Healdsburg vacation rentals

We found 578 vacation rentals — enter your dates for availability

your current months are October, 2023 and November, 2023.
October 2023
November 2023
Select from 143 homes, 21 cottages, and other vacation rentals in Healdsburg to find one that's perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the best amenities for hanging out with the people that matter most, which might include WiFi and a pool. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

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Artsy Healdsburg will entice you

The area's wineries and art galleries are just a few of the reasons to vacation in Healdsburg. Well known for its restaurants, riverfront and shopping, this walkable city won't disappoint. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Healdsburg

Are you searching for attractions to visit in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Healdsburg a fun place to get away. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Jordan Vineyard & Winery (3.4 mi / 5.5 km)
  • Dry Creek Vineyard (4.2 mi / 6.8 km)
  • Francis Ford Coppola Winery (4.9 mi / 7.9 km)
  • Trentadue Winery (4.9 mi / 7.9 km)
  • Korbel Winery (8.8 mi / 14.1 km)
  • Kendall-Jackson Wine Estate and Gardens (9.1 mi / 14.6 km)

Exploring the natural landscape of Healdsburg

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Healdsburg is a great place to spend some time outside. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Russian River (4.4 mi / 7 km)
  • Armstrong Redwoods State Park (9 mi / 14.5 km)
  • Kendall-Jackson Wine Estate and Gardens (9.1 mi / 14.6 km)
  • Safari West (10.1 mi / 16.3 km)
  • Johnson's Beach (10.3 mi / 16.6 km)
  • Lake Sonoma (10.9 mi / 17.6 km)

Traveling to and around Healdsburg

The nearest airport is in Santa Rosa, CA (STS-Sonoma County), located 7.7 mi (12.5 km) from the city center.

Frequently asked questions

How many vacation rentals are in Healdsburg?

Our current selection of vacation homes in Healdsburg is ${propertiesCount}. All it takes is a simple Vrbo property search to book your next cottage, villa, condo or whatever type of vacation rental that suits your needs.

What is the most popular type of vacation rental accommodation in Healdsburg?

Based on our research, houses are the most desirable type of property in Healdsburg. But as you know, everyone's idea of the perfect stay isn't the same. Vrbo has vacation homes in a variety of sizes and shapes, and we'll help you locate your ideal fit.

How much does it cost to rent a vacation rental in Healdsburg?

Property type, season and length of stay are some of the things that can affect the price of a vacation home. Simply add your travel dates to find your perfect fit. From comfy cabins to expansive luxury villas, all Vrbo vacation rentals offer amazing value.

How much does it cost to rent a beach house in Healdsburg?

When you travel and the style and size of the property will help determine the cost of your beachside escape. Type in your Healdsburg travel dates to view your options on Vrbo. Can't live without a hot tub? Use our filters to choose the amenities and features you want in your beach house.

Are there pet-friendly vacation rentals in Healdsburg?

Yes. You'll have a choice of 15 vacation rentals that allow pets in Healdsburg. Plenty of our pet-friendly vacation rentals have an outdoor space for your furry pal to run around in, complimentary treats, special dog beds and proximity to parks or green space. Apply the 'Pets allowed' filter to find your place on Vrbo.

Can I rent a house with a pool in Healdsburg?

Dig out your swimsuit and inflatable unicorn, because there are three houses with a private pool in Healdsburg. Stay at one of these popular vacation rentals and every day can be a pool day. Simply enter your dates into Vrbo, then check the 'pool' filter to find a place to make a splash!

What are popular rental amenities in Healdsburg?

Beach sun loungers, nearby museums and a fireplace rank as the most popular rental amenities in Healdsburg. Whether you're traveling on your own, with a partner or a bunch of friends, Vrbo will help you find a vacation rental that matches your style with a load of extras you'll love.

Are there large group vacation rentals in Healdsburg?

Yes, you can pick from one of five vacation rentals in Healdsburg that can host a group of five or more guests. From family getaways to special occasions, these stays have ample room to kick back with the people that matter the most.

Are there vacation rentals in Healdsburg that welcome kids?

Gather your whole family for a fun-packed adventure in Healdsburg at one of our 15 family-friendly vacation rentals. These stays feature conveniences that are great for trips with youngsters, including laundry facilities, living rooms and patios. Just click on the "Properties good for families" filter and pick your favorite option.

What are the top attractions for families in Healdsburg?

Keep the kids busy at these fabulous family-friendly attractions in Healdsburg:

  • Pacific Coast Air Museum
  • Armstrong Redwoods State Park
  • Healdsburg Center for the Arts

Are there one-bedroom vacation rentals in Healdsburg?

You can pick from five one-bedroom rentals in Healdsburg. Whether you're looking for a cozy cottage or an upmarket condo, our one-bedroom properties are great if you don't require a lot of space. One of the perks of having your own digs? You'll never have to share your getaway with strangers.

Can I find two-bedroom vacation rentals in Healdsburg?

Gather your loved ones and enjoy peace, privacy and comfort in one of the five two-bedroom vacation rentals Healdsburg has to offer.

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