Healdsburg: Vacation Rental By Owner

Showing 20 Of 97 Vacation Rentals
  • Property-1 Image 1
    Cabin Select Dates for Price
    • 2 Bed
    • 2 Baths
    • (3) Very Good
    Healdsburg, CA

    You've discovered a 'Wine Country' gem! Unique and affordable. A wine country cabin with lots of charm. 1 Block walk to the Russian River and Camp Rose beach. 5... ...more

  • Property-2 Image 1
    Cottage $239 / Nightly
    • 1 Bed
    • 1 Baths
    • (107) Wonderful
    Healdsburg, CA

    The cottage is a well-appointed, stand-alone unit with a private gate and entrance which provides an ideal retreat for touring the Sonoma and Napa wine country.... ...more

  • Property-3 Image 1
    House $744 / Nightly
    • 3 Bed
    • 3 Baths
    • (48)
    Healdsburg, CA

    This home is fully furnished with quality furniture, comfortable newer beds and all living amenities that you could need included. It is river-front on a double... ...more

  • Property-4 Image 1
    Chateau / Country House Select Dates for Price
    • 4 Bed
    • 3 Baths
    • (88) Wonderful
    Healdsburg, CA

    After a day of visiting the surrounding wineries, biking on the beautiful trails, canoeing on the Russian River, dining in Healdsburg’s famous bistros and... ...more

  • Property-5 Image 1
    Cottage $309 / Nightly
    • 2 Bed
    • 1 Baths
    • (36)
    Healdsburg, CA

    THIS COTTAGE IS A TRUE RETREAT. Our cottage is one of the best priced homes on the river with scenic views and a large spa. It is truly a different experience to... ...more

  • Property-6 Image 1
    House $1,033 / Nightly
    • 4 Bed
    • 4 Baths
    • (63)
    Healdsburg, CA

    'Mona, a name given to the house by our daughter when she could not say 'Sonoma,' is a four bedroom/four bath home. The property includes a one bedroom/one bath... ...more

  • Property-7 Image 1
    House $1,029 / Nightly
    • 4 Bed
    • 4 Baths
    • (59) Wonderful
    Healdsburg, CA

    Mill Creek Estate is an exceptional Vineyard Estate located in the heart of the Sonoma Wine Country near the quaint town of Healdsburg and less than 6 minutes... ...more

  • Property-8 Image 1
    Estate $1,867 / Nightly
    • 5 Bed
    • 3 Baths
    • (18) Excellent
    Healdsburg, CA

    Set in the hills above Dry Creek Valley, this house is a glass and steel house made with prefabricated materials that sits on 80 acres.  Featured on the cover of... ...more

  • Property-9 Image 1
    House $530 / Nightly
    • 3 Bed
    • 2 Baths
    • (65) Excellent
    Healdsburg, CA

    RATES Rates are $395/night for up to FOUR guests. Each additional guest is $25/night. Max 8 guests. For calculating rates, a "guest" is a person over the age of... ...more

  • Property-10 Image 1
    Villa $1,112 / Nightly
    • 4 Bed
    • 5 Baths
    • (17) Wonderful
    Healdsburg, CA

    This Elegant Villa offers World Class Views, High End Appointments, a Chef Inspired Kitchen, Indoor and Outdoor Dining and Entertainment Areas. The property is... ...more

  • Property-11 Image 1
    Cabin Select Dates for Price
    • 2 Bed
    • 3 Baths
    • (10) Wonderful
    Healdsburg, CA

    Escape to wine, water, nature, and cozy cabin comfort that's a short trip from San Francisco (1hr 15 min) and only minutes to charming downtown Healdsburg and Dry... ...more

  • Property-12 Image 1
    Cottage Select Dates for Price
    • 1 Bed
    • 1 Baths
    • (37) Exceptional
    Healdsburg, CA

    Luxurious 500sft Contemporary Cottage with French Doors opening onto the landscaped garden with sitting area, Kitchenette, sky-lighted stone shower, Living Room&... ...more

  • Property-13 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (56) Wonderful
    Healdsburg, CA

    **********Please send inquiries instead of booking requests. My screening and contract process requires longer than the 24 hours allotted to the booking request.... ...more

  • Property-14 Image 1
    House $745 / Nightly
    • 4 Bed
    • 3 Baths
    • (47)
    Healdsburg, CA

    Thank you for considering Heaven in the Redwoods. We are so excited to share this property as owners. Our property is a cottage-style home featuring 4 bedrooms... ...more

  • Property-15 Image 1
    Chateau / Country House $1,307 / Nightly
    • 4 Bed
    • 4 Baths
    Healdsburg, CA

    Xanadu Healdsburg Luxury Vacation home in Healdsburg. In the Heart of Sonoma County Wine Country, Healdsburg is the hub of the Dry Creek, Alexander Valley and... ...more

  • Property-16 Image 1
    House $380 / Nightly
    • 2 Bed
    • 2 Baths
    • (136)
    Wooded Restful Retreat, with broad... Healdsburg, CA

    This is a perfect spot for up to four adults who seek a restorative, restful experience of being pampered by nature, night skies, and a chance to be away in a... ...more

  • Property-17 Image 1
    House $449 / Nightly
    • 3 Bed
    • 2 Baths
    • (24)
    Healdsburg, CA

    Beautifully located, perched just above the Russian River, on S. Fitch Mountain, this vintage 1927 river home has been beautifully renovated and modernized with... ...more

  • Property-18 Image 1
    House $669 / Nightly
    • 3 Bed
    • 2 Baths
    • (37)
    Healdsburg, CA

    Very well located at the north end of Healdsburg and the beginning of the famed Dry Creek Valley and vineyards, this newly renovated 50’s charmer is a lovely,... ...more

  • Property-19 Image 1
    House $1,090 / Nightly
    • 3 Bed
    • 3 Baths
    • (25) Wonderful
    Healdsburg, CA

    Location, location location! Perfectly situated only 3 miles (a 5-7 minute drive) from the charming and historic Healdsburg Plaza, this fabulous, custom... ...more

  • Property-20 Image 1
    House $1,431 / Nightly
    • 5 Bed
    • 5 Baths
    • (21) Excellent
    Healdsburg, CA

    Nestled on 10 acres in the prestigious Chalk Hill appellation of the Alexander Valley, this rustic, beautifully renovated and newly furnished, 5br/4.5ba, 3200 sq.... ...more

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Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Healdsburg. Many accommodations in Healdsburg provide "Non Smoking Only", there are 107, or there are 85 of Vacation Rentals in Healdsburg with a "Biking", there are also 82 with "Hiking", which is another great reason to visit Healdsburg.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Healdsburg. The most expensive month of the next 12 months is in July, where prices hit an average of $376 a night. In June, prices will hit an average low of $883 per night.