Healdsburg vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Healdsburg
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
SUPERHOST
Guesthouse in Healdsburg
Alexander Valley: Wine Lover and Cycling Paradise
The Finca Guest House is a beautiful modern & private unit, which offers country seclusion just a short hop into Healdsburg. Three private outdoor spaces for your use! Coffee patio, wine patio, goat patio--your choice! World-class biking out the door. Guest House will be thoroughly cleaned per Airbnb guidelines!
*This property has farm animals so no outside animals allowed. See Rules and Policies notes
Gas grill w/burner is available for outdoor cooking. NO full kitchen.
Sonoma Co. TOT#3191N
$189 per night
SUPERHOST
Farm stay in Healdsburg
Gracianna Winery Vineyard Loft - Farm Stay
You will notice costs vary throughout the year based on availability.
Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile in Healdsburg includes equipped kitchen.
House truth: Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. It can be disruptive to sleep (or not, some say it wasn't a bother).
LOFT AVAILABLE BUT TASTING ROOM CLOSED DECEMBER 1 - MARCH 31.
TOT #3294N
$259 per night
SUPERHOST
Rental unit in Healdsburg
Downtown Healdsburg Perch
Set on the top floor of a Quonset Hut arched steel building, this location is high in style yet warm and inviting. A luxurious stay for two in a one-of-a-kind venue, plus the comforts of a kitchenette, cozy living room, spacious and spa-like bathroom, and quiet bedroom, all set above Healdsburg’s main street. A world-class gallery sits on the ground floor, and your home away from home is surrounded by rooftop bars, fine dining restaurants, tasting rooms, and shops.
$550 per night
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Healdsburg vacation rentals
Healdsburg home rentals
Healdsburg cottage rentals
Frequently Asked Questions
Are there family-friendly vacation rentals in Healdsburg?
Are there family-friendly vacation rentals in Healdsburg?
Yes! We have over 10 homes with more than 2 bedrooms perfect for families looking for a comfortable and convenient stay in Healdsburg.
How much does it cost to stay in an apartment in Healdsburg?
How much does it cost to stay in an apartment in Healdsburg?
Experience the best of Healdsburg with our apartment vacation rentals, averaging about $520 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Healdsburg?
Are there pet-friendly vacation rentals in Healdsburg?
Yes! Four-legged friends are welcome too! Select from over 40 pet-friendly vacation rentals in Healdsburg, so your furry family members can join in on the adventure.
Are there vacation rentals with a dedicated workspace in Healdsburg?
Are there vacation rentals with a dedicated workspace in Healdsburg?
Yes! Work meets play with ease at over 60 vacation rentals in Healdsburg featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Healdsburg vacation rentals on Airbnb with pools?
Are there Healdsburg vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Healdsburg, available on Airbnb. Make a splash and soak up the sun in style!
Do houses in Healdsburg have Air Conditioning?
Do houses in Healdsburg have Air Conditioning?
Absolutely! We offer over 50 house vacation rentals with Air Conditioning in Healdsburg. Enjoy a tailored experience with all the comforts you desire.