Compare Vacation Rentals & Airbnb in Healdsburg, CA

Vineyard Vue, a three-bedroom house in Healdsburg, is conveniently located a 13km drive from Charles M. Schulz Sonoma County Airport and a 19-minute walk from Healdsburg Plaza.
This 158 square metre property offers a fully equipped kitchen, terrace, garden, tennis court, free parking, Wi-Fi, and sleeps up to six guests, with nearby attractions including Safari West and the Luther Burbank Center for the Arts.

This Healdsburg studio apartment, a Mediterranean-style property, is situated in the town centre, just 0.32 kilometres from Healdsburg's restaurants, wine tasting rooms, and shops.
The three-bedroom, three-bathroom apartment sleeps four guests, boasting three private decks with 360-degree views, a gourmet kitchen, a gated entrance, a three-car garage with an EV charger, and access to rooftop and garden patios.

This Windsor self-catering holiday home, situated on a mountainside farm near the Russian River (2.4km) and within 9.6km of attractions such as Dom Whitney Tasting Lounge and Powell's Sweet Shoppe, offers scenic views.
This 174 square metre property sleeps six guests across three bedrooms and four bathrooms, boasting a private garden, swimming pool, hot tub, tennis court, and ample parking, along with a fully equipped kitchen including a dishwasher.

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.

This charming cottage is situated in the Dry Creek Valley, just 10 kilometres from Healdsburg's town centre and a short drive from the Russian River, offering a peaceful retreat amidst beautiful vineyards. The property has received excellent ratings for location, cleanliness, and overall experience.
The cottage is a comfortable and stylish one-bedroom property, perfect for couples seeking a quiet getaway. Guests can enjoy stunning views of the vineyard from the spacious covered porch, relax in the garden, or explore the on-site winery, which produces a variety of award-winning wines.

This Geyserville holiday home offers a peaceful retreat, situated within 2km of Medlock Ames and Starlite Vineyards, and 3km of Silver Oak Alexander Valley.
The one-bedroom, one-bathroom property sleeps two guests and includes a patio, fireplace, Smart TV, DVD player, refrigerator, microwave, coffee maker, free Wi-Fi, and a video library, plus limited housekeeping.

This charming cottage is located just under 3km from the centre of Healdsburg Plaza, nestled in a peaceful rural setting with vineyard views. It has received excellent reviews from previous guests.
The cottage offers 102 square metres of space and can accommodate up to 4 guests. It comes complete with a fully equipped kitchen, a private deck, a jacuzzi, a garden and a spa, making it ideal for a relaxing getaway.

This peaceful house is located just 4 kilometres from Healdsburg Square and 3.8 kilometres from the Montage Resort, nestled in a tranquil setting surrounded by vineyards and oak trees. The property has received excellent user ratings, making it a popular choice for travellers.
The house spans 251 square metres and comfortably accommodates up to 8 guests. The property offers a range of amenities, including a fully equipped kitchen, a hot tub, a terrace, a garden, and a spa, making it an ideal choice for families or groups looking to relax and enjoy the surrounding area.

This family-friendly house is located in Healdsburg, just 3km from the Russian River and Healdsburg Golf Club, offering a peaceful setting close to local attractions. It has received excellent user ratings, making it a popular choice for travellers.
This 186 square metre property offers 3 bedrooms and 2 bathrooms, comfortably accommodating up to 8 guests. Enjoy a range of amenities including a Jacuzzi, spa, terrace, garden, and concierge services, perfect for a relaxing and luxurious stay.

This private house is situated just a few kilometres from the centre of Healdsburg, surrounded by vineyards and offering a peaceful escape from the town's bustle. It has received excellent ratings for location, cleanliness and overall experience.
The house is spacious, covering 232 square metres and accommodating up to six guests across three bedrooms and two bathrooms. Guests can enjoy a fully equipped kitchen, a terrace and garden, and explore the estate's vineyards.

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 Healdsburg apartment, situated 3.2km from the town centre, offers easy access to Dry Creek Valley vineyards and is within easy reach of restaurants, shops, and the Raven Performing Arts Theatre.
The 150 sq m property boasts three bedrooms, two bathrooms, sleeps six, and includes a well-equipped kitchen, a private redwood deck with a hot tub, and parking; two dogs are welcome.

This two-bedroom apartment is situated on a quiet country road just two miles from Healdsburg's bustling centre, offering a peaceful retreat with easy access to the town's attractions. It has consistently received excellent ratings for its cleanliness, location and overall guest experience.
The self-contained apartment comfortably accommodates up to four guests and features a well-equipped kitchen, a private garden, a deck and ample parking. Guests can enjoy the convenience of on-site parking, a fully equipped kitchen, and a private garden, perfect for relaxing after a day of exploring the nearby Dry Creek Valley wineries.

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.

This 3-bedroom Windsor property is located approximately 15 minutes by car from Charles M. Schulz–Sonoma County Airport, a short drive from Windsor Town Green, and offers proximity to the Russian River and Sonoma County's wineries.
This spacious 167 square meter holiday home accommodates up to 8 guests and features a fully equipped kitchen, air conditioning, a private sauna, an ice bath, a BBQ grill, and an outdoor fire pit, with pets permitted for a fee.