0 Bedrooms for 1 Guest
Price $10 - $1000+

521 Healdsburg Holiday Rentals, Houses & Apartments

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Healdsburg holiday rentals from 9 rental sites including HomeAway, Booking.com, TripAdvisor, and more, ranging from $65 to $2800 a night. 
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    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 the perfect vacation rental for your Healdsburg getaway? Tripping.com’s got your trip covered. Whether you’re seeking a villa, cabin or cottage, Healdsburg offers 523 affordable homes to choose from, offering far more amenities, space and convenience than the average hotel room. Select from 363 properties with high-speed internet, 106 full with jacuzzi and pool, and NaN homes complete with outdoor patio well-suited for a barbecue with loved ones. Whatever your needs, find the perfect rental that best matches your accommodation style and budget.

    For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $8684 a month. Save hundreds with Tripping.com and even book instantly with properties marked “Instabook.” Healdsburg has 523 gorgeous homes with 137 pet-friendly rentals to choose from, perfect for your furry friends. Check out our listings now to get the latest deals, and book the right vacation rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com.

    Search properties from 9 rental sites in Healdsburg where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 292 HomeAway rentals, 121 Booking.com short term rentals and 64 TripAdvisor vacation rentals.