Best Holiday rentals and Airbnb offers in Healdsburg, CA
9.8 356 reviews
Healdsburg, CA
02/10 – 07/10
SG$750/nighttotal: SG$3750 (5 )
Peaceful Location, Hot Tub, Fire Pit, Game Room!
1 4
apartment , Healdsburg
This apartment is situated just 5 kilometres from the centre of Healdsburg, in a peaceful location close to the Russian River and Fitch Mountain. The property has received excellent ratings for its location, cleanliness and overall user experience. The apartment is ideal for families or groups of up to six guests, with three bedrooms and two bathrooms. Amenities include a fully equipped kitchen, a games room with a pool table, a hot tub, a garden with a fire pit and outdoor dining area, and parking.
9.0 49 reviews
Healdsburg, CA
20/08 – 23/08
SG$1931/nighttotal: SG$5793 (3 )
Heart Of Healdsburg Cottage For 4, Pool, Spa, Fire Pit, Wifi, Bbq
2 3
cottage , Healdsburg
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.
9.9 43 reviews
Healdsburg, CA
02/10 – 07/10
SG$992/nighttotal: SG$4960 (5 )
Cypress House & Studio, Walk To Healdsburg Plaza
1 4
apartment , Healdsburg
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.
10 45 reviews
Healdsburg, CA
08/07 – 10/07
SG$1137/nighttotal: SG$2274 (2 )
Cuvée House
1 2
apartment , Healdsburg
This charming Queen Anne Victorian property is situated on a quiet street just a short walk from Healdsburg Plaza, offering easy access to the town's restaurants, galleries, and shops. The apartment has received excellent ratings for its location, cleanliness, and overall experience. The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, private parking, and keyless entry, making it a convenient and comfortable base for exploring Healdsburg.
10 4 reviews
Healdsburg, CA
08/07 – 10/07
SG$390/nighttotal: SG$780 (2 )
The Roost - Sun Room
1 2
apartment , Healdsburg
This Healdsburg apartment is conveniently located near the Raven Performing Arts Theatre, Healdsburg Centre for the Arts, and the Healdsburg Museum, all within easy walking distance, and approximately 2.4km from Healdsburg Plaza and Pezzi King Winery. The one-bedroom, one-bathroom flat sleeps two guests and includes air conditioning, Wi-Fi, a terrace, hairdryer, and iron and ironing board; enjoy nearby cultural attractions and wine tasting opportunities.
9.6 234 reviews
Healdsburg, CA
10/07 – 13/07
SG$1160/nighttotal: SG$3480 (3 )
Spectacular Vineyard View!! Spa, Close To Plaza!- 3br/2ba (Up To 8 Guests)
3 2
apartment , Healdsburg
This charming apartment is situated just 1.6 kilometres west of Healdsburg, nestled amongst 30 acres of vineyards, offering a peaceful escape from the bustling town. It has consistently received excellent ratings from previous guests for its location, cleanliness, and overall experience. The apartment comfortably accommodates up to eight guests across three bedrooms and two bathrooms. Enjoy the spacious living area, complete with a decorative fireplace, and relax outdoors on the patio with a barbecue grill, or soak in the Jacuzzi surrounded by the stunning vineyard views.
9.8 50 reviews
Healdsburg, CA
07/09 – 11/09
SG$687/nighttotal: SG$2748 (4 )
Rivers Breeze - Wine Tastings Included
3 2
apartment , Healdsburg
This charming riverside property is located just 5.6 kilometres from Healdsburg Plaza and a short drive from local farms, offering a peaceful escape from the town centre. The apartment has received excellent ratings for its cleanliness, location, and overall experience. The property features three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the well-equipped kitchen, a spacious living area, a garden, a fitness centre, and two kayaks for exploring the river.
9.9 481 reviews
Healdsburg, CA
07/09 – 11/09
SG$284/nighttotal: SG$1136 (4 )
Dry Creek Valley Cottage
1 2
apartment , Healdsburg
This charming cottage is located just a few kilometres from Healdsburg's historic downtown plaza, nestled in the peaceful Dry Creek Valley amidst vineyards and wineries. This accommodation has consistently received excellent ratings for its cleanliness, location, and overall experience. The cottage features one bedroom and one bathroom, comfortably accommodating two guests. Guests can enjoy a private entrance, parking, a garden with fruit trees, and a peaceful setting perfect for relaxing walks and bike rides through the surrounding vineyards.
10 14 reviews
Healdsburg, CA
10/07 – 13/07
SG$987/nighttotal: SG$2961 (3 )
Healdsburg Victorian Cottage On Vineyard Estate
2 2
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.
9.9 97 reviews
Healdsburg, CA
20/08 – 23/08
SG$1330/nighttotal: SG$3990 (3 )
Heron House - Hot Tub And Wine Tastings Included
3 3
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.
10 101 reviews
Healdsburg, CA
19/08 – 24/08
SG$564/nighttotal: SG$2820 (5 )
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.
9.3 270 reviews
Healdsburg, CA
07/09 – 11/09
SG$579/nighttotal: SG$2316 (4 )
Rockhouse Suites
1 2
studio , Healdsburg
This studio apartment is situated just outside of Healdsburg, offering easy access to both the town's attractions and the surrounding countryside, making it ideal for exploring the area. The property enjoys excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay. The studio apartment offers 74 square metres of space, comfortably accommodating two guests. Amenities include a fully equipped kitchenette, a private patio, cable TV, Wi-Fi, plush bathrobes and access to a tranquil garden, providing everything you need for a relaxing getaway.
Best family friendly Healdsburg, CA holiday rentals
Among the 114 accommodations in Healdsburg, CA, here are the 4 best family friendly rentals
9.8 132 reviews
Healdsburg, CA
20/08 – 23/08
SG$836/nighttotal: SG$2508 (3 )
Riverside Cottage: Access And River Views- 1 Miles From Downtown Healdsburg
1 3
apartment , Healdsburg
This charming cottage is situated just a short drive from Healdsburg's downtown Plaza, offering easy access to the town's restaurants, shops, and wineries. The property enjoys excellent ratings for location, cleanliness, and overall user experience. The two-bedroom dwelling comfortably accommodates up to six guests and boasts a well-equipped kitchen, a private hot tub, and a wraparound veranda with stunning views of the Russian River. Guests can enjoy the vintage charm of the cottage, complete with modern amenities, and take advantage of the seasonal river access during the summer months.
9.6 19 reviews
Healdsburg, CA
10/07 – 13/07
SG$2331/nighttotal: SG$6993 (3 )
Healdsburg Homestead With Pool, Hot Tub And Tastings Included
3 2
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.
10 5 reviews
Healdsburg, CA
19/08 – 24/08
SG$648/nighttotal: SG$3240 (5 )
The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !
2 2
apartment , Healdsburg
This Dry Creek Road cottage, situated in Healdsburg's wine country, is approximately 1.6 kilometres from Healdsburg's tasting rooms and restaurants, offering easy access to renowned wineries by foot, bicycle, or car. The stylish, newly built barn conversion sleeps five guests across two bedrooms and two bathrooms, boasting a private hot tub, a fenced yard (pet fee applies), solar power, a Tesla charging station, and panoramic vineyard views.
9.4 3 reviews
Healdsburg, CA
10/07 – 13/07
SG$839/nighttotal: SG$2517 (3 )
Riverbend Retreat - Hot Tub And Tastings Included
2 2
apartment , Healdsburg
This Healdsburg holiday home is located a short drive from Healdsburg Plaza and offers direct access to the Russian River's sandy beachfront across the street. The 158 square metre property boasts two bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, Jacuzzi, private hot tub, and high-speed internet.
Best Healdsburg, CA holiday rentals with parking
10 331 reviews
Healdsburg, CA
07/09 – 11/09
SG$397/nighttotal: SG$1588 (4 )
Rustic Cabin In Dry Creek Valley With Beautiful Views // 5 Miles To Plaza
1 2
cabin , Healdsburg
This Healdsburg cottage enjoys a peaceful rural setting, conveniently located within 9.6km of Dry Creek Vineyard, Healdsburg Plaza, and other local attractions including the Raven Performing Arts Theatre and Healdsburg Museum. The 78 square metre self-catering property sleeps two guests in one bedroom and one bathroom, boasting a fully equipped kitchen, terrace, garden, spa, and free parking.
Healdsburg, CA
10/07 – 13/07
SG$679/nighttotal: SG$2037 (3 )
Private Acre With Bbq Patio 5min To Healdsburg Plaza
1 2
house , Healdsburg
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.
9.5 207 reviews
Healdsburg, CA
20/08 – 23/08
SG$1118/nighttotal: SG$3354 (3 )
River View Lodge - Hot Tub And Tastings Included
3 3
house , Healdsburg
River View Lodge is located in Healdsburg, just 23 kilometres from Safari West and 18 kilometres from Charles M. Schulz Sonoma County Airport. The lodge has received excellent ratings for its cleanliness, location, and overall experience. This three-bedroom lodge spans 149 square metres and comfortably accommodates up to eight guests. The lodge offers a range of amenities, including a fully equipped kitchen, a hot tub, a garden, a tennis court, and free parking.
Healdsburg, CA
20/08 – 23/08
SG$2294/nighttotal: SG$6882 (3 )
Dry Creek Valley Home And Vineyard
3 3
apartment , Healdsburg
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.
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 area. You could visit the stunning redwood forests of Armstrong Redwoods State Natural Reserve, just a short drive away. If you're interested in wine, there are plenty of wineries to visit in the surrounding Sonoma Valley, like the iconic Chateau St. Jean or the family-run vineyards of the Russian River Valley. For art lovers, the Healdsburg Center for the Arts is a must-see.
What are the best Airbnb and vacation rentals in Healdsburg, CA?
Which walking or cycling routes are the best in Healdsburg, CA?
For a scenic walk, try the Healdsburg Plaza to the Healdsburg Museum. For cycling, the Healdsburg to Windsor bike path is a popular choice, offering 11 kilometres of flat, paved trail along the Russian River. The Healdsburg area also has many great mountain biking trails in the surrounding hills.
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 place for outdoor activities. You can go hiking in the nearby mountains, kayaking on the Russian River, or play golf at one of the many courses in the area. There's also horseback riding, fishing, and even hot air ballooning available.
What are the best vacation rentals with a pool in Healdsburg, CA?
What other towns or cities can be easily accessed from Healdsburg, CA?
Healdsburg is well-positioned for exploring the region. You can easily reach the charming town of Guerneville to the west, or head north to the historic town of Cloverdale. For a bigger city experience, Santa Rosa is a short drive away, offering shopping, dining, and cultural attractions.
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 offer a wide range of amenities. Most have kitchens, bathrooms, and bedrooms, and many also have outdoor spaces like patios or decks. You'll often find amenities like Wi-Fi, laundry facilities, and even hot tubs or swimming pools.
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?
The best time to visit Healdsburg depends on your interests. Spring and autumn offer mild weather and beautiful scenery, while summer is popular for outdoor activities and wine tasting. If you prefer a quieter experience, winter can be lovely, with less crowds and the chance to enjoy the area's cozy atmosphere.
What are the local dishes in Healdsburg, CA region?
Healdsburg is known for its farm-to-table cuisine, with fresh, seasonal ingredients. You'll find plenty of restaurants serving delicious dishes like Sonoma County lamb, fresh seafood, and locally grown produce. Don't forget to try the local wines, from the renowned Pinot Noirs to the unique Zinfandels.
Destinations nearby
Best Healdsburg, CA holiday rentals with a balcony
10 5 reviews
Healdsburg, CA
08/07 – 10/07
SG$1209/nighttotal: SG$2418 (2 )
Luxe Healdsburg 3br Home + Comp Ridge Wine Tasting
3 2
apartment , Healdsburg
This Healdsburg holiday home is situated within 1.6km of Ridge Vineyards - Lytton Springs and Mazzocco Winery, and within 4.8km of Simi Winery and SingleThread Farm. The 106-square-metre property boasts four bedrooms, three bathrooms, sleeps eight guests, and includes a fully equipped kitchen, Jacuzzi, private garden, and free Wi-Fi.
9.8 37 reviews
Healdsburg, CA
07/09 – 11/09
SG$1950/nighttotal: SG$7800 (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 68 reviews
Healdsburg, CA
08/07 – 10/07
SG$3114/nighttotal: SG$6228 (2 )
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 Mins To Healdsburg
5 2
apartment , Healdsburg
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.
9.4 76 reviews
Healdsburg, CA
19/08 – 24/08
SG$829/nighttotal: SG$4145 (5 )
Cottages At Little Saint
1 2
resort , Healdsburg
Cottages At Healdsburg is situated in the heart of Healdsburg, just a short walk from the Raven Performing Arts Theater and Russian River, close to the Healdsburg Center for the Arts and Healdsburg Plaza. The resort consistently receives excellent guest ratings for its location, cleanliness, and overall experience. Each cottage comfortably accommodates two guests and features a private pool, fireplace, and furnished balcony. Guests can enjoy a seasonal outdoor pool, free Wi-Fi, concierge services, and a restaurant on-site, along with a range of other amenities and activities.
Best pet friendly Healdsburg, CA holiday rentals
Among the 114 accommodations in Healdsburg, CA, here are the 4 best pet friendly rentals
9.8 195 reviews
Healdsburg, CA
02/10 – 07/10
SG$2439/nighttotal: SG$12195 (5 )
Secluded Vineyard Estate Healdsburg
4 4
house , Healdsburg
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.
8.9 427 reviews
Healdsburg, CA
19/08 – 24/08
SG$177/nighttotal: SG$885 (5 )
A Grass-roofed Earthen Hobbit Hut
1 2
cabin , Geyserville
Isis Oasis Sanctuary is situated in Geyserville, a short 10-kilometre drive from the renowned Healdsburg and the Russian River. This unique B&B offers a cob hut crafted by sculptor Miguel Elliott, a spiritual retreat atmosphere, and a community garden, as well as a spacious dining pavilion with a fireplace and a small library.
Healdsburg, CA
20/08 – 23/08
SG$722/nighttotal: SG$2166 (3 )
Bermudes Family Vineyard View Healdsburg House
1 3
apartment , Healdsburg
This vineyard apartment in Healdsburg's Alexander Valley offers a unique stay, situated just 8 kilometres from Healdsburg town square and a short walk from Jordan Winery. This property accommodates up to six guests across two bedrooms and a rec room with Murphy beds, featuring an upgraded kitchen, air conditioning, Wi-Fi, and expansive outdoor space for dining and barbecuing with vineyard views.
10 130 reviews
Healdsburg, CA
02/10 – 07/10
SG$2823/nighttotal: SG$14115 (5 )
Tandatula, Wine Country Sanctuary With Pool, Hot Tub, Bocce, Fire Pits And More!
4 4
apartment , Healdsburg
This Healdsburg holiday home, situated in the Dry Creek Valley of Northern Sonoma County, is an hour's drive (approximately 80km) north of San Francisco and minutes from Dry Creek Vineyard and Healdsburg's attractions. This 288-square-metre property comprises a main house, cottage, and studio, sleeping up to 10 guests, and boasts a pool, hot tub, tennis court, fitness centre, and 1.25 acres of landscaped grounds with vineyards, offering bocce ball, croquet, and a games barn.