Best Vacation rentals and Airbnb offers in Healdsburg, CA
9.2 64 reviews
Healdsburg, CA
07/10 – 07/13
$559/nighttotal: $1677 (3 )
Mountain Cottage Near Russian River, Hiking & Downtown, Family And Pet Friendly
3 2
cottage , Healdsburg
This charming cottage is located just a short walk from the Russian River and a 10-minute drive from downtown Healdsburg, offering a peaceful retreat surrounded by redwood trees and mountain views. Reviewers consistently rate this rental "excellent" for its comfortable accommodations and convenient location. This 3-bedroom, 2-bathroom home comfortably sleeps 6 guests and offers 1100 square feet of living space. Enjoy modern amenities like a fully equipped kitchen, a relaxing spa, a private garden, and a spacious deck with a BBQ grill, perfect for enjoying meals and relaxing in the fresh air.
9.5 208 reviews
Healdsburg, CA
10/02 – 10/07
$497/nighttotal: $2485 (5 )
Serene Riverfront Cottage In Healdsburg Views Kayaks 1 5 Mile To Downtown
2 4
house , Healdsburg
Redwood River Lodge is located in Healdsburg, just 14 miles from the Luther Burbank Center for the Arts and 11 miles from Charles M. Schulz Sonoma County Airport. The lodge has earned excellent ratings from previous guests for its cleanliness, location, and overall experience. The two-bedroom, one-bathroom home spans 1190 square feet and comfortably accommodates six guests. Enjoy a fully equipped kitchen, private parking, and a range of amenities including a jacuzzi, a tennis court, and a garden.
9.9 292 reviews
Healdsburg, CA
10/02 – 10/07
$600/nighttotal: $3000 (5 )
The Wine Ranch
3 4
apartment , Healdsburg
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.
10 63 reviews
Healdsburg, CA
07/08 – 07/10
$382/nighttotal: $764 (2 )
The Roost - Garden Studio
1 2
house , Healdsburg
The Garden Room studio is centrally located in Healdsburg, one block from the Plaza, offering easy access to Healdsburg's restaurants and wineries. This one-bedroom, one-bathroom unit sleeps two guests and features a kitchen with a refrigerator, air conditioning, a garden, a fitness center, parking, and excellent guest ratings; enjoy its unique, handcrafted décor and peaceful atmosphere.
9.8 50 reviews
Healdsburg, CA
09/07 – 09/11
$535/nighttotal: $2140 (4 )
Rivers Breeze - Wine Tastings Included
3 2
apartment , Healdsburg
This charming riverfront cabin is just a short 3.5-mile drive from the Healdsburg Plaza and within a 5-minute drive of local farms, offering a peaceful escape from the hustle and bustle of town. The cabin has received excellent ratings for its location, cleanliness, and overall experience. The cozy apartment features 3 bedrooms and 2 bathrooms, comfortably accommodating up to 6 guests. Enjoy the rustic charm, access to kayaks, a spacious outdoor area, a well-equipped kitchen, and a convenient location near local attractions.
9.8 99 reviews
Healdsburg, CA
10/02 – 10/07
$876/nighttotal: $4380 (5 )
Dry Creek Ranch ~ (Tariff Discount) Hot Tub & Pool
3 4
apartment , Healdsburg
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.
9.9 106 reviews
Healdsburg, CA
08/19 – 08/24
$681/nighttotal: $3405 (5 )
Downtown Healdsburg Nest
2 2
apartment , Healdsburg
This Healdsburg apartment rental is located two blocks from the Healdsburg Plaza, offering easy access to downtown restaurants, shops, and tasting rooms. The two-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchen with modern appliances, a private patio, in-unit laundry, and high-speed internet; street parking is available on a first-come, first-served basis.
9.8 133 reviews
Healdsburg, CA
07/10 – 07/13
$1418/nighttotal: $4254 (3 )
Haven With Pool, Hot Tub And Tastings Included
2 2
house , Healdsburg
Private Vineyard Haven is located in Healdsburg, California, just a short drive from the Charles M. Schulz Sonoma County Airport and the Luther Burbank Center for the Arts. The property has earned excellent ratings for its location, cleanliness, and overall user experience. This 2-bedroom house features a fully equipped kitchen, air conditioning, and a private patio and balcony with mountain views. Guests can enjoy amenities like a swimming pool, Jacuzzi, tennis court, and a spa, as well as nearby cycling trails and easy access to local attractions.
9.5 207 reviews
Healdsburg, CA
07/08 – 07/10
$900/nighttotal: $1800 (2 )
River View Lodge - Hot Tub And Tastings Included
3 2
house , Healdsburg
River View Lodge is located near Healdsburg, offering beachfront access and mountain views, approximately 14 miles from the Luther Burbank Center for the Arts. This house has consistently received excellent ratings for its location, cleanliness, and overall user experience. The home features three bedrooms and can comfortably accommodate up to eight guests. Amenities include a fully equipped kitchen, a hot tub, a terrace, a garden, a spa, a tennis court, and free parking.
9.8 143 reviews
Healdsburg, CA
09/07 – 09/11
$317/nighttotal: $1268 (4 )
Healdsburg 2br Cottage With Private Yard!
1 2
apartment , Healdsburg
This charming guesthouse is located just a short drive from Healdsburg Plaza, offering easy access to the town's shops, restaurants, and wineries. The home has consistently received excellent ratings for its cleanliness, location, and overall experience. The guesthouse has two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy the modern amenities, including a Nespresso coffee maker, Parachute towels, and Evenfall hemp linens, as well as the private yard with a separate gated entrance.
10 4 reviews
Healdsburg, CA
07/08 – 07/10
$304/nighttotal: $608 (2 )
The Roost - Sun Room
1 2
apartment , Healdsburg
This Healdsburg apartment rental is conveniently located near the Raven Performing Arts Theater, Healdsburg Center for the Arts, and the Healdsburg Museum, with Healdsburg Plaza and Pezzi King Winery a short 15-minute drive away. The one-bedroom, one-bathroom unit sleeps two guests and includes amenities such as air conditioning, Wi-Fi, a balcony, a hair dryer, and an iron/ironing board.
9.9 611 reviews
Healdsburg, CA
10/02 – 10/07
$553/nighttotal: $2765 (5 )
Healdsburg Cottage Walk To The Plaza, Workspace
1 4
cottage , Healdsburg
This charming Healdsburg cottage is located within walking distance of the Healdsburg Museum, Russian River, and downtown Healdsburg, offering easy access to shops, restaurants, and attractions. The cottage boasts excellent ratings for location, cleanliness, and user experience. This cozy home offers a comfortable 600 square feet of space with one bedroom, one bathroom, and a capacity for four guests. The cottage is equipped with a fully equipped kitchen, a private yard, a spa, a tennis court, and a variety of other amenities for a relaxing and enjoyable stay.
Compare Vacation Rentals for Families in Healdsburg, CA
These family-friendly vacation rentals in Healdsburg, CA offer spacious layouts and easy access to top city attractions.
9.6 19 reviews
Healdsburg, CA
07/10 – 07/13
$1813/nighttotal: $5439 (3 )
Healdsburg Homestead With Pool, Hot Tub And Tastings Included
3 2
apartment , Healdsburg
This family-friendly vacation home in Healdsburg is surrounded by vineyards and is just a short drive from popular attractions like Krug Event Center and Seghesio Family Vineyards. Guests have rated it as "excellent". The house has 3 bedrooms, 2 bathrooms, and can accommodate up to 7 guests. It has a floor area of 1700 square feet. The house features a private pool, a fenced private yard, a fireplace, an upscale kitchen, free WiFi, a spa tub, barbecue grills, and housekeeping on request. Guests can also enjoy activities like swimming, sunbathing, grilling, and relaxing in the spa tub.
10 1 review
Healdsburg, CA
08/19 – 08/24
$570/nighttotal: $2850 (5 )
Windsor Home With Sauna & Outdoor Fire Pit
3 2
apartment , Windsor
This Windsor apartment is located a short drive from the Windsor Town Green, Russian River, and Sonoma County wineries. This 1800 sq ft home offers 3 bedrooms, 2 bathrooms, and can accommodate up to 8 guests with amenities including air conditioning, Wi-Fi, a full kitchen, BBQ grill, fire pit, private sauna, and ice bath.
10 85 reviews
Healdsburg, CA
10/02 – 10/07
$1801/nighttotal: $9005 (5 )
Alexander Valley Modern Farmhouse With Vintage Charm - Newly Renovated Pool
3 4
apartment , Healdsburg
This Healdsburg vacation rental is located near the Russian River, about 1.5 km from Jordan Vineyard & Winery and within 5 km of other renowned wineries. The property has excellent user, location, and cleanliness ratings. The 3-bedroom, 4-bathroom home features a spacious 2950 square feet layout. Enjoy a private pool, a fenced yard, a barbecue grill, a fireplace, a fully equipped kitchen, a fitness center, a garden, and a bar.
10 5 reviews
Healdsburg, CA
08/20 – 08/23
$523/nighttotal: $1569 (3 )
The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !
2 3
apartment , Healdsburg
This Dry Creek Road cottage is located in Healdsburg's wine country, one mile from downtown Healdsburg's tasting rooms and restaurants, and within walking distance of many wineries. The two-bedroom, two-bathroom barn-style rental sleeps five, features a private hot tub, fenced yard, Tesla charging station, and custom interior with hardwood floors and tiled showers.
Best Healdsburg, CA vacation rentals with parking
10 121 reviews
Healdsburg, CA
09/07 – 09/11
$1790/nighttotal: $7160 (4 )
Luxury Retreat W/ Pool, Hot Tub & Sauna
1 2
apartment , Healdsburg
This private vineyard estate is located in the rolling hills of the Dry Creek Valley, just minutes from the Healdsburg Plaza and famed Dry Creek and Alexander Valley Vineyards. The three-bedroom, three-bathroom villa boasts a modern design with comfortable furnishings, a gourmet kitchen, a spacious deck, and a luxurious spa, sauna, and fire pit.
10 221 reviews
Healdsburg, CA
07/08 – 07/10
$1055/nighttotal: $2110 (2 )
Wake Up In Your Own Private Vineyard - Healdsburg
3 2
apartment , Healdsburg
This private home is just minutes from downtown Healdsburg, nestled in a serene setting surrounded by vineyards and offering easy access to world-class wineries. It has consistently received excellent ratings for its location, cleanliness, and overall experience. This spacious 3-bedroom, 2-bathroom home can comfortably accommodate up to 6 guests. The fully equipped kitchen, outdoor terrace, and private garden provide ample space for relaxation and entertaining, while the vineyard views and proximity to downtown Healdsburg offer the perfect blend of tranquility and convenience.
10 38 reviews
Healdsburg, CA
07/10 – 07/13
$1376/nighttotal: $4128 (3 )
Vineyard Vue - Wine Tastings Included
3 2
apartment , Healdsburg
This Healdsburg vacation home is located within easy walking distance of the Healdsburg Plaza, Healdsburg Center for the Arts, and Healdsburg Museum, making it a great spot to explore the town's cultural offerings. Guests have consistently rated this property excellent. This 3-bedroom, 4-bathroom rental comfortably sleeps 6 guests and features a spacious 1700 square foot layout. Enjoy a private garden, a relaxing spa, a tennis court, and a fully equipped kitchen, making it easy to entertain friends and family.
10 6 reviews
Healdsburg, CA
07/10 – 07/13
$3713/nighttotal: $11139 (3 )
Stunning Dry Creek Road Estate
4 2
apartment , Healdsburg
This beautiful home is located in the Dry Creek Valley, just 8 minutes from Healdsburg's town square, offering a peaceful escape with stunning views. Guests consistently rate this property excellent for its location, cleanliness, and overall experience. The 4200 square foot home comfortably accommodates up to 10 guests in its four bedrooms. Enjoy a relaxing getaway with amenities like a heated pool, jacuzzi, and a spacious terrace, perfect for enjoying the beautiful California weather.
Frequently Asked Questions about vacation rentals in Healdsburg, CA
What are some interesting places to visit in or near Healdsburg, CA?
Healdsburg is a gem! You've got the Healdsburg Plaza, filled with charming shops and restaurants. If you're into wine, the Russian River Valley is just a short drive away, with wineries like J Vineyards & Winery and Ferrari-Carano Vineyards & Winery. And for a nature escape, head to the Armstrong Redwoods State Natural Reserve, with its towering redwood trees.
What are the best Airbnb and vacation rentals in Healdsburg, CA?
Which walking or cycling routes are the best in Healdsburg, CA?
The Healdsburg Downtown Walking Tour is a great way to explore the historic area. For cycling, the Healdsburg to Sebastopol bike path is a scenic 12-mile ride along the Russian River. You can also try the Healdsburg to Windsor bike path for a more challenging route.
What are the most popular Airbnbs in Healdsburg, CA?
What other towns or cities can be easily accessed from Healdsburg, CA?
From Healdsburg, you can easily reach Santa Rosa and Petaluma by car, both within a 30-minute drive. For a longer trip, you can head to San Francisco which is about a 1.5-hour drive.
What are the best vacation rentals with a pool in Healdsburg, CA?
What amenities are commonly available in vacation rentals in Healdsburg, CA?
Most vacation rentals in Healdsburg offer amenities like private pools, hot tubs, and outdoor grilling areas. Many also have fully equipped kitchens, laundry facilities, and high-speed internet. Some even have fireplaces and game rooms for extra entertainment.
What are the best rentals for families and kids in Healdsburg, CA?
What time of year is best to rent a vacation rental Healdsburg, CA?
Healdsburg is beautiful year-round, but the best time to visit is during the spring and fall. The weather is mild, the crowds are smaller, and the wineries are in full swing. Summer can be hot, and winter can be rainy, but it's still a great time to visit if you enjoy the cooler weather.
What are the best rentals or Airbnbs with a jacuzzi in Healdsburg, CA?
Choose the Right Vacation Rentals with a Terrace in Healdsburg, CA
Start your morning right with a vacation rental in Healdsburg, CA featuring a private balcony and stunning views.
10 14 reviews
Healdsburg, CA
07/10 – 07/13
$768/nighttotal: $2304 (3 )
Healdsburg Victorian Cottage On Vineyard Estate
2 2
apartment , Healdsburg
This 1895 Victorian cottage is located in Alexander Valley wine country, 1.3 miles from Healdsburg Plaza's tasting rooms and restaurants, and within walking distance to Tongue Dancer Wines (0.4 miles) and Arnot-Roberts (0.8 miles). This 1670 square foot rental sleeps 4 guests in 2 bedrooms and 2 bathrooms, featuring a modernized kitchen with a marble island and induction oven, air conditioning, internet, a terrace, garden, and parking for 2 vehicles.
Healdsburg, CA
09/07 – 09/11
$1302/nighttotal: $5208 (4 )
Modern Wine Country Home On 10 Acres With Vineyard
3 2
house , Healdsburg
This 3-bedroom Healdsburg villa is located 5 miles from Healdsburg Plaza and 12 miles from Charles M. Schulz–Sonoma County Airport, offering easy access to attractions like Safari West and Petrified Forest within a 25-mile radius. The 10-acre property features a vineyard with stunning views, a fully equipped kitchen, a private balcony, free Wi-Fi, parking, and accommodates up to 11 guests.
9.3 270 reviews
Healdsburg, CA
09/07 – 09/11
$458/nighttotal: $1832 (4 )
Rockhouse Suites
1 2
studio , Healdsburg
Situated in the heart of Healdsburg, Rockhouse Suites is a 3-star hotel with excellent user ratings for its location, cleanliness, and overall experience. It offers a convenient location within walking distance of Healdsburg Plaza and the Healdsburg Center for the Arts. The hotel features 800 square feet suites with one bedroom and one bathroom, accommodating up to two guests. Guests can enjoy amenities such as free breakfast, free self-parking, a smoke-free environment, free WiFi in public areas, a landscaped garden, and a concierge service.
Healdsburg, CA
07/08 – 07/10
$593/nighttotal: $1186 (2 )
Cottages At Little Saint
1 2
resort , Healdsburg
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.
Discover Pet-Friendly Vacation Rentals in Healdsburg, CA
Traveling with pets? These dog-friendly vacation rentals and Airbnbs in Healdsburg, CA are steps away from dog parks and city walks.
9.4 31 reviews
Healdsburg, CA
10/02 – 10/07
$526/nighttotal: $2630 (5 )
Heart Of Wine Country, Cute Cottage W/hot Tub\n
3 4
apartment , Windsor
This charming cottage is located in a quiet creekside setting in Windsor, just a short walk from the downtown area and a quick drive to Healdsburg. It has received excellent user ratings, making it a popular choice for travelers. The cottage has three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy a relaxing stay with amenities like a Jacuzzi, a private terrace, and a fully equipped kitchen, plus plenty of opportunities for outdoor activities and exploring the local attractions.
9.8 132 reviews
Healdsburg, CA
08/19 – 08/24
$670/nighttotal: $3350 (5 )
Riverside Cottage: Access And River Views- 1 Miles From Downtown Healdsburg
2 2
apartment , Healdsburg
This charming cottage is situated on South Fitch Mountain, just a short 6-minute drive from Healdsburg's downtown Plaza and offers beautiful river views. The property has earned excellent ratings for its location, cleanliness, and overall experience. The house comfortably accommodates up to 6 guests in its two bedrooms and features a fully equipped kitchen with modern appliances. Enjoy the peace and tranquility of the riverfront location with a wraparound porch, hot tub, and a variety of entertainment options including a Smart TV, a Sony CD/DVD player, and a Bluetooth sound system.
10 14 reviews
Healdsburg, CA
10/02 – 10/07
$1022/nighttotal: $5110 (5 )
Family-friendly Dry Creek Valley Retreat W/amazing Views <15 Minutes To Square
3 4
apartment , Healdsburg
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.
10 68 reviews
Healdsburg, CA
07/08 – 07/10
$2422/nighttotal: $4844 (2 )
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 Mins To Healdsburg
5 2
apartment , Healdsburg
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.