A garden pathway lined with white roses leading to a building with a stone facade and a window.

Search and Rent Healdsburg Condos

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Healdsburg condo rentals

Outdoor pool, a heated pool

Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6

Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6
Windsor
10.0 out of 10, Exceptional, (1 review)
$337 nightly
The price is $373
Jul 5 - Jul 6
Total with taxes and fees
Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6
A heated pool

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Windsor
9.2 out of 10, Wonderful, (47 reviews)
"Nice location to base from when visiting multiple wineries in the area. Fit our needs well with 2 bedrooms plus the murphy bed. Pool and hot tub were nice as well. I don't need the long sell on attending a hotel club event and having to pay for wifi if you wanted it doesn't seem right in 2026."
United States
Matthew G.
$337 nightly
The price is $373
Jul 5 - Jul 6
Total with taxes and fees
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Outdoor pool, a heated pool

TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6

TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6
Windsor
$337 nightly
The price is $373
Jul 5 - Jul 6
Total with taxes and fees
TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6
Outdoor pool, a heated pool

One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6

One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6
Windsor
$337 nightly
The price is $373
Jul 5 - Jul 6
Total with taxes and fees
One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6
Outdoor dining

Romantic Wine Country Retreat with Hot Tub

Romantic Wine Country Retreat with Hot Tub
Boyes Hot Springs
9.8 out of 10, Exceptional, (53 reviews)
"This is a beautiful property with outstanding hosts. I’ll definitely be returning. "
United States
Erin B.
$300 nightly
The price is $332
Jul 13 - Jul 14
Total with taxes and fees
Romantic Wine Country Retreat with Hot Tub
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Healdsburg Hotel Reviews

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

10/10 Excellent
"Clean room, great staff, wonderful ambience. In a great location as well. Highly recommend as a great bang for your buck!"
Hunter 2-night trip
Posted less than an hour ago
Dry Creek Inn MOD Collection by Sonesta

Find out more about Healdsburg

Healdsburg Condo Rentals information

Number of reviews
100
Accommodation
24 Condo Rentals
Lowest Price
$332
Highest Price
$373

Frequently asked questions

How much do condos in Healdsburg cost?
The price range for condos in Healdsburg is $332 to $373 per night. No matter your budget, you're sure to find something that suits your needs — as well as your whole squad! These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Healdsburg?
Healdsburg has 24 condos. To help you find the ideal digs, use our filter tool to search for the amenities or perks you need.
Are there any family-friendly condos in Healdsburg?
If you're planning a trip to Healdsburg and after a family-friendly condo, consider Worldmark Windsor, Beautiful Wine Country 2bedroom 2bath Sleep6 Resort Condos. This 3-star option has a fireplace and a swimming pool. Once you've checked in and dropped off your bags, there are loads of family-friendly attractions to discover around Healdsburg. Armstrong Redwoods State Park and Francis Ford Coppola Winery guarantee fun for all ages.
Why book your condo in Healdsburg with Expedia?
We think that vacations should be a piece of cake, so if you're in search of condos at a competitive price, Expedia is here to help. Stick to the budget and stay in something small and cozy, or splurge on a 5-star condo and treat your loved ones. Take advantage of our search filters to find a stay in Healdsburg that meets your needs.
How can I find cheap condos in Healdsburg?
The easiest way to score cheap condos in Healdsburg is with Expedia's handy filter tool. Fine-tune your search results by amenities, budget and star rating to take advantage of awesome rates in just a few clicks.
What is there to do in Healdsburg near my condo?
Whatever your tastes or interests, Healdsburg has plenty to keep you on the hop. Healdsburg Golf Club, Pezzi King Winery and Soda Rock Winery are on many travelers' trip plans. Don't leave without exploring Wilson Winery, Matrix Winery and Healdsburg Plaza either. With Expedia's condo deals in Healdsburg, you can see even more fabulous attractions like these with the money you save.

Explore a world of travel with Expedia