Healdsburg holiday lettings

We found 593 holiday rentals — enter your dates for availability

Discover a selection of 143 homes, 11 apartments and other holiday rentals in Healdsburg that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for spending time at your holiday home, including parking and a TV. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Healdsburg

Showing deals for:1 May - 8 May

Image gallery for Modern Retreat - Spectacular View Home Above Dry Creek Valley

Back of house/path to pool
9.4 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)

Modern Retreat - Spectacular View Home Above Dry Creek Valley

Healdsburg

8% off
Price is £8,773
for 7 nights, 1 home
£1,253 per night
includes taxes & fees
Modern Retreat - Spectacular View Home Above Dry Creek Valley

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Arty Healdsburg will entice you

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

Activities and attractions in and around Healdsburg

Are you hoping to find attractions to visit during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Healdsburg a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Wilson Winery (2.6 mi / 4.2 km)
  • Jordan Vineyard & Winery (3.4 mi / 5.5 km)
  • SingleThread Farm at Dry Creek (3.5 mi / 5.7 km)
  • Dry Creek Vineyard (4.2 mi / 6.8 km)
  • Francis Ford Coppola Winery (4.9 mi / 7.9 km)
  • Windsor Golf Club (6.7 mi / 10.8 km)

Exploring the natural landscape of Healdsburg

Whether you're looking for adventure or just want to take in the scenery, Healdsburg is a great place to spend some time outside. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Travelling 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 centre.

Frequently asked questions

What is the best area to stay in Healdsburg when booking a holiday rental?
When considering a holiday rental in Healdsburg, a popular area to stay is the charming downtown district. This vibrant area is brimming with boutique shops, art galleries, and an array of delightful restaurants, making it ideal for those who appreciate a lively atmosphere. A popular attraction nearby is the Healdsburg Plaza, a picturesque square often bustling with events and local markets. Visitors can enjoy leisurely strolls, sample local wines at nearby tasting rooms, and experience the town's warm community spirit.

Another excellent option is the Russian River area, which offers a more tranquil setting while still being close to the heart of Healdsburg. This region is great for those who enjoy outdoor activities, with opportunities for kayaking, hiking, and cycling along the scenic riverbanks. The natural beauty of the area is complemented by the nearby Armstrong Redwoods State Natural Reserve, where you can marvel at towering ancient redwoods in a serene environment.
How much does it cost to rent a holiday home in Healdsburg?
Prices for holiday rentals in Healdsburg vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Healdsburg to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Healdsburg holiday house rentals?
You can find great discounts on house rentals in Healdsburg on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Healdsburg?
For renting a beach house in Healdsburg, California, travellers may want to consider the nearby coastal areas of Sonoma County, particularly around Bodega Bay and Jenner. These locations offer a picturesque setting along the Pacific coast, with beach houses often featuring stunning ocean views, spacious decks for outdoor dining, and easy access to sandy beaches. Many properties come with amenities such as fully equipped kitchens, barbeque facilities, and cosy fireplaces, great for family gatherings or romantic getaways.

Bodega Bay is well-known for its charming waterfront and seafood restaurants, making it an ideal spot for those looking to enjoy fresh local cuisine. Beach houses in this area often provide access to nearby hiking trails in the Sonoma Coast State Park, where travellers can experience breathtaking vistas and explore rugged coastal landscapes.

Further north, Jenner presents a more tranquil atmosphere, with rental properties that might include private access to the beach and direct views of the Russian River meeting the ocean. Many of these homes feature modern amenities, such as hot tubs and outdoor fire pits, allowing guests to unwind after a day of exploration.
What is the most popular type of holiday rental accomodation in Healdsburg?
In Healdsburg, holiday houses are the most popular type of accommodation, with about 120 available throughout the area. These properties are typically located in picturesque neighbourhoods, providing easy access to local wineries and the charming downtown area. Most holiday houses come equipped with spacious living areas, fully stocked kitchens, and outdoor spaces for enjoying the lovely California weather.
Are there any family house rentals in Healdsburg?
In Healdsburg, there is a wealth of family-friendly holiday rentals available, with around 117 options throughout the area. The charming town is renowned for its beautiful vineyards and scenic countryside, making it an excellent destination for families looking to enjoy a relaxing getaway.

Properties in this locale typically offer spacious living areas, full kitchens for preparing family meals, and outdoor spaces superb for children to play. Many homes come equipped with amenities such as air conditioning and Wi-Fi, ensuring a comfortable stay for all ages.
Can I rent a holiday home with a pool or hot tub in Healdsburg?
In Healdsburg, there are plenty of holiday homes available for rent that come with pools and hot tubs, with around 68 options to choose from. This picturesque town, located in the heart of Sonoma County's wine country, is known for its charming downtown area and beautiful vineyards. Many of the rentals in Healdsburg feature private pools, inviting hot tubs, and expansive outdoor spaces, superb for relaxation and entertaining.
Can I find long-stay holiday rentals in Healdsburg?
A long-stay holiday rental in Healdsburg is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Healdsburg?
In Healdsburg, there are numerous pet-friendly house rentals available, providing a warm welcome for travellers with furry companions. Many of these properties are situated in the scenic wine country, where guests can enjoy the beautiful landscapes and vineyard views. Expect amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, superb for families or groups seeking relaxation.

The charm of Healdsburg extends beyond the rentals themselves, as the town features several parks and open spaces where pets are welcome. For example, Healdsburg Memorial Beach offers a great spot for leisurely strolls along the riverbank, and parks like Plaza Park provide a lovely setting for picnics with your pet. Additionally, the area is home to various pet-friendly wineries, allowing visitors to enjoy wine tastings while their pets accompany them.
Are there any remote work holiday rentals in Healdsburg?
In Healdsburg, there is an impressive selection of remote work holiday rentals, with around 152 options available. This charming town, located in California's wine country, offers a delightful blend of relaxation and productivity for those working remotely. Many properties come equipped with amenities tailored for remote workers, including high-speed Wi-Fi, dedicated office spaces, and comfortable desk setups, such as desk chairs and monitors.

Travellers can expect a variety of accommodations, from spacious homes with multiple bedrooms to cosy cottages, all designed to provide a conducive environment for work. Additionally, many rentals feature outdoor spaces where guests can unwind after a day of meetings, along with fully equipped kitchens for convenient meal preparation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Healdsburg holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Healdsburg with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Healdsburg?
In Healdsburg, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with ease. Many properties feature patios where visitors can relax outdoors and enjoy the pleasant Californian weather. Additionally, travellers can expect essential cookware, dishware, and utensils, along with modern appliances like microwaves and ovens, making it convenient for those who prefer a home-cooked experience during their stay.
When is the best time to visit Healdsburg for a holiday rental?
The most popular time to visit Healdsburg for a holiday rental is in October, when the vineyards are in full harvest mode and the region comes alive with vibrant autumn colours. This month provides a delightful backdrop for wine enthusiasts looking to explore the world-class wineries that the area is famous for. With average temperatures hovering around the mid-teens to low 20s Celsius, visitors can comfortably enjoy outdoor tastings, picturesque strolls through the charming town, and various local events celebrating the grape harvest.

The peak season spans from August to October, attracting tourists eager to partake in the wine-tasting experiences and seasonal festivals. During this time, you'll find a bustling energy in Healdsburg, with many activities available, including artisanal food markets and outdoor concerts.

For those looking for a more budget-friendly option, December offers a quieter alternative with the festive charm of the holiday season. While temperatures can dip to around 7°C, the reduced crowds allow for a more intimate experience of the local culture and cosy moments in the town's cafés and restaurants. Plus, the winter months provide a unique opportunity to appreciate the region's beauty devoid of the busier tourist traffic.
How early should I book a Healdsburg holiday rental?
Book your Healdsburg holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Healdsburg?
In Healdsburg, visitors can experience firsthand a rich array of attractions that highlight the region's charm and natural beauty. The town square is the heart of the community, surrounded by boutique shops, art galleries, and delightful restaurants that showcase local cuisine and wines from the surrounding vineyards.

Wine enthusiasts will appreciate the nearby wineries in the Russian River Valley, where many tasting rooms welcome guests to sample renowned varietals. The picturesque landscapes of vineyards, rolling hills, and the beautiful scenery along the Russian River provide plenty of opportunities for outdoor activities, including kayaking and biking.
Can I change or cancel my Healdsburg home rental booking on Vrbo?
To find Healdsburg holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Healdsburg holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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