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Healdsburg, California, United States of America

Healdsburg house rentals

We found 542 houses — enter your dates for availability

Explore Healdsburg house rentals

Sun-Soaked Private Vineyard Haven with Firepit, Fireplace & Outdoor Oasis

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
$340 avg/night
(62)

Elegant - Peaceful - Romantic - Private

Sleeps 2 · 1 Bedroom · 1 Bathroom
$185 avg/night
(172)

Healdsburg Hilltop Retreat :: Craftsman detail, modern comforts & stunning VIEWS

Sleeps 6 · 2 Bedrooms · 2 Bathrooms
$255 avg/night
(97)

Historic Guest House on Plaza Street

Sleeps 2 · 1 Bedroom · 1 Bathroom
$135 avg/night

Dry Creek Cottage - Healdsburg

Sleeps 4 · 1 Bedroom · 1 Bathroom
$295 avg/night
(63)

Wooded Restful Retreat, with broad scenic views, outdoor dining

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
$295 avg/night
(154)

Search 542 houses

Recent reviews of Healdsburg house rentals
Stayed Jul 2021

Beautiful Lookout

This unique home is in a beautiful, private location right near the Russian River and was the perfect size for our family. There was plenty of space for our 2 young children, infant, and dog. It has a beautiful view and the host (who was very graciou...

Summer H.
Summer H.
Stayed Jul 2021

Great Place and location - loved it

The house was great and though the temperature was very hot during the day there were ample fans and even an air conditioner in the living room. Easy access to the river which had plenty of water and even some deep pools where you couldn't even touch...

jane c.
jane c.
Stayed Jul 2021

Idyllic Cabin in the Vineyards!

The cabin is perfect for a peaceful, relaxing time in the middle of beautiful vineyards in the Dry Creek Valley. It is furnished with everything you could possibly want (except maybe a fireplace!). The hosts are accommodating and responsive to your n...

Judith M.
Judith M.
Stayed Jul 2021

Great Location

The location is primo, just a short few blocks to downtown Healdsberg. The cottage was very clean and the bed was comfortable. However, we found that having only 2 small cups for coffee was simply not enough. It should also be noted that Grandma like...

Paolo S.
Paolo S.
Stayed Jul 2021

As Beautiful As Advertised

The cottage is spacious, comfortable, and had all of the necessary supplies for an enjoyable stay. It's also very close to the center of Healdsburg, while still giving you the country charm. What more could you want? This property sits on a beautiful...

Jonathan D.
Jonathan D.
Stayed Jul 2021

Wine country getaway

Lovely (small) guest house across the pool from owners of the property. Close to everything in Healdsburg. Great wine tasting, restaurants, biking, and hiking all nearby. Not walking distance to town but short car ride. Convenient to Highway 101 (but...

Dan E.
Dan E.

Connecticut, USA

Stayed Jul 2021

Favorite getaway in wine country

We've stayed at Casa Chiquita with our closest friends on several occasions now, and continue to look forward to the next time we can book again. The communication has always been responsive and the property manager has been very accessible regarding...

Fontaine S.
Fontaine S.
Stayed Jun 2021

A sweet cabin get away!

What a delightful stay we had! The cabin was clean, private, and perfectly situated in a quiet, romantic garden. We hardly saw anyone else the whole weekend. There was a side deck with a special "wind tunnel" effect that we got as a refreshing surpr...

Amy S.
Amy S.

Berkeley, CA

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