Vacation Rentals in Healdsburg, CA

This Windsor holiday home is situated 4km from Windsor Golf Club and within a 10-minute walk of Dom Whitney Tasting Lounge and Powell's Sweet Shoppe.
This five-bedroom property boasts 241 square metres of space, sleeps eight guests, and includes a jacuzzi, private garden, and free Wi-Fi; barbecue facilities are available for al fresco dining.

This detached Barrel House in Healdsburg's Dry Creek Valley is set on approximately 0.8 hectares, offering seclusion and proximity to Mazzocco Winery, Wilson Winery, and SingleThread Farm at Dry Creek.
This spacious 260-square-metre dwelling accommodates up to eight guests across three bedrooms and four bathrooms, featuring a chef's kitchen, a stone fireplace, a swimming pool, a jacuzzi, a separate gym, and two internet networks, alongside a Tesla charger and a whole-house generator.

This spacious house is located just on the edge of Healdsburg in the Dry Creek Valley, placing it within easy reach of the town's attractions and the surrounding wine country. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The house comfortably accommodates up to eight guests with three bedrooms and two bathrooms. Guests can enjoy a range of amenities, including a heated pool, a hot tub, a fully equipped kitchen, a gym, a games room, and a barbecue area, offering plenty of opportunities for relaxation and entertainment.

This Foothills of Windsor house, minutes from local wineries and a 48km drive from Calistoga, offers direct access to a regional park with lakes and hiking trails.
The self-contained property sleeps four in two bedrooms and two bathrooms, boasting a well-equipped kitchen, private garden with barbecue, swimming pool, jacuzzi, and parking; nearby amenities include tennis courts and a playground.

This charming cottage is located in Healdsburg, just one and a half kilometres from the Healdsburg Plaza and the Russian River, in a peaceful residential area. Guests have consistently rated the cottage highly for its cleanliness, location, and overall experience.
The two-bedroom cottage spans 93 square metres and comfortably accommodates up to four guests. It boasts a modern kitchen, a relaxing spa tub, a private garden, and a barbecue grill, perfect for enjoying the beautiful Healdsburg weather.

This charming cottage is situated on Dry Creek Road in Healdsburg, just 1.6km from the town centre and its wineries, restaurants, and tasting rooms. It has received excellent ratings for its location, cleanliness, and overall experience.
The property offers a spacious layout with two bedrooms and two bathrooms, accommodating up to four guests. Enjoy panoramic vineyard views from the wrap-around deck, relax in the private hot tub, and make use of the fully equipped kitchen, Tesla charging station, and pet-friendly fenced yard.

This luxurious 4-bedroom villa is located just 5 kilometres from the centre of Healdsburg, in the heart of the Dry Creek/Lytton Springs wine country, offering stunning views of the surrounding vineyards and Mount Saint Helena. It has received excellent guest reviews and is perfect for a large group looking for a relaxing and memorable getaway.
This spacious 372 square metre property can accommodate up to 12 guests and features a fully equipped kitchen, a private pool and hot tub, a Bocce court, a fire pit, and a separate in-law suite. The villa also boasts a Sonos sound system, high-speed WiFi, a new HD Smart TV with premium channels, and a Baby Grand Steinway piano, making it the perfect place to unwind and enjoy all that Healdsburg has to offer.

This detached property in Healdsburg is set on 4,048 square meters of private land, located 800 metres from Healdsburg Plaza, a hub for shops and restaurants.
This accommodation sleeps up to seven guests across two bedrooms and two bathrooms, offering 89 square meters of living space with a fully equipped kitchen, air conditioning, a garden, Wi-Fi, and on-site casino entertainment, plus proximity to cycling routes.

This luxurious Healdsburg residence is situated a short 8-km drive from the Russian River and 5.6 km from Healdsburg Plaza, offering convenient access to local attractions.
This six-bedroom, eight-bathroom property sleeps twelve guests and boasts a heated pool, Jacuzzi, tennis court, and fully equipped kitchen, alongside in-house amenities such as table tennis and Wi-Fi, perfect for large family gatherings or group getaways.

This modern luxury apartment is located just 5.6km from Windsor and 5.6km from Healdsburg, offering easy access to both towns' attractions and amenities. It has received excellent guest ratings, making it a popular choice for travellers seeking a comfortable and stylish stay.
The apartment is spacious and can accommodate up to eight guests. It features a fully equipped kitchen, a private garden with a heated pool and hot tub, and a range of smart home features, including a wall-mounted smart TV and a convenient work station.

Casa Campo is a secluded two-bedroom, two-bathroom cottage situated on a one-acre property just 5 minutes from Healdsburg's Downtown Plaza and the wineries of Dry Creek Valley.
This 89-square-metre cottage comfortably accommodates four guests with a fully equipped kitchen, private patio with a gas BBQ, and in-unit laundry, all within easy reach of Healdsburg's attractions.

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.

The Cottages at Healdsburg is conveniently located in the centre of Healdsburg, just a short walk from the town square and its shops and restaurants. The charming atmosphere of the surrounding area provides a relaxing and enjoyable experience for visitors.
The cottages offer comfortable accommodation for up to two guests. Guests can enjoy a range of amenities, including a swimming pool, a restaurant, and a terrace or balcony.

This family-friendly holiday home is situated just 10km from attractions like Matrix Winery, Russian River, and Healdsburg Golf Club, offering a peaceful escape in the mountains. The property consistently receives excellent ratings for user experience, location, and cleanliness.
The 353 square metre property has four bedrooms and four bathrooms, providing ample space for a comfortable stay. Guests can enjoy a range of amenities, including a private pool, a spa, a tennis court, and a fully equipped kitchen, ensuring a luxurious and enjoyable experience.

This family-friendly holiday home is located in a peaceful rural setting, just 3 kilometres from Pezzi King Winery and the Russian River. It has received excellent guest reviews and offers a tranquil escape from the hustle and bustle of town.
The property has 4 bedrooms and 5 bathrooms, covering a spacious 397 square metres, and can comfortably accommodate up to 10 guests. Enjoy a private pool and spa tub, a fully equipped kitchen, a fitness centre, a garden and barbecue grills for outdoor dining.

This modern ranch house is located on Alexander Valley Road, just 4 km north of Healdsburg's town centre and the Healdsburg Plaza, surrounded by vineyards. The property has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The spacious single-storey property offers 186 square metres of living space, comfortably accommodating up to 8 guests. Enjoy a range of amenities including a private pool, a hot tub, a fully equipped kitchen, a large entertainment area, and a garden, perfect for relaxing and enjoying the beautiful surroundings.