz with fellow browsers and wine-worshippers. Speaking of wine, you may also want to consider coming during the grape harvest in September and October. On the other hand, if peace and serenity are your thing, try a Healdsburg vacation rental in the winter, when you certainly won’t have to jostle for position in the quiet tasting rooms, and you won’t have to book the best restaurants far in advance.

Natural features

Outdoorsy adventures in Healdsburg

The area around Healdsburg has been compared to Tuscany, which should give you an idea of how idyllic it all is. Think emerald rows of immaculate vines across undulating hills, towering redwood trees, and the curving course of the Russian River. It’s no wonder the area is a favorite with outdoorsy types, attracting those with a love of steelhead fishing. If you’re here with the whole family, you can take in the beauty of the landscape by taking an inflatable canoe along the river. Or, if heights don’t faze you, why not take a hot air balloon ride over this rolling landscape, and take in the majesty of the sunset.

How to get there

Traveling to and around Healdsburg

The nearest airport is in Santa Rosa, CA (STS-Sonoma County), located 7.8 mi (12.6 km) from the city center.

How many vacation rentals are available around Healdsburg, CA?

Our 2022 property listings offer a large selection of 417 vacation rentals around Healdsburg. From 292 house rentals to 41 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Healdsburg?

Vrbo offers a large selection of vacation rentals near lovely places in Healdsburg. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Healdsburg Plaza: 257 vacation rentals
  • Pezzi King Winery: 848 vacation rentals
  • Dry Creek Vineyard: 528 vacation rentals
  • Chalk Hill Estate Vineyard: 1,000 vacation rentals
  • Wilson Winery: 813 vacation rentals

But there are many other points of interest around Healdsburg listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Healdsburg?

Yes, of course. Vrbo has 292 Houses in Healdsburg. Our other popular types of vacation rentals in Healdsburg include:

  • Cottages: 41 rentals available
  • Cabins: 41 rentals available
  • Villas: 10 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Healdsburg?

Yes, you can select your preferred vacation rental with pool among our 191 vacation rentals with pool available in Healdsburg. Please use our search bar to access the selection of vacation rentals available.