The Bunkhouse at Side Road Farm is a charming one-bedroom suite situated in Healdsburg, just a short walk from three wineries and nestled on a three-acre site that was once a horse ranch. The property has excellent user, location, and cleanliness ratings. The suite offers a comfortable living space for two guests, and it features a spacious bedroom with a queen-sized bed and a walk-in closet. Guests can enjoy a range of amenities including a Smart TV, a comfortable couch, a kitchen nook with a mini fridge, microwave, and Keurig coffee maker, as well as a private outdoor seating area.
10 14 reviews
Healdsburg, CA
02/10 – 07/10
NZ$1168/nighttotal: NZ$5840 (5 )
Healdsburg Victorian Cottage On Vineyard Estate
2 4
apartment , Healdsburg
This 1895 Victorian cottage in Alexander Valley offers an authentic wine country experience, located 2.1 kilometres from Healdsburg Plaza's tasting rooms and restaurants, and within walking distance of Tongue Dancer Wines (400 metres) and Arnot-Roberts (0.8 kilometres). This two-bedroom, two-bathroom holiday home, spanning 155 square metres and accommodating up to four guests, features two sitting areas with brick fireplaces, a modernised kitchen with marble counters and an induction oven, and two furnished patios with vineyard and mountain views, alongside central air conditioning.
10 77 reviews
Healdsburg, CA
02/10 – 07/10
NZ$783/nighttotal: NZ$3915 (5 )
Healdsburg Wine Country Oasis, Hot Tub & Bocce
2 4
apartment , Healdsburg
This two-bedroom apartment is situated in Alexander Valley, just a few kilometres from the centre of Healdsburg and Geyserville, surrounded by vineyards and offering a peaceful retreat. It consistently receives excellent ratings for its location, cleanliness, and overall guest experience. The property comfortably sleeps up to four guests and features a private backyard with a hot tub, bocce court, and a fire pit. The apartment is equipped with modern amenities, including a fully equipped kitchen, a dedicated workspace, and a private deck.
Healdsburg, CA
20/08 – 23/08
NZ$1273/nighttotal: NZ$3819 (3 )
Serene Riverfront Cottage In Healdsburg Views Kayaks 1 5 Mile To Downtown
1 3
house , Healdsburg
Accommodation. Your accommodation will be based in Healdsburg. Facilities and services include a kitchen, free parking and a barbecue.
9.8 414 reviews
Healdsburg, CA
07/09 – 11/09
NZ$387/nighttotal: NZ$1548 (4 )
Wine Country Cottage In Healdsburg
1 2
apartment , Healdsburg
This studio is located just 1.6 kilometres from downtown Healdsburg, surrounded by vineyards and offering a peaceful setting. It has received excellent ratings for its location, cleanliness and overall experience. The studio provides accommodation for two guests and comes with a fully equipped kitchen, a private garden and a patio. Guests can enjoy fresh produce from the garden, explore the area on two complimentary bikes and even take part in a wine tasting experience with the owner, a second-generation vineyard manager.
9.9 35 reviews
Healdsburg, CA
30/08 – 06/09
NZ$1408/nighttotal: NZ$9856 (7 )
Luxury 1-br Cottage On 30-acre Healdsburg Vineyard
1 2
apartment , Healdsburg
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.
9.5 208 reviews
Healdsburg, CA
07/09 – 11/09
NZ$899/nighttotal: NZ$3596 (4 )
Serene Riverfront Cottage In Healdsburg Views Kayaks 1 5 Mile To Downtown
2 2
house , Healdsburg
Redwood River Lodge is a beachfront property located just 14 miles from the Luther Burbank Center for the Arts in Healdsburg, with Safari West and the Petrified Forest both a short drive away. The lodge has received excellent ratings for its location, cleanliness, and overall user experience. This two-bedroom holiday home spans 111 square metres and comfortably sleeps up to six guests. Amenities include a fully equipped kitchen, a private patio, a Jacuzzi, a tennis court, and free parking, making it ideal for a relaxing and enjoyable stay.
9.9 177 reviews
Healdsburg, CA
19/08 – 24/08
NZ$929/nighttotal: NZ$4645 (5 )
Updated Russian River Cabin (Beach/river Access!)
1 2
cabin , Healdsburg
This charming riverside retreat is located just a short drive from Healdsburg and the Dry Creek Valley wineries, offering a peaceful escape from the hustle and bustle of city life. The property has received excellent ratings for its location, cleanliness and overall experience. The cottage offers a flexible layout with two bedrooms and a spacious living area, comfortably accommodating up to six guests. Guests can enjoy a range of amenities including a fully equipped kitchen, a private outdoor area with a terrace and garden, and a range of water sports equipment such as a canoe, kayak and paddleboards.
9.9 97 reviews
Healdsburg, CA
19/08 – 24/08
NZ$1829/nighttotal: NZ$9145 (5 )
Heron House - Hot Tub And Wine Tastings Included
3 2
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.
10 132 reviews
Healdsburg, CA
07/09 – 11/09
NZ$761/nighttotal: NZ$3044 (4 )
2 Bedroom Flat In Downtown Healdsburg
1 2
apartment , Healdsburg
This upstairs flat is located a short walk from Healdsburg's historic downtown plaza, surrounded by restaurants, bars, and tasting rooms. It has received excellent ratings for location, cleanliness, and overall user experience. The flat has two bedrooms, each with a queen-sized bed, accommodating up to four guests. The kitchen is fully equipped with modern appliances, and the living area features a leather sofa and coffee table, perfect for relaxing or entertaining.
10 74 reviews
Healdsburg, CA
27/06 – 04/07
NZ$1321/nighttotal: NZ$9247 (7 )
Casa De La Esperanza:1890s Gem - Hot Tub - 5bd/3ba
5 2
apartment , Windsor
This Windsor house, a short walk from Windsor's Town Green and the town centre, offers easy access to Windsor Oak Vineyards and is within a 10-15 minute (approx. 8-12 km) drive of the Russian River Brewing Company and Foothill Regional Park. The six-bedroom, four-bathroom property sleeps up to 16 guests, boasting a fully equipped kitchen, high-speed internet (603 Mbps), a Jacuzzi, and multiple covered porches; Roku-equipped TVs and ample parking are also provided.
10 159 reviews
Healdsburg, CA
30/08 – 06/09
NZ$909/nighttotal: NZ$6363 (7 )
Historic Queen Anne Victorian In The Heart Of Windsor
3 2
apartment , Windsor
This holiday home is ideally situated in central Windsor, just a short walk from the Dom Whitney Tasting Lounge and Powell's Sweet Shoppe, and 4.3 km from Windsor Golf Club. The property has received excellent ratings for location, cleanliness and overall experience. The three-bedroom house, with a floor area of 169 square metres, comfortably accommodates up to six guests. The house offers a range of amenities, including a fully equipped kitchen, a private garden with a terrace, a Jacuzzi, a spa, and free Wi-Fi.
Best family friendly Healdsburg, CA holiday rentals
Among the 114 accommodations in Healdsburg, CA, here are the 4 best family friendly rentals
10 39 reviews
Healdsburg, CA
02/10 – 07/10
NZ$2827/nighttotal: NZ$14135 (5 )
Walk To Downtown Healdsburg--luxury Healdsburg Vacation Rental
3 4
apartment , Healdsburg
This family-friendly house is located in Healdsburg, just 2km from the Russian River and Healdsburg Plaza. It has received excellent ratings from previous guests. This spacious house sleeps up to 8 guests and includes a well-equipped kitchen, a private pool, a patio, a fitness centre, and a games room. Guests can enjoy the beautiful garden, the terrace, and the spa, and can also take advantage of the tennis court and the parking facilities.
9.8 121 reviews
Healdsburg, CA
07/09 – 11/09
NZ$738/nighttotal: NZ$2952 (4 )
Morning Dew-a Riverfront Healdsburg Home
3 2
apartment , Healdsburg
This riverfront property is located just under 10 kilometres from Healdsburg town square, offering a peaceful escape from the hustle and bustle, yet remaining within easy reach of all the town’s attractions. The property consistently receives excellent ratings for location, cleanliness, and overall user experience. The three-bedroom apartment, spanning 93 square metres, comfortably accommodates four guests. Guests can enjoy a range of amenities, including a well-equipped kitchen, multiple outdoor spaces, and direct access to the Russian River for swimming, fishing, or simply relaxing on the riverbank.
9.9 98 reviews
Healdsburg, CA
02/10 – 07/10
NZ$1917/nighttotal: NZ$9585 (5 )
Homestead With Pool And Hot Tub - Wine Tastings Included
3 4
house , Healdsburg
Healdsburg Homestead is located in Healdsburg, California, just 15 kilometres from the Charles M. Schulz Sonoma County Airport and a short drive from the Luther Burbank Center for the Arts and Safari West. This property has consistently received excellent ratings for its cleanliness, location, and overall user experience. This three-bedroom, two-bathroom house spans 158 square metres and comfortably accommodates up to seven guests. The property features a private pool, a fully equipped kitchen, a children's playground, free Wi-Fi, and private parking, making it a great choice for families and groups looking for a relaxing and enjoyable stay.
9.9 119 reviews
Healdsburg, CA
30/08 – 06/09
NZ$1749/nighttotal: NZ$12243 (7 )
Views, Hot Tub, Sauna, Cold Plunge, Cinema!
2 2
apartment , Healdsburg
This Healdsburg apartment is situated in a peaceful area, just a short drive from the town square and its many restaurants and shops, offering stunning views of the surrounding vineyards. It has received excellent ratings for user experience, location, and cleanliness. The property is a spacious two-bedroom, two-bathroom dwelling with a guest capacity of four people. Guests have access to a private deck, garden, wine cave, hot tub, gym, and a detached office room, ideal for remote working.
Best Healdsburg, CA holiday rentals with parking
10 101 reviews
Healdsburg, CA
07/09 – 11/09
NZ$743/nighttotal: NZ$2972 (4 )
Luxuriously Appointed Private Large Guest Suite In A Landmark Victorian
1 2
apartment , Healdsburg
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.
10 71 reviews
Healdsburg, CA
02/10 – 07/10
NZ$1577/nighttotal: NZ$7885 (5 )
Completely Remodeled Farmhouse With Stunning Views Of Dry Creek Valley
3 4
house , Healdsburg
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.
9.9 34 reviews
Healdsburg, CA
07/09 – 11/09
NZ$896/nighttotal: NZ$3584 (4 )
Vintage Retreat With Spa Near Healdsburg
3 2
apartment , Healdsburg
This Healdsburg apartment, situated 3.2 kilometres from the town centre and close to Dry Creek Valley vineyards, offers easy access to Healdsburg's attractions. The 150 square metre self-catering property sleeps six, boasting three bedrooms, two bathrooms, a private redwood deck with a six-person hot tub, a well-equipped kitchen with a double oven, and free parking for three cars.
9.8 6 reviews
Healdsburg, CA
07/09 – 11/09
NZ$1120/nighttotal: NZ$4480 (4 )
Vinehaven - 3bd Healdsburg Retreat With Spa
3 2
apartment , Healdsburg
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.
Frequently asked questions about holiday rentals in Healdsburg, CA
What are some interesting places to visit in or near Healdsburg, CA?
Healdsburg is a great base for exploring the Sonoma County area. You can visit the stunning Russian River, with its beautiful redwood forests, or head over to the charming town of Guerneville, known for its quirky shops and riverfront restaurants. If you're a wine lover, you'll be spoilt for choice with the many vineyards and wineries in the area, like the famous J Vineyards & Winery or the historic Chateau St. Jean.
What are the best Airbnb and holiday rentals in Healdsburg, CA?
Which walking or cycling routes are the best in Healdsburg, CA?
The Healdsburg Plaza is a lovely spot for a stroll and people-watching. For a longer walk or cycle, try the Healdsburg to Windsor Trail, a 14-kilometre paved path that runs along the Russian River. It's a great way to enjoy the scenic views and fresh air.
What are the most popular Airbnbs in Healdsburg, CA?
What sports or outdoor activites can visitors enjoy in and around Healdsburg, CA?
Healdsburg is a great spot for outdoor activities. You can go hiking in the nearby Armstrong Redwoods State Natural Reserve, or kayaking on the Russian River. If you're feeling adventurous, you can even go whitewater rafting on the river, especially during the spring months.
What are the best holiday rentals with a pool in Healdsburg, CA?
What other towns or cities can be easily accessed from Healdsburg, CA?
Healdsburg is a great central location for exploring Sonoma County. You can easily drive to Santa Rosa, the county seat, or the coastal town of Bodega Bay. For a day trip, you could even head to San Francisco, which is about a 1.5-hour drive.
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 wide range of amenities, including kitchens, laundry facilities, and outdoor spaces like patios or balconies. Many also have private hot tubs or swimming pools, depending on the size and location of the property.
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 a popular destination year-round, but the best time to visit depends on your preferences. Spring and autumn offer pleasant weather and fewer crowds, while summer is ideal for outdoor activities and wine tasting. If you love the festive atmosphere, you can also visit during the holiday season.
What are the local dishes in Healdsburg, CA region?
The Healdsburg region is known for its delicious farm-to-table cuisine. You can find fresh seafood from the Pacific coast, locally sourced produce, and of course, award-winning wines. Some local favourites include Sonoma County lamb, grilled oysters, and seasonal fruit pies.
Destinations nearby
Best Healdsburg, CA holiday rentals with a balcony
9.8 37 reviews
Healdsburg, CA
07/09 – 11/09
NZ$2608/nighttotal: NZ$10432 (4 )
Lytton Station Vineyard - Stunning 360-degree Vineyard Views
5 2
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.
10 2 reviews
Healdsburg, CA
02/10 – 07/10
NZ$6354/nighttotal: NZ$31770 (5 )
Panorama Estate - Classic Wine Country Villa In Healdsburg
6 4
apartment , Healdsburg
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.
9.6 19 reviews
Healdsburg, CA
02/10 – 07/10
NZ$2309/nighttotal: NZ$11545 (5 )
Healdsburg Homestead With Pool, Hot Tub And Tastings Included
3 4
apartment , Healdsburg
This family-friendly holiday home is located in a rural area of Healdsburg, just 3 kilometres from Krug Event Center, Seghesio Family Vineyards, and Healdsburg District Hospital. The property has received excellent user ratings, making it a popular choice for travellers. This 3-bedroom property spans 158 square metres and can accommodate up to 7 guests. Enjoy a range of amenities including a private pool, a spa, a tennis court, and a fully equipped kitchen.
9.8 224 reviews
Healdsburg, CA
07/09 – 11/09
NZ$911/nighttotal: NZ$3644 (4 )
Stay Surrounded By Fitch Mountain Park And Open Space Preserve.
2 2
house , Healdsburg
This charming villa is located in Healdsburg, just 1 kilometre from the Russian River and within 5 kilometres of Healdsburg Golf Club and Healdsburg District Hospital, offering a peaceful retreat in a quiet neighbourhood. The property has received excellent ratings for its cleanliness, location, and user experience. The 141 square metre villa has 2 bedrooms and 2 bathrooms, offering comfortable accommodation for up to four guests. The villa features a fully equipped kitchen, a private garden with a barbecue, a terrace, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
Best pet friendly Healdsburg, CA holiday rentals
Among the 114 accommodations in Healdsburg, CA, here are the 4 best pet friendly rentals
10 1 review
Healdsburg, CA
07/09 – 11/09
NZ$1816/nighttotal: NZ$7264 (4 )
Farmhouse With Pool, Hot Tub And Tastings Included
3 2
house , Windsor
This Healdsburg farmhouse, situated 14.2 km from the Luther Burbank Center for the Arts and offering easy access to Healdsburg's wineries and cultural attractions, provides a peaceful countryside retreat amongst vineyards. The 174 square metre property sleeps up to 11 guests in three bedrooms, one bathroom, and boasts a swimming pool, jacuzzi, tennis court, and fully equipped kitchen including a dishwasher and microwave; free Wi-Fi and parking are also included.
9.3 16 reviews
Healdsburg, CA
02/10 – 07/10
NZ$668/nighttotal: NZ$3340 (5 )
Windsor Home With Sauna & Outdoor Fire Pit
1 4
apartment , Windsor
This 3-bedroom house is located in Windsor, California, offering a comfortable stay close to local attractions and 3.2 kilometres from Windsor Golf Course. This pet-friendly accommodation for up to 8 guests boasts a private sauna, ice bath, fully equipped kitchen, BBQ grill, fire pit, air conditioning, Wi-Fi, washer/dryer, and free parking.
10 14 reviews
Healdsburg, CA
02/10 – 07/10
NZ$1757/nighttotal: NZ$8785 (5 )
Family-friendly Dry Creek Valley Retreat W/amazing Views <15 Minutes To Square
3 4
apartment , Healdsburg
This family-friendly holiday home is located just 5 kilometres from Dry Creek Vineyard, SingleThread Farm, and Unti Vineyards, making it an ideal choice for wine enthusiasts. It enjoys a peaceful mountain setting, offering breathtaking views and a tranquil escape from the bustling city. The property has received excellent reviews from previous guests, highlighting its comfortable and well-equipped nature. The house spans 223 square metres and comfortably accommodates up to 6 guests in its three bedrooms and four bathrooms. Guests can enjoy a range of amenities, including a fully-equipped kitchen, a spa tub, a fitness centre, a garden, and a terrace, providing everything needed for a relaxing and enjoyable stay.
9.5 114 reviews
Healdsburg, CA
02/10 – 07/10
NZ$2089/nighttotal: NZ$10445 (5 )
Rendezvous Under The Oaks-pool & Hot Spa
3 4
apartment , Healdsburg
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.