Healdsburg holiday lettings

We found 591 holiday rentals — enter your dates for availability

Discover a selection of 140 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:3 Jul - 10 Jul

Image gallery for Santini Farmhouse with Tastings Included

Miscellaneous
10 out of 10, Exceptional, (55 reviews)
Exceptional
(55 reviews)

Santini Farmhouse with Tastings Included

Healdsburg

7% off
Price is £4,194
for 7 nights, 1 cottage
£599 per night
includes taxes & fees
Santini Farmhouse with Tastings Included

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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:

  • Jordan Vineyard & Winery (3.4 mi / 5.5 km)
  • Ridge Vineyards - Lytton Springs (3.5 mi / 5.6 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)
  • Korbel Winery (8.8 mi / 14.1 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 neighbourhood is known for its delightful blend of boutique shops, art galleries, and an impressive array of dining options, making it a great spot for those who wish to immerse themselves in local culture. The central plaza is particularly noteworthy, often serving as the heart of the community with its beautiful gardens and regular events.

Additionally, the surrounding areas such as the Russian River offer a more tranquil setting, ideal for those looking to unwind amidst nature. This region features lovely parks and opportunities for outdoor activities, including kayaking and hiking.

In terms of properties, downtown Healdsburg boasts a diverse selection, ranging from quaint cottages to luxurious homes, suiting various preferences and group sizes. Not far from the downtown area, you can also explore the renowned wineries that make this region famous, adding a touch of adventure and flavour to your stay.
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, travellers should consider the nearby Russian River area, which offers a delightful blend of riverfront and wooded settings. The stretch along the river, particularly near the towns of Guerneville and Monte Rio, features properties that provide a serene escape with easy access to sandy banks and swimming spots. Many of these holiday homes come equipped with amenities such as outdoor decks, barbecues, and spacious living areas, great for families or groups looking to enjoy a riverside retreat.

Additionally, the coastal town of Jenner, located slightly further afield at the mouth of the Russian River, offers stunning ocean views and charming beach houses. Here, visitors can expect properties that often include large windows for breathtaking scenery, hot tubs, and proximity to local beaches such as Goat Rock State Beach. The area is also known for its natural beauty and opportunities for wildlife observation, making it an excellent choice for nature enthusiasts.

While Healdsburg itself is renowned for its vineyards and wine culture, the nearby coastline and river provide an appealing mix of relaxation and outdoor activities, including kayaking, hiking, and exploring the scenic beauty of Sonoma County.
What is the most popular type of holiday rental accomodation in Healdsburg?
In Healdsburg, holiday houses are the most popular type of holiday rental, with around 472 available throughout the area. These properties are often situated in picturesque neighbourhoods, close to local wineries and the charming town centre, making them ideal for those looking to explore the region's renowned wine culture. Most holiday houses come equipped with spacious living areas, fully stocked kitchens, and outdoor spaces such as patios or gardens for enjoying the beautiful Californian weather.

Additionally, there are about 72 cottages that offer a quaint and cozy experience, superb for couples or small families. These usually feature rustic decor, kitchen facilities, and often a fire pit for evening gatherings. For those seeking more compact options, approximately 40 apartments provide a convenient base for exploring Healdsburg, typically including kitchen amenities and comfortable seating areas.

While villas and condos are less common, with 16 and 12 available respectively, they still present unique options for visitors looking for a more upscale experience.
Are there any family house rentals in Healdsburg?
In Healdsburg, California, there are numerous family-friendly house rentals available, with around 110 options throughout the area. Visitors can find homes in charming neighbourhoods such as the historic downtown or the picturesque outskirts, each offering great experiences. Many properties feature spacious living areas, full kitchens equipped for family meals, and outdoor spaces that may include pools or gardens, superb for children to play in.

Additionally, these rentals are conveniently located near local attractions, such as the Healdsburg Plaza, where families can enjoy farmer's markets and various dining options. The nearby Russian River also provides opportunities for outdoor activities like kayaking and picnicking.
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 feature pools and hot tubs, with around 64 options to choose from. This picturesque town, located in California's renowned wine country, offers a variety of charming neighbourhoods where these properties can be found, including the scenic Dry Creek Valley and the vibrant downtown area.

Travellers can expect a range of amenities in these rentals, such as private swimming pools, inviting hot tubs, outdoor dining areas, and fully equipped kitchens, making them superb for both relaxation and entertaining. Many properties also feature lush gardens, patios, and sometimes even vineyard views, enhancing the overall holiday experience.
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, with around 71 options for travellers seeking a welcoming environment for their furry friends. Many of these holiday homes feature spacious layouts, fully equipped kitchens, and outdoor areas such as patios or gardens where pets can enjoy the fresh air.

The charming downtown area of Healdsburg offers a vibrant setting with boutique shops, restaurants, and wine tasting rooms, all within a short distance from many of these rentals. Additionally, the nearby Healdsburg Plaza provides a lovely park setting, superb for leisurely strolls with pets, while the surrounding wine country offers opportunities for scenic hikes and exploration of dog-friendly vineyards.
Are there any remote work holiday rentals in Healdsburg?
In Healdsburg, California, there is an abundance of remote work-friendly holiday rentals available, with around 584 options to choose from. This charming wine country town is not only known for its picturesque vineyards and culinary delights but also offers a conducive environment for remote work. Many properties come equipped with high-speed Wi-Fi, dedicated workspaces including desks and chairs, and comfortable living areas that allow for a seamless blend of work and relaxation.

Travellers can expect to find amenities such as fully equipped kitchens, outdoor spaces for fresh air breaks, and cozy lounges for unwinding after a productive day. The town's vibrant centre, with its boutique shops, tasting rooms, and restaurants, provides ample opportunities to explore during downtime. 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 kitchens, allowing guests to prepare their own meals with local ingredients from nearby markets. Many rentals also feature decks or patios, providing a lovely outdoor space to enjoy the scenic views of vineyards and surrounding countryside. Onsite parking is commonly available, making it convenient for travellers with cars. Additionally, many properties come equipped with coffee and tea makers, ensuring guests can start their day with a warm beverage.
When is the best time to visit Healdsburg for a holiday rental?
The best time to visit Healdsburg for a holiday rental is during the vibrant months of August to October, with October being particularly popular among travellers. This season captures the essence of the California wine country, as vineyards burst with colour and offer a lot of harvest events, making it an ideal time for wine enthusiasts and those seeking a relaxed yet engaging getaway.

In October, temperatures typically range between 10 to 25 degrees Celsius, creating a pleasant climate for outdoor activities such as wine tasting tours, leisurely strolls through the picturesque downtown, and even cycling along scenic routes. The combination of comfortable weather and stunning autumn foliage enhances the overall experience, allowing visitors to fully immerse themselves in the beauty of the region.

For those looking to save a bit on accommodation, December presents a quieter alternative. While the holiday season can still be charming, it's an excellent time for travellers seeking a peaceful retreat amid the festive decorations, without the bustling crowds.
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 take part in a charming blend of wine country attractions and natural beauty. The town square is a focal point, featuring quaint shops, art galleries, and delightful eateries that showcase local cuisine. Just a short stroll away, the Russian River offers opportunities for kayaking and fishing, making it a popular spot for outdoor enthusiasts.

For wine lovers, the surrounding vineyards are a significant draw, with many wineries offering tastings and tours. Notable areas include Dry Creek Valley and Alexander Valley, where visitors can explore picturesque estates and sample a variety of exquisite wines.

Additionally, the Healdsburg Plaza hosts events and farmers' markets, fostering a vibrant community atmosphere.
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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