Find Vacation Rentals in Healdsburg

We have 459 properties to choose from
Healdsburg
Anytime
Guests

Popular Healdsburg Vacation Rentals

Find the perfect Healdsburg vacation rental

House Healdsburg
$556 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
"Excellent" (4 ratings)
Healdsburg, Sonoma County, California, United States
Details
Vrbo
Details
Details
House Healdsburg
$188 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (14 ratings)
Healdsburg, Sonoma County, California, United States
Details
Vrbo
Details
Details
House Healdsburg
$568 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (234 ratings)
Healdsburg, Sonoma County, California, United States
Details
Vrbo
Details
Details
House Healdsburg
$911 per night
House ∙ 8 guests ∙ 3 bedrooms
4.8
"Excellent" (29 ratings)
Healdsburg, Sonoma County, California, United States
Details
Vrbo
Details
Details
House Healdsburg
$481 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (108 ratings)
Healdsburg, Sonoma County, California, United States
Details
Vrbo
Details
Details
House Healdsburg
$312 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (311 ratings)
Healdsburg, Sonoma County, California, United States
Details
Vrbo
Details
Details
Cottage Healdsburg
$194 per night
Cottage ∙ 2 guests ∙ 1 bedroom
4.9
"Excellent" (107 ratings)
Healdsburg, Sonoma County, California, United States
Details
Vrbo
Details
Details
Apartment Healdsburg
$105 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0
"Excellent" (10 ratings)
Healdsburg, Sonoma County, California, United States
Details
Vrbo
Details
Details
House Healdsburg
$281 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (14 ratings)
Healdsburg, Sonoma County, California, United States
Details
Vrbo
Details
Details
View more

Cabins and Homes With Fireplaces

House Fireplace Healdsburg
$551 per night
House ∙ 4 guests ∙ 3 bedrooms
4.7
"Outstanding" (25 ratings)
Healdsburg, Sonoma County, California, United States
Fireplace
Details
Vrbo
Details
Details
House Fireplace Healdsburg
$1,161 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
"Excellent" (99 ratings)
Healdsburg, Sonoma County, California, United States
Fireplace
Details
Vrbo
Details
Details
Cottage Fireplace Healdsburg
$334 per night
Cottage ∙ 2 guests ∙ 1 bedroom
4.9
"Excellent" (148 ratings)
Healdsburg, Sonoma County, California, United States
Fireplace
Details
Vrbo
Details
Details
View more

Vacation Homes With Terraces

House Balcony/Patio Healdsburg
$236 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (114 ratings)
Healdsburg, Sonoma County, California, United States
Balcony/Patio
Details
Vrbo
Details
Details
Villa Balcony/Patio Healdsburg
$487 per night
Villa ∙ 6 guests ∙ 2 bedrooms
4.5
"Outstanding" (22 ratings)
Healdsburg, Sonoma County, California, United States
Balcony/Patio
Details
Vrbo
Details
Details
House Balcony/Patio Healdsburg
$233 per night
House ∙ 4 guests ∙ 2 bedrooms
4.6
"Outstanding" (9 ratings)
Healdsburg, Sonoma County, California, United States
Balcony/Patio
Details
Vrbo
Details
Details
View more

Vacation homes and rentals with a yard

House Yard Healdsburg
$271 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (4 ratings)
Healdsburg, Sonoma County, California, United States
Yard
Details
Vrbo
Details
Details
House Yard Healdsburg
$189 per night
House ∙ 5 guests ∙ 2 bedrooms
5.0
"Excellent" (1 rating)
Healdsburg, Sonoma County, California, United States
Yard
Details
Vrbo
Details
Details
Cottage Yard Healdsburg
$263 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (1 rating)
Healdsburg, Sonoma County, California, United States
Yard
Details
Vrbo
Details
Details
View more

Frequently Asked Questions

Is renting a vacation home in Healdsburg expensive?

You can book a vacation rental in Healdsburg for as little as $105 per night.

Are there any vacation rentals available to book in Healdsburg?

There are 459 vacation rental offers in Healdsburg available to book.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Healdsburg Information

About Healdsburg

Healdsburg is located in Sonoma County north of the San Francisco Bay Area. It's a quaint, but beautiful town that used to be an agricultural outpost. The three main areas of interest are the town plaza with lovely boutiques, restaurants and Bed and Breakfasts; the Russian River, and the wineries along Westside Road and Dry Creek Road.

Things to do in Healdsburg

Healdsburg is in Sonoma County, which means that the wine is the main attraction that draws visitors to Healdsburg. You are guaranteed to enjoy some great wine while you’re visiting Healdsburg, and there are a number of great wineries and vineyards worth visiting. Dry Creek Vineyard is the most popular vineyard in Healdsburg, and was founded in 1972. It’s a beautiful family-owned vineyard that covers over 150 acres and offers delicious wine tasting and tours. Some of the other top-rated wineries in Healdsburg include Gracianna Winery, Jordan Vineyard and Winery, and Ferrari-Carano Winery, among dozens of others. Another fun activity in the area is to go kayaking or canoeing on the Russian River. You can easily do this with River’s Edge Kayak and Canoe Trips. The Russian River has a few very small twists and turns and eventually leads to the Pacific Ocean. Plan to spend a half-day on the water, and bring a picnic! You can also rent a bike from Wine Country Bikes and take a ride in the beautiful Dry Creek or Russian River Valleys.

Day trips from Healdsburg

Healdsburg is in an ideal location for scenic day trips. If you’re on a wine trip of the area, be sure to explore the Napa Valley and take an hour drive to Napa, California, where you can visit some of the world’s best wineries. There are countless wineries to tour in the area, so plan ahead and choose which ones you want to visit. Be sure to visit the town of Sonoma as well, with a different wine-tasting atmosphere and a charming town center. If you’re looking to get out of wine country for an afternoon or night, you can take a trip to the city of San Francisco. It’s one of the most popular tourist cities in America thanks to the Golden Gate Bridge and its many other attractions like Alcatraz, the Palace of Fine Arts, Golden Gate park and more. San Francisco also has major sports teams like the San Francisco Giants who play in the beautiful AT&T Park and the Golden State Warriors basketball team across the bay in Oakland.

Healdsburg Accommodations

There are great vacation rentals in the Healdsburg area that give great views of wine country or offer a view of the beautiful Russian River. Stay anywhere off of Dry Creek Road and you’ll likely be near some great wineries and vineyards. Rentals off of Vine Street or North Street will put you in close proximity to the downtown Town Plaza district. Anywhere off of Westside Road is also a great place to stay as well where you’ll likely be near vineyards.

Transportation in Healdsburg

You should plan to have a vehicle when in Healdsburg, whether you drive your own or rent one, so you can get around to the various wineries and surrounding areas. There are also limo shuttle services in Healdsburg that will take you around the wine country area. This is a good idea if you’re with a group of friends or are planning to visit multiple wineries and would rather not drive. Alternatively, you can bike around and walk the downtown area.

Popular Day Trips Near Healdsburg

Show more
image-tag