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Healdsburg Vacation Rentals

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    Travelers to Healdsburg are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 20
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    5 of 5 bubbles (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3.5 of 5 bubbles (7) Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    This lovely little cottage is really a unique and hard to find category for a few guests or 2 couples. Furnished smartly, and priced right, this cottage offers big amenities for the vacation home traveler. Set on one acre, there is off street parking through gates, a hobby vineyard, and outdoor... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 bubbles Reviewed May 26, 2015
    Communication with owners was quick and easy. The place is close enough to town to walk. If you want to wake up and see vines, you won't be disappointed. Beads were super comfy...
    3 of 5 bubbles Reviewed June 10, 2013
    Yes, this cottage is comfortable and well furnished. Full kitchen, great hot tub, comfortable beds, lovely setting in a real vineyard. BUT: it is located off a fairly busy road...
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    1 / 6
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    4 bedroom, 3 bathroom, super modern 3000 square foot, 2 story bright big Chalk Hill Valley Home with family room, living room with fireplace, bright big kitchen, views, 2 bathrooms upstairs and 2 bedrooms upstairs, downstairs huge 500 sq foot studio included with big queen bed and views and quite... View all property information
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    Healdsburg, Sonoma County 95448
    1 / 33
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Terrace
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    About this property
    Drive down a tree-lined road. Vineyard is on left, beautiful gardens and bocce court in front, and garden area to the right in which to sit or stroll. Walk into a dramatic entry, and you'll see formal living room and dining rooms on the right, with a half bath across the hallway. To your left,... View all property information
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    Healdsburg, Sonoma County 95448
    1 / 13
    5 of 5 bubbles (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Cute, fully furnished, 3 bedroom/2 bath farm house in the city of Healdsburg. 10-15 minute walk/ 5 minute bike ride / 3 minute drive to Downtown Healdsburg. Few miles away from over 100 wineries! 30 DAY MINIMUM per Healdsburg Zoning Laws but we require longer stays based on seasonality THERE ARE... View all property information
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    Healdsburg, Sonoma County 95448
    1 / 20
    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Less than 15 min. to Healdsburg's Plaza Square, also within minutes to jumping off to the Russian River, bicycling, Old Town Windsor, and dozens of wineries! Gorgeous Craftsman home, remodeled, 4BR/3BA two story home with central HVAC, hardwood floors, formal living with TV/DVD, conversational... View all property information
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    Healdsburg, Sonoma County 95448
    1 / 37
    5 of 5 bubbles (3) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Inspired by the Villa Gallici in Aix-en-Provence, Villa Aix Vineyards combines traditional, French cottage warmth with fresh, contemporary farmhouse flair.Nestled on a serene 20-acre vineyard in the Alexander Valley appellation of Sonoma's gorgeous rolling hills, this private estate offers all the... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 bubbles Reviewed January 7, 2017
    We stayed at the Villa Aix Vineyards over New Year's. The villa is perfectly laid out for a party of twelve people (and one dog). The small vineyard is pleasant to walk in, and...
    5 of 5 bubbles Reviewed April 11, 2016
    We rented this house for my girlfriend's bachelorette weekend and it was absolutely beautiful! We were a large group but never left crowded as the house was very spacious, giving...
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    1 / 23
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Location Information
    Healdsburg, Sonoma County 95448
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    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Buena Vista is a Wine Country getaway on the Russian River with Spectacular Views just 5 Minutes from Healdsburg Plaza. When you reserve this 2400 square foot, 3 bedroom, 3 bath home, beautiful, panoramic views are just one of the many amenities you will be able to enjoy. The Buena Vista is an... View all property information
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    Healdsburg, Sonoma County 95448
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Spend your vacation in the heart of Healdsburg, CA at the Moorish-inspired Cypress House. Beautiful tiles, an interior courtyard, and an incredible view of downtown and beyond from the top floor terrace make this property unique to wine country. Located at the edge of a small shopping center, it... View all property information
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    Healdsburg, Sonoma County 95448
    1 / 22
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Private and in the country near the Dry Creek and Russian River Valleys and yet only 10 minutes to the Healdsburg Plaza Square. Main house is 3BR/3BA and cottage is studio and full bath with plenty of outdoor furniture. NOTE: Pool heated in high season only. Enter through private gate and wind up a... View all property information
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    Healdsburg, Sonoma County 95448
    1 / 30
    5 of 5 bubbles (10) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
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    About this property
    'Mona, a name given to house by our daughter when she could not say 'Sonoma,' is a four bedroom/four bath, completely remodeled home including a one bedroom/one bath guest house in the heart of Dry Creek Valley in Healdsburg, California. Our vacation home sits on one acre nestled among the vines... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 bubbles Reviewed September 13, 2015
    Mona was just as warm & welcoming as the photos showcased. Celebrating our Mother's 90th, it was the perfect location to enjoy time together as family- plenty of games to enjoy...
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    1 / 11
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Riverstone Ranch is truely a multi-family property. A location which caters to several generations with traditional main house, or modern 2BR/2BA "coup" or "Oak Tree House", each offers something a little different, all against gorgeous Russian River views and less than 5 minutes to downtown... View all property information
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    Healdsburg, Sonoma County 95448
    1 / 26
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our home is a perfect starting point to Alexander Valley and Dry Creek wineries and a short walk to the banks of Russian River where you can float, kayak, paddle board or just lay in the sun. Nested on Fitch Mountain, our home is in the heart of nature. You are close enough to downtown Healdsburg... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    5 of 5 bubbles Reviewed June 9, 2015
    I would definitely recommend this property. My wife and I stayed there with friends for a wine country holiday. The house seems recently remodeled with many seating areas both...
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    1 / 22
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Healdsburg, Sonoma County 95448
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Healdsburg, Sonoma County 95448
    1 / 37
    4.5 of 5 bubbles (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    All of the living at West Dry Creek View is at the back side of this beautiful modern minimalist country property. Three private acres offer a large in ground 22' x 60' swimming pool and large concrete hot tub amid gardens, emerald green lawn, and vineyard views galore, all less than ten minutes to... View all property information
    Location Information
    Healdsburg, Sonoma County 95448
    4 of 5 bubbles Reviewed March 15, 2015
    Beautiful location on west dry creek road making it convenient to get to many wineries and downtown Healdsburg but also secluded enough to get away from the hustle and bustle...
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    1 / 29
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Children's Pool
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    About this property
    Situated on 2.5 acres, just minutes from the quaint downtown of Windsor and about 10 minutes from the Healdsburg square, Woody Creek Retreat is at the pinnacle of convenience while offering the serenity of a quiet country luxury farmhouse. Ideal for families, couples, or friends wanting a to... View all property information
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    Healdsburg, Sonoma County 95492
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    1 / 23
    4 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Healdsburg, Sonoma County 95448
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Healdsburg, Sonoma County 95448
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Healdsburg, Sonoma County 95448
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Healdsburg, Sonoma County 95448
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Healdsburg, Sonoma County 95448
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Healdsburg, Sonoma County 95448
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Healdsburg, Sonoma County 95448
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Healdsburg, Sonoma County 95448
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Healdsburg, Sonoma County 95448
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Healdsburg, Sonoma County 95448
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Healdsburg, Sonoma County 95448
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    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Healdsburg, Sonoma County 95448
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Healdsburg, Sonoma County 95448
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Healdsburg, Sonoma County 95448
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    CHATTHAVELI is the perfect wine country retreat in Healdsburg, Sonoma County, California - close to Napa Valley, the Russian River, Guerneville, and the coast. Our home is walking distance from wineries, a 6-minute drive from downtown Healdsburg, a few short miles from hiking trails and kayaking,... View all property information
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    Healdsburg, Sonoma County 95448
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    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Healdsburg, Sonoma County 95448
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Healdsburg, Sonoma County 95448
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Healdsburg, Sonoma County 95448
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    Healdsburg, Sonoma County 95448
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Healdsburg, Sonoma County 95448
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Healdsburg, Sonoma County 95448
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    2nd floor: 11 foot ceilings. Beautiful, gourmet kitchen with stunning views. Kitchen is equipped with a Thermador 6 burner (and grill) gas stove top and double electric oven. Butcher block counter tops. Dishwasher, Professional quality knives and cookware. Large microwave. Spacious walk-in pantry.... View all property information
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    Healdsburg, Sonoma County 95448
    Healdsburg Flight and Weather Info
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    63° 39°
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    70° 42°
    May
    76° 45°
    June
    78° 46°
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    Healdsburg Vacation Rentals

    Beautiful Northern California has many fabulous destinations, and the town of Healdsburg in Sonoma County is at the top of the list. And if you are looking for a vacation rental in this slice of world famous wine country, we’ve got you covered. We have a huge variety of Healdsburg vacation rental listings. You might be looking for a large house for the whole family, or a quaint cottage for a special romantic getaway. Whatever your needs and budget, we can help you find the perfect vacation rental that will make your stay in Healdsburg even more amazing. We can also provide you with helpful user reviews of vacation rentals in Healdsburg and the surrounding area, so you’ll be sure to get good value for your money.

    Healdsburg a Slice of Paradise

    Small town charm, beautiful landscapes and outstanding weather are just a few of the trademark qualities that make Healdsburg so popular. Healdsburg combines five-star cuisine, rolling hills and world-acclaimed wine growing appellations for an experience you will never forget. When it’s time to relax at the end of the day, why stay in a cramped hotel when you can enjoy the comforts of home in one of our rental cottages, houses or cabins?

    Lots of Activities

    If you love the vibrant outdoors and colorful festivals, you will love Healdsburg. In April, you can help harvest roses and distill them into fragrant rose oil and rosewater as part of the Classic Perfume Rose Harvest & Distillation Tours. An annual sea food dinner at the Healdsburg Fire Department is also in April. From February to June, enjoy the "Russian River Good Old Days" exhibit at the Healdsburg Museum. And on the first Friday of the month, Williamson Wines sponsors an Epicurean Dinner at the Dry Creek Kitchen at Hotel Healdsburg.

    Food, Wine and Fun

    Speaking of eating, you won’t want to miss the chance to dine at Healdsburg’s amazing restaurants, including Affronti, Agave Mexican Restaurant &Tequila Bar, Thai Orchid Cuisine, Willi's Seafood & Raw Bar and Zin Restaurant & Wine Bar. And don’t forget to visit the beautiful wine country all around you, featuring names like Alexander Valley, Chalk Hill, Dry Creek Valley, and Russian River Valley. We’re here to help you make the most of your visit to Healdsburg. Let us help you find the perfect cozy cottage, cabin or house to make your stay in Healdsburg one you will always remember.