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Holiday Rentals near Simi Winery

16275 Healdsburg Ave, Healdsburg, California 95448-9075
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    Travellers to Healdsburg are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    All 90 Rentals in Healdsburg
    3.9 miles from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    2.7 miles from Simi Winery
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Stunning NEW Modern Farmhouse, Just 3 Blocks from Healdsburg Plaza1 / 27
    (5)Excellent
    2.2 miles from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    4 bedroom home at the gateway to Alexander Valley.1 / 41
    (3)Very good
    1.0 miles from Simi Winery
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
    1.3 miles from Simi Winery
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Hot Tub
    • Grill
    • Wi-Fi
    • Terrace
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    Pet friendly
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    About this property
    The Residence at Comstock Wines is located on our 17 acre Estate Vineyards and was completed in 2016. The Residence boasts four stunning Master Suites, each offering private entrance, vineyard view terrace, gas fireplace, OrganicPedic beds, 1500 thread count linens, shower with vineyard view window...
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
    1.7 miles from Simi Winery
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Central Heating
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    • Mountain Views
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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....
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 6 Bathrooms, Sleeps 8
    Beautiful Views!  Dry Creek Valley Retreat with Deck & Pool, 5 min to Healdsburg1 / 46
    (65)Excellent
    1.8 miles from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    4.0 miles from Simi Winery
    3 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 10
    Enjoy a Slice Of Country--Two miles to Downtown Healdsburg - Pets Welcome1 / 35
    (40)Excellent
    0.8 miles from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Breathtaking Dry Creek Estate - Modern, Spacious, Luxury!1 / 33
    (5)Excellent
    1.5 miles from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Spectacular view of Dry Creek Valley1 / 24
    (1)Excellent
    1.1 miles from Simi Winery
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Dry Creek Valley Home and Vineyard1 / 24
    (39)Excellent
    2.1 miles from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Superb Healdsburg Location, Spectacular Views, Minutes to Town1 / 49
    (39)Excellent
    5.1 miles from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Pet Friendly Wine Country Getaway On The Russian River Just 5 Minutes From Town1 / 39
    (65)Very good
    2.7 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Enchanting Wine Country Villa1 / 36
    (8)Excellent
    5.4 miles from Simi Winery
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Bunkhouse at Side Road Farm charming one bedroom cottage1 / 34
    (29)Excellent
    4.4 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!1 / 14
    (82)Excellent
    3.5 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Beautiful Studio Getaway  in the Heart of Wine Country1 / 12
    (64)Excellent
    3.6 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Vineyard Guest House1 / 31
    (17)Excellent
    4.6 miles from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    4,700 ft 4 bed & 4 bath ranch, 120 acres all to yourself with a lake and farm.1 / 50
    (22)Excellent
    4.0 miles from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    • Housekeeping Included
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    luxuriously appointed new large guest suite in a landmark Victorian1 / 21
    (49)Excellent
    3.4 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1.7 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Dry Creek Cottage - Healdsburg1 / 6
    (86)Excellent
    0.9 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    The Cabin on Fitch Mountain1 / 37
    (35)Very good
    2.7 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Tanda Tula, Wine Country Sanctuary1 / 28
    (104)Excellent
    4.3 miles from Simi Winery
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Creek Front Vineyard, West Dry Creek Healdsburg CA1 / 30
    (27)Excellent
    4.3 miles from Simi Winery
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    Wine country getaway; stay in a winery1 / 12
    (17)Excellent
    2.1 miles from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Private 3 Bed + Cottage Wine Country Estate With Pool And More1 / 23
    (34)Excellent
    3.4 miles from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Updated cabin, right on Russian River, amazing views & location!1 / 24
    (31)Excellent
    2.8 miles from Simi Winery
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Downtown Healdsburg Loft - (30 day minimum rentals only)1 / 19
    (4)Excellent
    1.5 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Mountain Cottage near Russian River, hiking and downtown, family and pet friendl1 / 27
    (24)Very good
    2.0 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Luxury Wine Country Home in the Heart of Healdsburg with a Private Pool.1 / 50
    (31)Excellent
    2.2 miles from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    A redwood retreat in the heart of Sonoma County wine country.1 / 50
    (15)Very good
    3.5 miles from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Healdsburg Bliss House-Sonoma Wine Country Sweeping Panoramic Vineyard Views1 / 14
    (147)Excellent
    2.4 miles from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Healdsburg River Front Oasis Retreat.1 / 28
    (94)Excellent
    2.6 miles from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Morning Dew- A Riverfront Healdsburg Home1 / 34
    (23)Very good
    2.7 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Newly Listed 4BR/4.5BA Gorgeous 17 Acre Estate/Pool/Hot Tub/5 mins - Hburg Plaza1 / 34
    (22)Excellent
    3.3 miles from Simi Winery
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    1.9 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Downtown Healdsburg Victorian Cottage: recently remodeled, one story, open floor plan, chefs kitchen, indoor-outdoor living, covered porch, and hot tub. Easy walk to Plaza, restaurants, wine tasting lounges, movies, performing arts theater, art galleries, and boutique shops. At the Center of Dry...
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Hilltop Hideaway:  Bright, Fresh, Modern, Views And Only 2 Miles To Plaza1 / 45
    (122)Excellent
    2.7 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Dry Creek Farm--Vineyard, Pool and Spa with Stunning View, Dog friendly1 / 50
    (110)Excellent
    4.2 miles from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1.4 miles from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Beautiful Mountain Top retreat less than 10 mins from downtown Healdsburg!1 / 42
    (90)Excellent
    2.4 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)1 / 29
    (27)Very good
    5.8 miles from Simi Winery
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Close to Plaza/15 Acre Estate/swiming Pool and Bocce Ball1 / 48
    (84)Excellent
    3.9 miles from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Healdsburg Cottage  Walk to the Plaza, Workspace1 / 37
    (148)Excellent
    1.7 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Modern Luxury Farm House in the Heart of Dry Creek Valley1 / 47
    (12)Excellent
    5.6 miles from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    4.1 miles from Simi Winery
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Sauna
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    6.4 miles from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Cabin In An Old Vine Zinfandel Vineyard. Dry Creek Valley. Five Miles To Plaza.1 / 11
    (200)Excellent
    2.4 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Dog Friendly  Vineyard Estate Cottage with Lap Pool and Incredible Views1 / 18
    (46)Excellent
    5.2 miles from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Outdoor Pool (Unheated)
    • Balcony
    • Central Heating
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    • Internet Access
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    Pet friendly
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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