Vacation Rentals in Healdsburg, CA

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Healdsburg, CA holiday rentals
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162 Holiday rentals and Airbnb in Healdsburg, CA

Top-Rated Family-Friendly Holiday Rentals in Healdsburg, CA, United States

Keep the whole group together under one roof with plenty of space to lounge at family holiday rentals in Healdsburg, CA, United States.

Modern Wine Country Home On 10 Acres With Vineyard - Healdsburg, CA
No reviews

Modern Wine Country Home On 10 Acres With Vineyard

house, Healdsburg
This three-bedroom Healdsburg villa is situated 8km from Healdsburg Plaza and 19km from Charles M. Schulz Sonoma County Airport, offering easy access to local amenities and attractions.
The 4-hectare property, boasting a vineyard and stunning views, includes a fully equipped kitchen, two bathrooms, and accommodates up to 11 guests, with amenities such as Wi-Fi, a fireplace, and private parking; nearby attractions include Robert Louis Stevenson State Park (48km), Safari West (38km), and Petrified Forest (40km).
Spectacular Healdsburg Manor-4br/4.5ba, Pool+2 Spa! - Healdsburg, CA
9.4 12 reviews

Spectacular Healdsburg Manor-4br/4.5ba, Pool+2 Spa!

apartment, Healdsburg
This Healdsburg mountainside property is situated within 3.2km of Ridge Vineyards, Mazzocco Winery, and Simi Winery, and 4.8km from the Krug Event Center.
This six-bedroom, six-bathroom house boasts 288 square metres of living space, a private pool, jacuzzi, and game room, accommodating up to ten guests and offering self-catering facilities.
Large Outdoor Kitchen, Pool, Hot Tub, Firepit...8 Mins From Healdsburg Plaza - Healdsburg, CA
10 222 reviews

Large Outdoor Kitchen, Pool, Hot Tub, Firepit...8 Mins From Healdsburg Plaza

apartment, Healdsburg
This family-friendly house is located on a river in Healdsburg, within a 3km radius of Jordan Vineyard & Winery and Medlock Ames Winery, and within 5km of Russian River and Simi Winery. The house has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The property spans 260 square metres and comfortably accommodates up to 8 guests. Enjoy a range of amenities including a private pool, fitness centre, spa tub, barbecue grills, and a fully equipped kitchen, making it perfect for a relaxing and enjoyable stay.
Farm Stay Villa On 55 Acres // Pool, Hot Tub & Complimentary Wine Tasting - Healdsburg, CA
10 80 reviews

Farm Stay Villa On 55 Acres // Pool, Hot Tub & Complimentary Wine Tasting

apartment, Healdsburg
This luxurious villa is situated in the Dry Creek Valley, just 16 kilometres from Healdsburg town centre and a kilometre past the Dry Creek General Store, offering a peaceful escape in the heart of the wine country. The property has received excellent reviews from previous guests, highlighting its unique charm and exceptional service.
This spacious four-bedroom villa, spanning 316 square metres, comfortably accommodates eight guests. It features a range of amenities, including a private swimming pool, a hot tub, a fully equipped kitchen, and a garden, perfect for relaxing and enjoying the stunning views of the Dry Creek Valley.

Best Healdsburg, CA holiday rentals with parking

Heron House - Hot Tub And Wine Tastings Included - Healdsburg, CA
9.9 102 reviews

Heron House - Hot Tub And Wine Tastings Included

house, Healdsburg
This charming cottage is situated just 0.16 kilometres from the Russian River and within 5 kilometres of Healdsburg's main attractions, including the hospital, golf club, museum and arts centre. The cottage enjoys excellent user, location and cleanliness ratings.
The 102 square metre property has three bedrooms and two bathrooms, and offers a range of amenities to ensure a comfortable stay. Guests can enjoy the on-site spa, tennis court, garden and barbecue, as well as access to the beach.
The Wine Ranch - Healdsburg, CA
9.9 301 reviews

The Wine Ranch

apartment, Healdsburg
This traditional ranch-style house is located just north of the Healdsburg Plaza, a short 5-minute drive from the Montage Healdsburg, putting you within easy reach of the town's restaurants, shops, and events. This property has received excellent ratings for its location, cleanliness, and overall experience.
The house has three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Guests can enjoy a range of amenities, including a bocce court, a deck, and a patio, offering ample space for outdoor relaxation and entertainment.
Dry Creek Modern - Healdsburg, CA
10 31 reviews

Dry Creek Modern

apartment, Healdsburg
Apartment rental for up to 6 people with an excellent rating of 100% based on 31 reviews. You will be located in Healdsburg.
Services and facilities include a garden, a sauna and a dish washer. This apartment is ideal for families.
Wine Country Cottage Walkable To River Or Downtown - Healdsburg, CA
9.9 205 reviews

Wine Country Cottage Walkable To River Or Downtown

apartment, Healdsburg
This two-bedroom flat is conveniently located just 800 metres from Healdsburg's town centre, within easy walking distance of numerous wineries and the Russian River. The property consistently receives excellent ratings for cleanliness, location and user experience.
The flat is ideal for families or groups of up to four people. Guests can enjoy a range of amenities including a fully equipped outdoor kitchen, a private deck with a fireplace and a projector, and access to standup paddleboards and float tubes for exploring the Russian River.

Frequently asked questions about holiday rentals in Healdsburg, CA

  • What are some interesting places to visit in or near Healdsburg, CA?

    Healdsburg is a charming town, and you'll find plenty to see. The Healdsburg Museum is well worth a visit, showcasing local history and art. If you're a wine enthusiast, the Russian River Valley is just a short drive away, with many wineries offering tours and tastings. For a day trip, drive out to the Armstrong Redwoods State Natural Reserve - it's a beautiful spot with towering redwood trees.
  • What are the best Airbnb and holiday rentals in Healdsburg, CA?

  • Which walking or cycling routes are the best in Healdsburg, CA?

    There are some lovely walks and cycle routes around Healdsburg. The Healdsburg Plaza is a great place to start a walk, and you can head towards the Healdsburg Museum. The Healdsburg Avenue bike path is a popular choice, and it runs along the Russian River. For a more challenging ride, try the Healdsburg to Windsor Wine Trail, which offers stunning views of the vineyards.
  • What are the most popular Airbnbs in Healdsburg, CA?

    Among the Airbnbs in Healdsburg, CA, Healdsburg Garden House, The Loft Under The Oaks and The Roost - Sun Room are the most popular ones.

  • What sports or outdoor activites can visitors enjoy in and around Healdsburg, CA?

    Healdsburg is a great place for outdoor activities. You can go hiking in the nearby mountains, or try kayaking or paddleboarding on the Russian River. There are several golf courses in the area, and you can even go horseback riding. For a more relaxed day, visit the Healdsburg Farmers Market, held every Sunday.
  • What are the best holiday rentals with a pool in Healdsburg, CA?

  • What other towns or cities can be easily accessed from Healdsburg, CA?

    From Healdsburg, you can easily reach other towns and cities in Sonoma County. Santa Rosa, the county seat, is about a 20-minute drive. You can also visit the charming town of Windsor, known for its wineries, or head to the coast and explore the beautiful beaches of Bodega Bay.
  • What are the best rentals for families and kids in Healdsburg, CA?

  • What amenities are commonly available in vacation rentals in Healdsburg, CA?

    Vacation rentals in Healdsburg typically offer a range of amenities, depending on the property. Many rentals include kitchens, laundry facilities, and outdoor spaces like patios or balconies. Some also have private pools or hot tubs, and some are pet-friendly. You can find rentals in various sizes, from cosy cottages to spacious houses.
  • What are the best rentals or Airbnbs with a jacuzzi in Healdsburg, CA?

  • What time of year is best to rent a vacation rental Healdsburg, CA?

    Healdsburg is beautiful year-round, but the best time to visit depends on your preferences. Spring and autumn are ideal for mild weather and vibrant colours, while summer is perfect for outdoor activities and warm temperatures. If you prefer fewer crowds, consider visiting in the shoulder seasons, April-May or September-October.
  • What are the local dishes in Healdsburg, CA region?

    Healdsburg is known for its fantastic food scene. You'll find many restaurants serving fresh, local produce. Try the Sonoma County Lamb with rosemary and garlic, or the fresh seafood dishes. The region is also known for its artisanal cheeses and wines, so be sure to sample some of those.

Popular destinations

Popular Holiday Rentals with a Terrace in Healdsburg, CA, United States

Catch the morning breeze and watch the local world go by from holiday rentals featuring an outdoor balcony in Healdsburg, CA, United States.

Luxury 1-br Cottage On 30-acre Vineyard Property In Enchanting Healdsburg - Healdsburg, CA
10 3 reviews

Luxury 1-br Cottage On 30-acre Vineyard Property In Enchanting Healdsburg

cottage, Healdsburg
This charming cottage is located in Geyserville, just a short 5km drive from Healdsburg and within walking distance of Unti Vineyards, making it a perfect base for exploring the region's wineries. The cottage offers a relaxing escape for couples, with a comfortable bedroom and bathroom.
The cottage comes equipped with a modern kitchen, a cosy fireplace, and a private outdoor space, perfect for enjoying the California sunshine. Guests can also enjoy the convenience of on-site parking and access to Wi-Fi and satellite TV.
Luxury 2-br Cottage On 30-acre Vineyard Property In Enchanting Healdsburg - Healdsburg, CA
No reviews

Luxury 2-br Cottage On 30-acre Vineyard Property In Enchanting Healdsburg

cottage, Healdsburg
This Dry Creek Valley cottage, situated in Geyserville approximately 16km from Healdsburg and its attractions including the Healdsburg Museum and Raven Performing Arts Theatre, offers a luxurious vineyard escape.
This 1000 sq ft self-catering property boasts two bedrooms, two bathrooms, sleeps four guests, and includes Viking appliances, Restoration Hardware furniture, and a private porch overlooking a 30-acre vineyard; nearby wineries such as Unti Vineyards and Truett Hurst are easily accessible.
Starlite Atelier: Alexander Valley Winery, Hot Tub - Healdsburg, CA
No reviews

Starlite Atelier: Alexander Valley Winery, Hot Tub

apartment, Healdsburg
This Geyserville property offers a prime location for exploring the local wine region, situated a short walk from Starlite Vineyards and a 4-minute drive from Silver Oak Alexander Valley.
This 186 square metre holiday home accommodates up to six guests with three bedrooms and two bathrooms, featuring a private garden, terrace, air conditioning, a hot tub, and a fully equipped kitchen.
Lytton Station Vineyard - Stunning 360-degree Vineyard Views - Healdsburg, CA
9.8 38 reviews

Lytton Station Vineyard - Stunning 360-degree Vineyard Views

apartment, Healdsburg
This luxurious four-bedroom villa is located on a hill in Healdsburg, offering stunning views of the Alexander Valley and surrounding vineyards, just a short distance from Jordan Vineyard & Winery and Ridge Vineyards - Lytton Springs. It has received excellent user ratings, making it a popular choice for travellers.
The property features a spacious living area with a gourmet kitchen, a separate games room, and a luxurious master suite with a double-sink bathroom. Outside, guests can enjoy a private pool and spa, a half basketball court, a bocce ball court, and a bubbling pond with a waterfall.

Popular Dog-Friendly Holiday Rentals in Healdsburg, CA, United States

Give your four-legged companion a cozy place to curl up at pet-friendly holiday rentals in Healdsburg, CA, United States.

Three-building Healdsburg Homestead With Wine Barn - Healdsburg, CA
9.7 156 reviews

Three-building Healdsburg Homestead With Wine Barn

apartment, Windsor
This Healdsburg homestead, situated on the Eastside, offers a unique three-building layout comprising a renovated main house, a studio cottage, and a barn with a wine-tasting bar and games room, all located directly opposite Rodney Strong and J Vineyards.
The property boasts ample outdoor space including a 0.048 hectare fenced lawn, a bocce court, and sleeps eight guests across four bedrooms and one bathroom, featuring a well-equipped kitchen with two dishwashers and air conditioning in the main house and studio.
Guesthouse On Gated 22 Acre Family Ranch, Vineyard - Healdsburg, CA
10 55 reviews

Guesthouse On Gated 22 Acre Family Ranch, Vineyard

house, Windsor
This Casita is located in the foothills between Healdsburg and Windsor, just a short drive from the historic Healdsburg Plaza. The property enjoys excellent user, location and cleanliness ratings.
The Casita offers 830 square metres of living space plus a 320 square metre patio, accommodating up to four guests. It features a private covered terrace, a fully equipped kitchen, air conditioning, a garden, parking, and internet access.
Wine Country Home Of Healdsburg Wine Maker - Healdsburg, CA
9.5 184 reviews

Wine Country Home Of Healdsburg Wine Maker

apartment, Windsor
This six-bedroom Windsor house, a short walk from Old Vineyard Park and 8km from Healdsburg, offers easy access to local amenities including Starbucks and Russian River Brewing Company.
The 241-square-metre property boasts a spacious open-plan layout, sleeping up to ten guests, and includes a fully equipped kitchen, jacuzzi, private garden with hot tub, and complimentary wine from the owner's Christopher Creek Winery with discounted access and pool access for wine club members.
Villa Terra Bella, By Vinifera Homes - Healdsburg, CA
9.8 8 reviews

Villa Terra Bella, By Vinifera Homes

house, Windsor
Villa Terra Bella, a six-bedroom property in Windsor, California, boasts a seven-acre vineyard setting, situated 2.6 km from KIN Windsor and 2.7 km from Windsor Town Green.
This luxurious holiday home sleeps twelve guests and offers a chef's kitchen, private pool, basketball court, BBQ, shuffleboard, and proximity to several renowned wineries.
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