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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.

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
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
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

Stay near Healdsburg's top sights

Healdsburg Plaza47 locals recommend
Safeway27 locals recommend
Healdsburg Veterans Memorial Beach5 locals recommend
Barndiva62 locals recommend
SingleThread Farm - Restaurant - Inn31 locals recommend
Bravas Bar de Tapas68 locals recommend

Healdsburg home rentals

Home in Healdsburg
Dry Creek w/Hot Tub, Bocce, Vineyard Views
$450 per night
Home in Healdsburg
Vineyard Overlook
$190 per night
Home in Healdsburg
C - Wineries/breweries seconds away
$151 per night
Home in Windsor
NEW Charming Windsor Home
$143 per night

Healdsburg cottage rentals

Cottage in Healdsburg
Luxurious, Private, Healdsburg Guest House
$373 per night
Cottage in Healdsburg
Luxury cottage on 30-acre Healdsburg vineyard
$595 per night
Cottage in Healdsburg
Bee Haven Cottage
$302 per night
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
$341 per night

Frequently Asked Questions

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?

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?

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?

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?

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?

Absolutely! We offer over 50 house vacation rentals with Air Conditioning in Healdsburg. Enjoy a tailored experience with all the comforts you desire.
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