Discover a selection of 500 vacation rentals in Healdsburg 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 WiFi. 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.
Reviews are in, families love these Healdsburg properties
Destination guide

A wine lover’s paradise in Sonoma

Sonoma is wine country, and if you’re thirsty to taste the best the area can offer, then Healdsburg is just the place. Famed for its quaint, small-town charm, Healdsburg is where you can spend days wandering artisan shops and meeting the friendly locals, in between glugging some of the best wines in California. Whether you’re hobnobbing with producers of local food, or chilling out on Healdsburg Veterans Memorial Beach by the Russian River, this is a community that’ll charm you into wanting to pack your belongings and move here for good.

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. If you're unable to find a flight that fits your schedule, you might consider flying into Novato, CA (NOT-Gnoss Field), which is 36.6 mi (59 km) away.

How many vacation rentals are available around Healdsburg?

Our 2021 property listings offer a large selection of 683 vacation rentals around Healdsburg. From 504 house rentals to 82 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.