Vacation rentals in Healdsburg, CA

This private 1.5-acre apartment, surrounded by vineyards and oak trees, offers tranquility and seclusion just minutes from Healdsburg Square and Montage Resort. With excellent user, location, and cleanliness ratings, this apartment is a top choice for travelers seeking a comfortable and convenient stay in Healdsburg.
The apartment features an open concept living area with a spacious kitchen, two family rooms, and three bedrooms and bathrooms, accommodating up to eight guests. Amenities include air conditioning, a sparkling hot tub, a garden, parking, and pet-friendly accommodations for an additional fee. Guests can also enjoy direct access to Chiquita Road, renowned for world-class cycling, and panoramic views of the surrounding vineyards.

This historic winery estate home is located in Geyserville's vineyard region, offering vineyard views and immediate proximity to Trentadue Winery, with Healdsburg Plaza just a 5-mile drive away.
This family-friendly apartment features 3 bedrooms, 3 bathrooms, and accommodates up to 6 guests with amenities including air conditioning, a private swimming pool, a garden, on-site parking, and complimentary wine tastings at four local wineries.

This 3-bedroom, 3-bathroom vacation rental home is located less than 8 minutes from downtown Healdsburg, in the rolling hills of Dry Creek Valley. With excellent user, location, and cleanliness ratings, this apartment is an excellent option for travelers visiting Healdsburg.
The apartment has an open floor plan with a spacious living area, a dining room, and a well-equipped kitchen. The apartment can accommodate up to 6 guests and features modern amenities such as a Sonos sound system, Xfinity Wi-Fi, and Lutron smart lighting controls. Guests can also enjoy the outdoor amenities, which include a large heated swimming pool, a hot tub, a covered arbor living/dining and cooking area, and a gas fire pit.

This Healdsburg vacation home offers a peaceful retreat in the heart of Sonoma County wine country, just minutes from the renowned Luther Burbank Center for the Arts. The house has received excellent ratings for its location, cleanliness, and user experience.
The house has three air-conditioned bedrooms and two bathrooms, and can accommodate up to seven guests. The 1,700-square-foot house has a fully equipped kitchen, a private pool, a Jacuzzi, a garden, a tennis court, and parking. Children will enjoy the on-site playground, while adults can explore the scenic Healdsburg countryside on the nearby cycling trails.

This family-friendly vacation home is located on the waterfront in Healdsburg, within a mile of the Russian River, Pezzi King Winery, and within two miles of the Healdsburg Museum and Healdsburg Plaza. The home has earned excellent ratings for its location, cleanliness, and overall experience.
This spacious five-bedroom home, with a sofa bed, accommodates up to 12 guests and offers a private pool, spa tub, fitness center, and tennis court. The home also includes a fully equipped kitchen, barbecue grills, and a terrace for enjoying the beautiful Healdsburg scenery.

This 2-bedroom, 2-bathroom cottage is situated on a one-acre property just outside Healdsburg, offering a private retreat 5 minutes from Downtown Healdsburg Plaza and a 7-minute drive to Memorial Beach on the Russian River.
This newly remodeled 960-square-foot rental accommodates up to 4 guests with a fully equipped kitchen, air conditioning, private patio with BBQ, and parking for three vehicles, providing an ideal base for exploring nearby Dry Creek Valley wineries.

This Healdsburg vacation home boasts an oceanfront location near renowned wineries like Medlock Ames, Silver Oak Alexander Valley, and Starlite Vineyards, all within a 1-2 mile radius.
This 2,500-square-foot house features three bedrooms, two bathrooms, accommodates six guests, and includes a private pool, hot tub, and fully equipped kitchen.

Cottages At Healdsburg is centrally located in Healdsburg, within walking distance of shops, restaurants, and wineries. The resort offers private cottages with one bathroom and a guest capacity of two.
Cottages At Healdsburg has an outdoor pool, a conference hall, and free parking. The resort also offers a concierge service and enhanced cleaning measures.

This Healdsburg house is located just a short walk from the Russian River, offering easy access to scenic beauty, water activities, and nearby wineries. The house is also conveniently close to the Healdsburg Golf Club and Healdsburg District Hospital, making it a great base for exploring the area. The house has received excellent ratings for user experience, location, and cleanliness.
This 2-bedroom, 2-bathroom house spans 1520 square feet. It comes with a fully equipped kitchen, a private fenced yard, a fireplace, free WiFi, and housekeeping services upon request.

This family-friendly vacation home in Healdsburg is located by the sea, within 2 miles of the Russian River and Healdsburg Golf Club. It has an excellent user rating and can accommodate up to 8 guests in its 2000 square feet, 3 bedrooms, and 2 bathrooms.
The house features a kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, a Jacuzzi, a terrace/balcony, a garden, a spa, a concierge, and parking. It also has stunning ocean views and offers concierge services, limo/town car service, and a spa tub for a luxurious stay.

This four-bedroom vacation rental with a one-bedroom guest house is located in the Dry Creek Valley of Healdsburg, just a short drive from the town center.
The 2,200-square-foot home features a private vineyard, a spacious outdoor living area with a pool and hot tub, a gourmet kitchen, and a charming guest house, accommodating up to 10 guests.

This Healdsburg vacation home, situated in a rural area three miles from Pezzi King Winery and within six miles of Dom Whitney Tasting Lounge and Powell's Sweet Shoppe in Windsor, offers peace and quiet while being close to local attractions.
This 2,100-square-foot house features three bedrooms, three bathrooms, and accommodates four guests, boasting a private pool, hot tub, fitness center, and tennis court, along with a fully equipped kitchen and stunning outdoor space.

This luxurious 12-acre estate is located in the Dry Creek/Lytton Springs wine country, just a 5-minute drive from the heart of Healdsburg. This property has received excellent reviews for its amenities and service. The home features a spacious 4,000 square-foot layout with 5 bedrooms and 5 bathrooms, comfortably accommodating up to 12 guests. Guests can enjoy a private pool and hot tub, a full-size bocce court, an outdoor fire pit, a gourmet kitchen, and a private in-law unit.

This Casita is located in the foothills between Healdsburg and Windsor, just minutes from the historic Healdsburg Plaza, offering easy access to wine tasting opportunities. It has excellent ratings for user experience, location, and cleanliness.
The house is a spacious 830 square foot home with a 320 square foot patio, accommodating up to 4 guests. It offers a serene ranch setting with a vineyard, oak groves, winter creeks, and unique rock formations, plus a private covered terrace, a friendly Great Pyrenees dog, and colorful chickens.

This Healdsburg farmhouse, located 8.8 miles from the Luther Burbank Center for the Arts and 5.6 miles from Charles M. Schulz Sonoma County Airport, offers easy access to Healdsburg's attractions and the peaceful countryside.
This 1870-square-foot home features three bedrooms, one bathroom, and accommodates up to 11 guests, boasting a private pool, jacuzzi, tennis court, and fully equipped kitchen with modern appliances.

This family-friendly vacation home is located just three miles from Dry Creek Vineyard, SingleThread Farm, and Unti Vineyards, making it a great base for exploring the Healdsburg wine country. It has received excellent guest ratings, so you can be sure of a comfortable stay.
The house has three bedrooms and four bathrooms, providing plenty of space for up to six guests. Enjoy amenities like a fitness center, spa tub, and outdoor barbecue grills, perfect for relaxing after a day of wine tasting or hiking.