Healdsburg Vacation Home Rentals from CA $514: Search Top Private Vacation Homes for Rent

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

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Our top choices for Healdsburg vacation homes

1. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Northwest Santa Rosa

kevin c.

CA $514 total

includes taxes & fees

Oct 13 - Oct 14

A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

2. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Healdsburg

Riley F.

CA $713 total

includes taxes & fees

Oct 29 - Oct 30

A wooden deck with two Adirondack chairs, a small table, and a sign indicating 'SANTA CLARA.'

3. Russian River Retreat: Private Beach & DogFriendly

Forestville

Anna K.

CA $962 total

includes taxes & fees

Oct 11 - Oct 12

A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

4. Wine Country Cottage Escape

Fulton

Tina A.

CA $531 total

includes taxes & fees

Oct 12 - Oct 13

A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

5. Wildflower

Windsor

Keri S.

CA $1,464 total

includes taxes & fees

Oct 12 - Oct 13

A modern house with a deck, outdoor seating, and a large glass door leading to an interior space.

6. Private Vineyard Haven with Pool, Hot Tub and Tastings Included

Healdsburg

Rock R.

CA $2,103 total

includes taxes & fees

Nov 3 - Nov 4

A patio with outdoor seating, a hot tub, and string lights.

7. Healdsburg Plaza Gem-Hot Tub and Tastings Included

Healdsburg

Christopher T.

CA $1,882 total

includes taxes & fees

Oct 12 - Oct 13

An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

8. Russian River Brew-cation Home

Northwest Santa Rosa

Gina N.

CA $733 total

includes taxes & fees

Oct 12 - Oct 13

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Top Healdsburg Hotel Reviews

Grape Leaf Inn

10/10 Excellent

"Staff was great. Breakfast was very good. Wine and cookies in the afternoon a nice touch. Best though several wineries included for free tastings. Great value overall"

Appellation Healdsburg

8/10 Good

"The property itself is really nicr, but the restaurant was incredibly disappointing, and the staff — while friendly — were not remotely knowledgeable about the area or the hotel itself. How late is the hot tub open? “Great question, no idea.” Can we get a second ice bucket? “Not sure if we can do that.” Where is there a nice walking trail nearby? “I think the closest one is like 40 minutes away.” (Spoiler: there were multiple within 5-10 min) So if you’re looking for a relaxing, beautiful place to stay and don’t intend to eat on property or ask the staff any questions, this is the place for you!"

Find out more about Healdsburg

Healdsburg Vacation Homes information

Number of reviews	648
Accommodation	219 Vacation Homes
Lowest Price	CA $514
Highest Price	CA $7,816

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Healdsburg vacation homes

1. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

2. Vineyard View Retreat • Fire Pit • Wine Tasting Perks