Healdsburg Vacation Homes

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 holiday homes

A spacious living area with a large window, wooden ceiling beams, and a cozy seating arrangement.

1. ❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤

Healdsburg

sharon p.

HK$3,989 total

includes taxes & fees

21 Oct - 22 Oct

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

Mark R.

HK$3,568 total

includes taxes & fees

16 Nov - 17 Nov

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

Northwest Santa Rosa

kevin c.

HK$2,917 total

includes taxes & fees

1 Nov - 2 Nov

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

4. Russian River Retreat: Private Beach & DogFriendly

Forestville

Anna K.

HK$5,275 total

includes taxes & fees

18 Oct - 19 Oct

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

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

Healdsburg

Rock R.

HK$11,440 total

includes taxes & fees

3 Nov - 4 Nov

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

6. Wine Country Cottage Escape

Fulton

Tina A.

HK$2,908 total

includes taxes & fees

27 Oct - 28 Oct

A deck with outdoor seating, hot tubs, and a glass door leading to a forested area.

7. River View Lodge - Hot Tub and Tastings Included

Healdsburg

Leslie M.

HK$10,531 total

includes taxes & fees

28 Oct - 29 Oct

A modern kitchen with a central island, bar stools, a stainless steel refrigerator, and a backsplash with a geometric pattern.

8. Vineyard Vue - Wine Tastings Included

Healdsburg

Chris N.

HK$12,964 total

includes taxes & fees

3 Nov - 4 Nov

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Top Healdsburg Hotel Reviews

Calderwood Inn

10/10 Excellent

"Staff was wonderful. Thank you Kiki."

Dry Creek Inn MOD Collection by Sonesta

8/10 Good

"The temps were in the high 90's on the day I arrived. I got into my room at 7pm and the a/c was off and the room was a literal hotbox. It was extremely uncomfortable. I had to turn on the a/c and leave for a couple hours before considering going back. Upon returning it was only a little bit better and I was uncomfortable all night. I understand that a/c units are not just 'on' in every room, that would be beyond wasteful. But when someone is coming to your hotel when you know the windows are closed and the a/c unit is off, perhaps give them a room previously occupied the night before (at the very least), or have a staff member turn the a/c on when a guest is confirmed and expected. Besides that, everything was great. Quiet, clean, location, parking. Thank you"

Camellia Inn

10/10 Excellent

"Staff was excellent- stayed a few minutes late to be there to check us in after 4:30pm; helpful with recommendations for local wineries, etc. Nice to have afternoon wine (although we only took advantage upon arrival) and free tasting at the local Wilson wineries. Our room was outside the main building. It seemed not as well maintained/updated as those inside the main Inn. Overall, a very nice stay at the Camelia Inn. We would definitely stay again when back in the area."

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