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$4,084 total

includes taxes & fees

8 Oct - 9 Oct

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

Northwest Santa Rosa

kevin c.

HK$2,894 total

includes taxes & fees

4 Nov - 5 Nov

A wooden interior with a dining area, a bench, and a mirror on the wall.

3. Cozy Riverfront Cabin - Beach Access & Wood Stove

Guerneville

Jehanne H.

HK$4,374 total

includes taxes & fees

8 Oct - 9 Oct

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

4. Wildflower

Windsor

Keri S.

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

5. Wine Country Cottage Escape

Fulton

Tina A.

HK$2,892 total

includes taxes & fees

20 Oct - 21 Oct

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

6. Russian River Retreat: Private Beach & DogFriendly

Forestville

Anna K.

HK$5,236 total

includes taxes & fees

11 Oct - 12 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$10,710 total

includes taxes & fees

14 Oct - 15 Oct

A covered patio with a dining table, chairs, and a sofa.

8. Redwood Riverfront - Hot Tub and Tastings Included

Healdsburg

Tessa W.

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Top Healdsburg Hotel Reviews

The Lodge at Healdsburg, Tapestry Collection by Hilton

10/10 Excellent

"The hotel was beautiful. There were outside areas for gathering with fireplaces. Pool and hot tub were great. Nice ambiance!"

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!"

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