Vacation rentals in Healdsburg, CA

About: This waterfront house in Healdsburg is perfect for travelers seeking a tranquil getaway. It's just 2 miles from Russian River, Pezzi King Winery, Healdsburg Museum, and Healdsburg Plaza. With excellent user, location, and cleanliness ratings, this house is highly recommended.

The 6000-square-foot house has five bedrooms, a sofa bed, and can accommodate up to 12 guests. It offers a private pool, a spa tub, a fitness center, a barbecue grill, and a tennis court. The house also features a fully equipped kitchen, free WiFi, and a fireplace, ensuring a comfortable and relaxing stay.

About: The Barrel House is an excellent-rated vacation rental located in the peaceful and scenic Dry Creek Valley, a short drive away from the town of Healdsburg.

With three bedrooms, four bathrooms, and a floor area of 2,800 square feet, this house can accommodate up to eight guests. It features an array of amenities, including a private pool, hot tub, garden, and a private gym. Guests also have access to a concierge, parking, and a Tesla charger.

About: This studio is located in the heart of Healdsburg, within easy walking distance of the town's vibrant downtown area and its attractions. It has excellent user, location, and cleanliness ratings.

The studio has a private gated entry leading to a secluded cottage, with a fully equipped Pilates studio, a landscaped garden with al fresco dining and lounge area, and contemporary art adorning the walls. It has one bedroom, one bathroom, and can accommodate up to two guests. Amenities include air conditioning, a kitchen with fridge and microwave oven, a skylighted shower room with heated stone floor, parking, a fitness center, and personalized excursion planning.

About: Cottages At Healdsburg is a resort in Healdsburg, CA, featuring unique accommodations with private pools and fireplaces. The resort is within walking distance of Raven Performing Arts Theater (1 mi/2 km) and Russian River, and a short drive from Healdsburg Center for the Arts and Healdsburg Plaza (5 minutes).

This highly-rated resort offers a comfortable and connected stay with free WiFi, Smart TVs with digital channels, and furnished balconies or patios. Amenities include an outdoor pool, concierge services, a smoke-free environment, a garden, and free self-parking. Guests can enjoy a luxurious and private retreat with a maximum capacity of 2 guests per cottage.

About: This Healdsburg studio is surrounded by vineyards, yet within walking distance of downtown's attractions. It has excellent user, location, and cleanliness ratings.

The studio has one bedroom, one bathroom, and can accommodate two guests. It features a kitchen, air conditioning, a garden, parking, and Wi-Fi. Guests can also enjoy the private garden with seasonal produce, two patios, and complimentary bikes.

About: This centrally located accommodation in Healdsburg is surrounded by vineyards, a short walk from the town square and Russian River Beach. It has excellent user, location, and cleanliness ratings.

The accommodation has 2 bedrooms, 2 bathrooms, and can accommodate up to 6 guests. It features a spacious and comfortable layout with a large covered redwood deck with a gas grill, a fully equipped kitchen, and modern amenities such as 1 GB high-speed Ethernet, 50" HDTVs with streaming services, and air conditioning/heating in each room. Guests can also enjoy a vineyard and riverfront setting with organic gardens and proximity to Memorial Beach and the Russian River.

About: Immerse yourself in the heart of Sonoma wine country at this charming accommodation, situated on the corner of Chardonnay and Pinot Noir in Windsor. Just steps from the town green, this two-room suite offers easy access to dining, shopping, and entertainment options.

Highly rated for its excellent location, cleanliness, and user experience, this accommodation features a private entrance and patio, a well-equipped kitchenette, and ample closet space. Guests can enjoy hot air balloon viewing from the patio, explore nearby hiking and walking trails, and relax in front of the new 40" flat-screen TV. With a guest capacity of four, this accommodation is perfect for couples, small families, or friends seeking a comfortable and convenient stay in Windsor.

About: 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.

About: This 3-bedroom, 4-bathroom apartment is only a few miles from Healdsburg's town square, giving easy access to the city's attractions. With excellent user, location, and cleanliness ratings, this modern open design apartment offers abundant natural light and a fully equipped kitchen.

Accommodating up to 6 guests, the apartment features expansive decks and open spaces for indoor-outdoor living. Guests can enjoy access to outdoor activities such as boating, fishing, hiking, and kayaking, as well as amenities like air conditioning, a garden, parking, and exterior security cameras for added peace of mind.

About: Located in the exclusive gated community of Windsor, the "Castle" is just minutes from downtown Windsor, renowned wineries, and major cities like San Francisco. With excellent user, location, and cleanliness ratings, this 3,000+ sq ft luxury home offers 6 bedrooms, 3 full bathrooms, and a guest capacity of 8.

The "Castle" features a full wet bar, ping pong table, and foosball table for entertainment, and a sprawling backyard with an oversized patio deck, BBQ grill, "WINE BARn," fire pit, hot tub, and multiple gathering areas.

About: 1083 Guest House is a private, gated cottage located in a wooded area in Healdsburg, within walking distance of the city's renowned restaurants, wineries, and boutiques. It has an excellent user rating, location rating, and cleanliness rating.

The cottage has one bedroom, one bathroom, and a guest capacity of two. It features a fridge, microwave oven, dishwasher, air conditioning, jacuzzi, garden, and parking. Guests can enjoy a private hot tub, continental breakfast, garage and garden area access, and potential sightings of wildlife.

About: This family-friendly house is in a rural setting in Healdsburg, within a 3-mile radius of Simi Winery, Jordan Vineyard & Winery, Russian River, and Ridge Vineyards - Lytton Springs. It has excellent user, location, and cleanliness ratings.

The house has 3 bedrooms and a sofa bed in the living room, a floor area of 2000 square feet, and can accommodate up to 8 guests. It features a well-equipped kitchen, a spa tub, an arcade, barbecue grills, a patio, and a garden.

About: This family-friendly home is located one mile from downtown Healdsburg, within walking distance, and offers all the amenities you need for a comfortable stay. It has received excellent ratings for its location, cleanliness, and user experience.

The home has four bedrooms, three bathrooms, and can accommodate up to nine guests. It features a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a garden, a fitness center, and parking. It also has a solar-heated pool, a hot tub, a children's playground, a trampoline, a bocce ball court, a small basketball court, and a viewing/chilling out deck.

About: Located in the acclaimed wine region of Healdsburg, California, Xanadu Healdsburg vacation home offers an unforgettable experience with its exceptional location and amenities. Guests have highly rated the property for its cleanliness, location, and overall user experience.

The spacious home boasts 3,890 square feet of living space, featuring four bedrooms and a guest capacity of eight. It offers a fully equipped kitchen, a private pool, a terrace with stunning mountain views, a children's playground, and access to cycling trails. Guests can also enjoy amenities such as air conditioning, a spa, a tennis court, and free Wi-Fi.

About: Just 1.4 miles from Healdsburg's town square on Dry Creek Road, this apartment is uniquely located on a private property with tranquil vineyard views. With excellent user, location, and cleanliness ratings, this apartment is highly recommended. The main house has 3 bedrooms and 3 bathrooms, accommodating up to 6 guests, while the separate pool house offers additional space and indoor-outdoor living.

Enjoy a private pool, lanai, and tasting bar, as well as a game barn and pasture for activities. The fully equipped kitchen, Tesla charger, and solar battery wall provide modern conveniences. The master suite boasts vineyard views, and the apartment is pet-friendly and family-friendly, with internet access and air conditioning.

About: This Healdsburg apartment offers a tranquil wine country home experience surrounded by vineyards. It is close to Healdsburg Plaza, the Russian River, and Sonoma County wineries. It has received excellent ratings for its location, cleanliness, and user experience.

Inside, the apartment features a modern farmhouse feel with open-beamed high ceilings, polished concrete floors, and natural fiber area rugs. It has 3 bedrooms, a guest capacity of 6, a gourmet kitchen, and an entertainment room. Guests can enjoy swimming in the heated saltwater pool, playing bocce ball, grilling, or relaxing on the covered porch.

About: This Healdsburg cottage is located within a 2-mile radius of Krug Event Center, Seghesio Family Vineyards, Simi Winery, and Raven Performing Arts Theater. The cottage has excellent user ratings.

The cottage has one bedroom, one bathroom, and a guest capacity of two. The cottage has a private pool, cozy fireplace, fully equipped kitchen, TV with DVD player, patio, barbecue grills, spa tub, and air conditioning.

About: This modern ranch house is situated in the desirable Alexander Valley neighborhood of Healdsburg, just minutes from downtown. It has excellent user, location, and cleanliness ratings.

The apartment has a floor area of 2000 square feet and can accommodate up to 8 guests in 3 bedrooms. It features a secluded vineyard setting on an acre of land, a spacious outdoor entertainment area with a pool, spa, bocce and basketball courts, a professionally decorated and furnished interior with hardwood floors and a gourmet kitchen, and a master suite with a free-standing shower and double mirror doored closets.

About: This family-friendly house in Healdsburg boasts 2000 square feet of space, a swimming pool, and a Jacuzzi, making it the perfect choice for a relaxing getaway.

The house features a fully equipped kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning and internet access for your convenience. It also has 1 bathroom and ample parking space.

About: This family-friendly vacation home in Healdsburg is located in a tranquil rural setting within 3 miles of Pezzi King Winery and Russian River. With excellent user ratings, this house offers a perfect blend of comfort and convenience for travelers seeking a memorable stay in Healdsburg.

Spanning 4270 square feet, this 4-bedroom, 5-bathroom house accommodates up to 10 guests. It features a fully equipped kitchen, a private pool, a fitness center, a spa tub, a garden, and barbecue grills. Guests can enjoy the convenience of on-request housekeeping services, ensuring a hassle-free vacation.

About: River View Lodge is a secluded haven perched on a hillside overlooking the Russian River, just 14 miles from Healdsburg's vibrant downtown. With excellent location and cleanliness ratings, this 3-bedroom, 1600-square-foot house comfortably accommodates up to 8 guests.

The lodge features a fully equipped kitchen, two luxurious bathrooms, a spacious patio and balcony, a relaxing hot tub, and a tennis court. Guests can enjoy outdoor activities such as cycling, exploring the nearby Safari West wildlife preserve, and visiting the awe-inspiring Petrified Forest.

About: Located on a quiet lane within walking distance of downtown Healdsburg, this studio offers a unique and peaceful getaway in the heart of wine country. With excellent user, location, and cleanliness ratings, this spacious studio is ideal for families or groups of up to 12 guests.

The 2170 square foot studio features three bedrooms, three bathrooms, a fully equipped kitchen, air conditioning, a Jacuzzi, a terrace, a garden, and parking. Guests can also enjoy access to the artist's former studio and gallery, as well as a private outdoor shower.

About: Perched on S. Fitch Mountain with panoramic river views, this charming 1927 cottage is just 6 minutes from Healdsburg's downtown Plaza. With excellent user, location, and cleanliness ratings, this two-bedroom, two-bathroom cottage accommodates up to six guests.

Featuring original Douglas Fir flooring, vaulted open-beamed ceilings, and a wraparound veranda, this cottage combines historic charm with modern amenities such as a fully equipped kitchen, Smart TVs, and a Bluetooth sound system. Guests can relax in the private 6' circular hot tub spa, enjoy seasonal river access via wooden stairs, and unwind on the wraparound porch or riverfront beach.

About: This sunny riverfront home in Healdsburg offers direct Russian River access and is less than 10 minutes from Healdsburg's Town Square. It has received excellent ratings for its location, cleanliness, and user experience.

The apartment has a floor area of 1000 square feet and can accommodate up to 4 guests. It features two living spaces, three bedrooms, two bathrooms, a well-equipped kitchen, and multiple outdoor relaxation areas, including a screened porch and a lounge area. It also provides amenities such as Wi-Fi, cable TV, a wood stove, a spa, parking, and direct access to the Russian River with a private patio for river views.

About: This traditional ranch-style home is situated in a tranquil residential area just 5 minutes from the vibrant heart of Healdsburg. It received excellent ratings for its location, cleanliness, and user experience. The home offers a modern farmhouse interior with 3 bedrooms, 2 bathrooms, and a guest capacity of 8.

Amenities include a fully equipped kitchen, comfortable furnishings, air conditioning, a garden, parking, and access to Wi-Fi. The property also boasts nearly 3/4 of an acre of outdoor space, including a bocce court, deck, and patio, perfect for relaxation and entertainment.

About: This apartment is located in a tranquil wine country setting, a 5-minute drive from downtown Healdsburg. It has excellent user, location, and cleanliness ratings.

The apartment has 3 bedrooms, 2 bathrooms, and a guest capacity of 6. It features a private yard with an outdoor dining area, BBQ, and fire pit, as well as a 600+ square foot game room with a pool table, Foosball, and more. Other amenities include a hot tub, air conditioning, a well-equipped kitchen, and top-of-the-line bedding.

About: This 4-bedroom, 3-bathroom vacation rental home in South Windsor provides a quiet retreat just a short drive from the Detroit Riverfront and the Ambassador Bridge. Guests rave about its excellent location, cleanliness, and user rating.

With a spacious layout for up to 10 guests, the home features two separate living rooms, a well-equipped kitchen, an outdoor grilling area, an elegant dining room, and a charming decor. It also includes amenities such as air conditioning, internet, a garden, and parking, making it an ideal choice for families and groups visiting Windsor.

About: This secluded cottage on Dry Creek in Healdsburg is a 15-minute walk from the bustling Healdsburg Plaza, offering shops, restaurants, and attractions. With excellent user, location, and cleanliness ratings, this cottage is a top choice for travelers visiting Healdsburg.

The cottage has two king bedrooms with in-suite bathrooms, a king Murphy bed and full bath in the living space, and a full kitchen. It also features a spacious deck, air conditioning, a Jacuzzi, a garden, parking, and EV charging outlet. Guests may encounter foxes and other wildlife on the property.

About: This 2-bedroom vacation home in Healdsburg offers a relaxing getaway with its private spa tub and smoke-free environment. It is conveniently located within 1 mile of Krug Event Center and Wilson Winery.

With a spacious layout, the house features a fully equipped kitchen, a DVD player, and a sofa bed for additional sleeping capacity. Guests can enjoy outdoor barbecues on the terrace or balcony, or relax in the garden.

About: This 2-bedroom, 2-bathroom vacation home in Healdsburg is highly rated by previous guests and offers a unique combination of comfort and convenience. Located within walking distance of the Russian River and just 3 miles from Healdsburg's main attractions, this vacation home provides easy access to wineries, golf courses, and museums.

With 1380 square feet of living space, this vacation home can accommodate up to four guests and features a fully equipped kitchen, a private balcony, access to barbecue grills, and free Wi-Fi. The house is also pet-friendly and offers optional housekeeping services, ensuring a comfortable and convenient stay for all guests.

About: This charming 2-bedroom, 2-bathroom cabin in Healdsburg's Wine Country district is a perfect getaway for couples or small families. Just a block from the Russian River, it offers easy access to swimming, kayaking, and fishing. The cabin has a cozy interior with a fireplace, two large couches, and a fully equipped kitchen. Outside, there are five decks providing ample space for relaxation, dining, and enjoying stunning views.

With a very good user rating, this cabin accommodates up to 4 guests and features a gas grill, private bathrooms, and parking. It's the perfect place to relax and enjoy all that Healdsburg has to offer.