51 Healdsburg Vacation Rentals & Short Term Rentals

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Compare Healdsburg vacation rentals from 5 rental sites including HomeAway, Booking.com, HRS Holidays and more, ranging from $84 to $3122 a night.

Information about Healdsburg

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.

Vacation Rentals in Healdsburg

Looking for a vacation rental in Healdsburg? Tripping.com has 52 rental homes available in Healdsburg. Potential renters will find 0 studios, 33 1-bedroom, 7 2-bedroom and 12 rentals with 3 or more bedrooms ranging from $84 a night to $3122 a night. Many of these properties are instantly bookable.

The average price of a nightly rental in Healdsburg is $697 while the average price of a weekly rental is $1519. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Healdsburg home is $6510.

Wondering if you can bring your favorite dog or cat with you? We have 10 pet friendly vacation rentals available for you. In addition to accommodating pets, Healdsburg rentals offer a variety of amenities. In particular, 42 rentals have internet and wifi, 32 have TV and/or cable and 19 have a pool or hot tub.

Search properties from 5 rental sites in Healdsburg where the top providers in that area are HomeAway, Booking.com, and HRS Holidays. There are 22 HomeAway rentals, 17 Booking.com short term rentals and 7 HRS Holidays vacation rentals.