Search results; Over 1,000 homes in Healdsburg

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Guest favorite
Home in Healdsburg
Vineyard Vista, Modern Farmhouse Cottage with Pool
6 guests3 bedrooms4 beds2 baths
Jul 28 – Aug 2
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Jul 28 – Aug 2
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R72,700 ZAR for 5 nights

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Top guest favorite
Guesthouse in Healdsburg
Healdsburg Cottage-Workspace, Walk to Plaza
1 queen bed
Aug 10 – 15
R22,548 ZAR for 5 nights
4.94 out of 5 average rating, 342 reviews
Top guest favorite
Home in Healdsburg
Healdsburg Garden House
4 beds
Aug 10 – 15
R20,398 ZAR for 5 nights
4.93 out of 5 average rating, 599 reviews
Guest favorite
Guesthouse in Healdsburg
Healdsburg Contemporary Cottage With Lush Backyard Patio
1 queen bed
Aug 2 – 7
R42,609 ZAR for 5 nights
4.97 out of 5 average rating, 207 reviews
Guest favorite
Guesthouse in Healdsburg
The Roost - Sun Room
1 queen bed
Jul 26 – 31
R25,772 ZAR for 5 nights
4.94 out of 5 average rating, 336 reviews
Top guest favorite
Apartment in Healdsburg
Ultra-Modern 2 Bedroom Flat In Downtown Healdsburg
Free cancellation
Aug 24 – 29
R37,467 ZAR for 5 nights
4.98 out of 5 average rating, 107 reviews
Top guest favorite
Home in Healdsburg
Cuvée House
Free cancellation
Jul 27 – Aug 1
R50,574 ZAR for 5 nights
5.0 out of 5 average rating, 28 reviews
Top guest favorite
Home in Healdsburg
Healdsburg Downtown Charmer w/ Hot Tub!
Free cancellation
Sep 1 – 6
R55,168 ZAR for 5 nights
5.0 out of 5 average rating, 36 reviews
Top guest favorite
Home in Healdsburg
Riverhouse by the plaza
Free cancellation
Aug 16 – 21
R47,940 ZAR for 5 nights
5.0 out of 5 average rating, 30 reviews
Top guest favorite
Guest suite in Healdsburg
Bridle Path BNB - Private suite w/ hot tub & views
1 queen bed
Jul 28 – Aug 2
R22,390 ZAR for 5 nights
4.98 out of 5 average rating, 46 reviews
Top guest favorite
Home in Healdsburg
Dry Creek Valley Cottage
1 queen bed
Jul 19 – 24
R20,230 ZAR for 5 nights
4.95 out of 5 average rating, 465 reviews
Guest favorite
Apartment in Healdsburg
Downtown Healdsburg Perch
Free cancellation
Jul 29 – Aug 3
R52,154 ZAR for 5 nights
4.97 out of 5 average rating, 34 reviews
Guest favorite
Guesthouse in Healdsburg
Luxurious, Private, Healdsburg Guest Cottage
Free cancellation
Jul 27 – Aug 1
R39,722 ZAR for 5 nights
4.99 out of 5 average rating, 285 reviews
Guest favorite
Vacation home in Healdsburg
Downtown Healdsburg Hideaway
2 beds
Jul 19 – 24
R47,266 ZAR for 5 nights
4.97 out of 5 average rating, 62 reviews
Superhost
Room in Healdsburg
Stay with CynthiaBusiness owner,
Healdsburg Adventure Stay | Hot Tub + Views
Aug 3 – 8
R21,747 ZAR for 5 nights
New place to stay
Guest favorite
Guesthouse in Guerneville
Sweetwater Cottage
Free cancellation
Sep 8 – 13
R9,062 ZAR for 5 nights
4.95 out of 5 average rating, 245 reviews
Guest favorite
Villa in Healdsburg
Escape to Luxury: Healdsburg’s Hidden Gem Villa
Free cancellation
Sep 21 – 26
R123,800 ZAR for 5 nights
4.83 out of 5 average rating, 6 reviews
Superhost
Hotel room in Calistoga
A Room with a Brew: Stay at a Microbrewery in Napa
1 queen bed
Jul 21 – 26
R11,190 ZAR for 5 nights
4.74 out of 5 average rating, 964 reviews
Superhost
Room in Windsor
Stay with MarianneHosting for 9 years,
Rivermind, a Wine Country Retreat #2
Jul 20 – 25
R11,085 ZAR for 5 nights
4.91 out of 5 average rating, 109 reviews