Best Vacation Homes in Healdsburg
Cabin
10.0(331 Reviews)
1 Bedroom
1 Bath
2 Guests
840 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $280/Night
7 Nights - US $1,960
House
10.0(2 Reviews)
2 Bedrooms
3 Baths
4 Guests
2098.96 ft²
- Fireplace/Heating
Pool
Air Conditioner
Internet
US $1,979/Night
7 Nights - US $13,852
Bed & Breakfast
9.4(170 Reviews)
1 Bedroom
1 Bath
Spa- Pool
- Balcony/Terrace
Breakfast
US $302/Night
7 Nights - US $2,112
House
10.0(329 Reviews)
2 Bedrooms
2 Baths
4 Guests
1375 ft²
Oceanfront- Fireplace/Heating
Ocean View- Balcony/Terrace
US $448/Night
7 Nights - US $3,136
House
10.0(1 Review)
3 Bedrooms
4 Baths
6 Guests
1700.7 ft²
- Fireplace/Heating
View- Air Conditioner
- Internet
US $1,404/Night
7 Nights - US $9,830
House
10.0(239 Reviews)
3 Bedrooms
1 Bath
6 Guests
840 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
Pet Friendly
US $392/Night
7 Nights - US $2,744
House
10.0(161 Reviews)
2 Bedrooms
2 Baths
4 Guests
1300 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $722/Night
7 Nights - US $5,057
House
10.0(90 Reviews)
1 Bedroom
1 Bath
2 Guests
450 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $364/Night
7 Nights - US $2,548
Healdsburg Luxury Rentals
House
10.0(1 Review)
6 Bedrooms
6 Baths
12 Guests
Private Pool- Hot Tub
- Fireplace/Heating
- Pool
US $5,856/Night
7 Nights - US $40,995
Hotel
9.7(14 Reviews)
38 Baths
1296.05 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $5,030/Night
7 Nights - US $35,212
Villa
10.0(27 Reviews)
4 Bedrooms
4 Baths
8 Guests
4700 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $4,677/Night
7 Nights - US $32,736
House
5 Bedrooms
5 Baths
12 Guests
- Pool
- Kitchen
- Internet
Child Friendly
US $3,926/Night
7 Nights - US $27,485
House
10.0(24 Reviews)
4 Bedrooms
1 Bath
12 Guests
4000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $3,687/Night
7 Nights - US $25,809
House
10.0(1 Review)
6 Bedrooms
7 Baths
12 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $3,376/Night
7 Nights - US $23,634
House
9.0(2 Reviews)
6 Bedrooms
4 Baths
12 Guests
3000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $3,164/Night
7 Nights - US $22,146
House
10.0(6 Reviews)
4 Bedrooms
5 Baths
10 Guests
4200 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $3,004/Night
7 Nights - US $21,031
Healdsburg Pet Friendly Vacation Rentals
House
10.0(30 Reviews)
2 Bedrooms
3 Baths
6 Guests
2175 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,204/Night
7 Nights - US $8,428
House
10.0(1 Review)
3 Bedrooms
4 Baths
6 Guests
3648.97 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Parking
US $1,388/Night
7 Nights - US $9,716
RV Rental
9.0(106 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $149/Night
7 Nights - US $1,046
Cottage
10.0(22 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $494/Night
7 Nights - US $3,460
House
10.0(1 Review)
3 Bedrooms
2 Baths
7 Guests
1700.7 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Air Conditioner
US $1,346/Night
7 Nights - US $9,422
House
10.0(21 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $160/Night
7 Nights - US $1,121
House
10.0(18 Reviews)
2 Bedrooms
1 Bath
6 Guests
845 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $746/Night
7 Nights - US $5,225
House
10.0(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $277/Night
7 Nights - US $1,941
Healdsburg Large Vacation Homes
Villa
9.4(31 Reviews)
2 Bedrooms
2 Baths
6 Guests
1518 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $473/Night
7 Nights - US $3,309
House
9.5(2 Reviews)
6 Bedrooms
6 Baths
18 Guests
5005.22 ft²
- Fireplace/Heating
- Pool
- View
- Air Conditioner
US $1,735/Night
7 Nights - US $12,145
House
10.0(196 Reviews)
5 Bedrooms
6 Baths
12 Guests
4600 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
US $2,265/Night
7 Nights - US $15,856
Bed & Breakfast
9.4(112 Reviews)
6 Bedrooms
6 Baths
12 Guests
374.94 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $343/Night
7 Nights - US $2,401
House
10.0(160 Reviews)
4 Bedrooms
4 Baths
10 Guests
2200 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,788/Night
7 Nights - US $12,513
House
10.0(130 Reviews)
4 Bedrooms
3 Baths
10 Guests
3100 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,903/Night
7 Nights - US $13,319
House
10.0(117 Reviews)
4 Bedrooms
3 Baths
10 Guests
2800 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,830/Night
7 Nights - US $12,809
House
10.0(96 Reviews)
5 Bedrooms
6 Baths
10 Guests
3500 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,315/Night
7 Nights - US $9,204
Why Choose Rent By Owner for your Healdsburg Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Healdsburg
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here can enhance your experience, as seasonal variations in this destination influence everything from weather to local events, helping you select the perfect period for booking your vacation rentals in this charming region.
Peak Season Highlights
Summer (June to August)
During the summer months, this destination experiences warm weather ideal for outdoor activities and wine tasting experiences, making it a lively time for travelers seeking vibrant local events.
Average Temperature Daytime: 75-85°F - Nighttime: 50-60°F
Fall (September to November)
Autumn offers a stunning backdrop of colorful foliage, attracting visitors interested in harvest festivals and winery tours in the region.
Average Temperature Daytime: 70-80°F - Nighttime: 45-55°F
Off-Season Highlights
Winter (December to February)
The winter months bring cooler temperatures and a quieter atmosphere, perfect for those seeking a peaceful retreat away from the bustling crowds.
Average Temperature Daytime: 55-65°F - Nighttime: 35-45°F
Spring (March to May)
Spring heralds a period of renewal with blossoming vineyards and pleasant weather, offering a more relaxed experience before the busy summer season begins.
Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F
Weekly Weather Forecast for Healdsburg
How to Book Your Healdsburg Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Healdsburg
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor pool to unwind and relax in the sunshine.
- Spend time on a spacious patio equipped with seating and dining areas for outdoor gatherings.
- Relish a lush landscaped garden perfect for strolling or enjoying peaceful moments outside.
- Utilize a barbecue grill for hosting memorable cookouts in this inviting setting.
- Take advantage of a fire pit area ideal for cozy evenings under the stars.
- Benefit from outdoor lounging spaces that offer stunning views of the surrounding vineyards.
- Make use of well-maintained walking trails or bike paths nearby to explore the scenic countryside.
Top Attractions Around Healdsburg
What attractions are nearby?
Within this charming destination, you can explore a variety of activities such as wine tasting at renowned wineries, scenic outdoor pursuits in nearby parks, and culinary experiences that showcase the region’s acclaimed cuisine—all easily accessible from your vacation rental in Healdsburg.
Family Activities
- Healdsburg Museum and Historical Society: Explore the rich history of this charming region through engaging exhibits that offer educational family fun.
- Healdsburg Plaza Park: Enjoy a relaxing day outdoors at this scenic park, perfect for picnics, playground activities, and family strolls in the heart of town.
- Wells Fargo Center for the Arts: Experience family-friendly performances and cultural events that showcase local talent and bring everyone together.
- Russian River Adventures: Embark on gentle canoeing or kayaking trips suitable for families, allowing you to discover the area's natural beauty from the water.
Adult Activities
- Wine Tasting Tours: Explore prestigious vineyards and indulge in world-class wine tastings that showcase the region's renowned winemaking heritage.
- Gourmet Dining Experiences: Savor exquisite local cuisine at acclaimed restaurants, offering a taste of the region’s culinary excellence amidst charming surroundings.
- Art Galleries and Studios: Discover the area's vibrant arts scene by visiting boutique galleries and meeting local artists in their studios.
- Scenic Outdoor Activities: Enjoy leisurely hikes, cycling, or picnics in picturesque parks and lush countryside settings, perfect for relaxing days here.
Other Places to Stay in Healdsburg, CA
Krug Event Center
Hanna Winery and Vineyards
Pezzi King Winery
Healdsburg Plaza
Healdsburg Center for the Arts
Healdsburg Museum
Healdsburg Ridge Open Space Preserve
Raven Performing Arts Theater
Healdsburg District Hospital
Simi Winery
Tayman Park Golf Course
Healdsburg Golf Club
Healdsburg Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Wine Tours: Book your wine tasting experiences early to secure spots at popular wineries in the area and make the most of your visit here.
- Explore Local Cuisine: Take advantage of the region’s farm-to-table restaurants to enjoy authentic flavors unique to this destination.
- Discover Hidden Gems: Use local guides or recommendations to find lesser-known spots in here that offer a more intimate experience of the area.
- Experience the Scenic Outdoors: Schedule outdoor activities such as biking or walking along scenic trails to fully immerse yourself in the region's natural beauty.
Transportation Options
- Rental Cars: You can explore the region at your own pace with rental cars available nearby, providing a flexible way to visit vineyards and local attractions.
- Public Transportation: Local bus services offer convenient transit options for visitors looking to navigate this charming area without the hassle of driving.
- Taxi and Rideshare Services: Taxis and rideshare apps such as Uber and Lyft are readily accessible for quick, reliable transportation around here.
- Bike Rentals: Biking is an enjoyable way to experience the scenery at a leisurely pace, with bike rentals easily obtainable for exploring the region's scenic routes.
Local Customs Options
- Wine Tasting Etiquette: Respect local customs by Bulgari wine tasting, which is a cherished tradition that emphasizes savoring and appreciating the region’s renowned vineyards.
- Farmers' Market Traditions: Supporting local farmers’ markets in the area demonstrates your appreciation for the region’s fresh produce and sustainable practices.
- Recreational Winemaking: Participating in or observing traditional winemaking methods reflects the region’s deep-rooted heritage that visitors often find fascinating.
- Local Art Appreciation: Engaging with the area's vibrant art scene by visiting galleries and exhibits showcases the region’s commitment to nurturing its artistic community.
Healdsburg Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Healdsburg?
There are a lot of options in Healdsburg. If you plan on staying in the Healdsburg area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Healdsburg:
- ✨Rustic Cabin in Dry Creek Valley with beautiful views/5 miles to Plaza ✨
- Wooded Restful Retreat, with broad scenic views, outdoor dining
- Wine Country Retreat with Panoramic Views-5 min from downtown Healdsburg
- Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
- Private and Quiet Vineyard Villa with Hot Tub
- 5 BEDROOM, 6.5 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE
- Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza
- Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
- Renovated Vineyard Home - 4 BR/4 BA - Solar Pool, Spa, Views
- TandaTula, Wine Country Sanctuary with Pool, Hot Tub, Bocce, Fire Pits and More!
2. How many vacation rentals have private pools in Healdsburg?
There are 60 vacation rentals with private pools near Healdsburg. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Healdsburg are best for families?
If you are looking for a family-friendly vacation home in Healdsburg, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Healdsburg:
4. How many Rentbyowner vacation rentals are available in Healdsburg?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 346 in the Healdsburg area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Healdsburg.
5. What is the cancellation policy for vacation rentals in Healdsburg, California?
The cancellation policy varies depending on the property owner and listing. It is important to review the specific terms outlined in the listing details or contact the host directly for clarity on cancellation deadlines and any potential fees.
6. How do I ensure my booking in Healdsburg is secure and reliable?
Booking through verified listings with trusted hosts provides a secure experience. Make sure to read guest reviews, confirm the host's reputation, and communicate through the platform's messaging system for added security.
7. Are there restrictions or minimum stay requirements for accommodations here?
Yes, many properties in the area set minimum stay requirements or have specific restrictions. These details will be listed on each property page, so it’s best to verify these before completing your reservation.
8. What amenities can I expect from accommodations in this destination?
Amenities vary by property but typically include essentials like Wi-Fi, kitchen facilities, and parking. The listing descriptions will specify what amenities are offered, allowing you to select the best fit for your needs.
9. How do I get assistance if I encounter issues during my stay in Healdsburg?
In case of any problems, contact the property host directly through the platform for support. Additionally, the platform offers customer service to help resolve any concerns related to your booking or stay.
Healdsburg Top Rated Vacation Rentals
House
10.0(184 Reviews)
3 Bedrooms
2 Baths
8 Guests
2400 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,060/Night
7 Nights - US $7,417
House
10.0(105 Reviews)
3 Bedrooms
2 Baths
8 Guests
2100 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,231/Night
7 Nights - US $8,614
House
10.0(68 Reviews)
5 Bedrooms
4 Baths
10 Guests
4275 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,044/Night
7 Nights - US $14,308
House
10.0(63 Reviews)
5 Bedrooms
5 Baths
12 Guests
3800 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,651/Night
7 Nights - US $18,555
House
10.0(60 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,102/Night
7 Nights - US $7,714
House
10.0(41 Reviews)
3 Bedrooms
3 Baths
6 Guests
2950 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,787/Night
7 Nights - US $12,511
House
10.0(41 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,428/Night
7 Nights - US $9,996
House
10.0(38 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,378/Night
7 Nights - US $9,643
