
Healdsburg Vacation Rentals
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Healdsburg vacation rentals

9.2 out of 10, Wonderful, (133 reviews)
The price is ¥16,604
¥18,928 total
includes taxes & fees
Sep 28 - Sep 29

2. Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Vineyard View Retreat • Fire Pit • Wine Tasting PerksHealdsburg
9.8 out of 10, Exceptional, (17 reviews)
The price is ¥26,900
¥62,830 total
includes taxes & fees
Sep 23 - Sep 24

3. Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/CForestville
10.0 out of 10, Exceptional, (6 reviews)

4. Riverbend Retreat - Hot Tub and Tastings Included
Riverbend Retreat - Hot Tub and Tastings IncludedHealdsburg
9.6 out of 10, Exceptional, (5 reviews)
The price is ¥53,371
¥147,218 total
includes taxes & fees
Sep 23 - Sep 24

5. Tranquil Redwood Retreat
Tranquil Redwood RetreatGuerneville
8.8 out of 10, Excellent, (13 reviews)
The price is ¥23,720
¥54,020 total
includes taxes & fees
Sep 23 - Sep 24

6. Enchanting Retreat in the heart of Redwoods
Enchanting Retreat in the heart of RedwoodsGuerneville
8.4 out of 10, Very good, (15 reviews)
The price is ¥22,026
¥50,555 total
includes taxes & fees
Sep 28 - Sep 29

7. Country Carriage House in Downtown Geyserville, Vineyard Views
Country Carriage House in Downtown Geyserville, Vineyard ViewsGeyserville
10.0 out of 10, Exceptional, (5 reviews)
The price is ¥25,571
¥61,271 total
includes taxes & fees
Oct 8 - Oct 9

8. Rivers Breeze - Wine Tastings Included
Rivers Breeze - Wine Tastings IncludedHealdsburg
10.0 out of 10, Exceptional, (20 reviews)
The price is ¥51,846
¥146,212 total
includes taxes & fees
Sep 28 - Sep 29
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.
Find vacation rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Healdsburg Hotel Reviews

The Lodge at Healdsburg, Tapestry Collection by Hilton
10/10 Excellent
Find out more about Healdsburg
Search for holiday rentals in Healdsburg on Expedia! You can easily find your home rentals, villas, holiday apartments in Healdsburg using one of the methods below:
- View our selection of featured holiday rentals in Healdsburg
- Use the map to find apartments and other holiday homes in the Healdsburg neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday rentals in Healdsburg while they last
Look no further and take a look at our great range of rental properties in Healdsburg!
















































































