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Vacation Rentals nearby Simi Winery

16275 Healdsburg Ave, Healdsburg, California 95448-9075
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    Travellers to Healdsburg are booking November dates now. Secure your vacation rental today, and have the perfect trip.
    All 144 Rentals in Healdsburg
    4.4 kilometres 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 / 28
    (6)Excellent
    3.5 kilometres 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
    (6)Excellent
    1.6 kilometres from Simi Winery
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    2.2 kilometres from Simi Winery
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Hot Tub
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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
    2.8 kilometres 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
    • Grill
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    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    (66)Excellent
    2.9 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    6.4 kilometres from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
    Enjoy a Slice Of Country--Two miles to Downtown Healdsburg1 / 35
    (41)Excellent
    1.3 kilometres 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 / 36
    (5)Excellent
    2.5 kilometres 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
    Superb Healdsburg Location, Spectacular Views, Minutes to Town1 / 48
    (40)Excellent
    8.2 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    Pet Friendly Wine Country Getaway On The Russian River Just 5 Minutes From Town1 / 29
    (65)Very good
    4.3 kilometres 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
    Bunkhouse at Side Road Farm charming one bedroom cottage1 / 29
    (31)Excellent
    7.1 kilometres from Simi Winery
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 1
    Secluded Luxury Vineyard Estate Guest House1 / 17
    (85)Excellent
    8.5 kilometres 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
    NewTree Ranch Estate Retreat, Eco-Luxury Farm Stay 4.7 miles to Healdsburg1 / 51
    (22)Excellent
    6.4 kilometres from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    2.8 kilometres 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 / 9
    (97)Excellent
    1.5 kilometres 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
    Creek Front Vineyard, West Dry Creek Healdsburg CA1 / 30
    (31)Excellent
    6.9 kilometres from Simi Winery
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Patio
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    Healdsburg, Sonoma County
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    Private 3 Bed + Cottage Wine Country Estate With Pool And More1 / 23
    (34)Excellent
    5.5 kilometres from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Sauna
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Wine country getaway; stay in a winery1 / 12
    (17)Excellent
    3.4 kilometres 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
    Updated cabin, right on Russian River, amazing river access & location!1 / 24
    (38)Excellent
    4.5 kilometres 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
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    Downtown Healdsburg Loft - (30 day minimum rentals only)1 / 18
    (4)Excellent
    2.5 kilometres from Simi Winery
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Healdsburg, Sonoma County
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
    Luxury Wine Country Home in the Heart of Healdsburg with a Private Pool.1 / 50
    (31)Excellent
    3.6 kilometres from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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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 (w/ Fiber Internet)1 / 29
    (17)Very good
    5.7 kilometres from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
    Spectacular view of Dry Creek Valley1 / 24
    (1)Excellent
    1.7 kilometres 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
    (41)Excellent
    3.5 kilometres 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
    Entire Resort Villa *pool-spa-tennis-wine-dine*1 / 36
    (8)Excellent
    8.7 kilometres 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
    Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!1 / 14
    (82)Excellent
    5.7 kilometres 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
    (71)Excellent
    5.9 kilometres 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
    7.5 kilometres 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
    luxuriously appointed new large guest suite in a landmark Victorian1 / 19
    (56)Excellent
    5.6 kilometres 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
    The Cabin on Fitch Mountain1 / 37
    (40)Very good
    4.3 kilometres 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
    7.0 kilometres from Simi Winery
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    Healdsburg Bliss House-Sonoma Wine Country Sweeping Panoramic Vineyard Views1 / 14
    (155)Excellent
    3.8 kilometres 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 / 27
    (101)Excellent
    4.3 kilometres 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 / 35
    (26)Very good
    4.4 kilometres 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 5BR/5.5BA Gorgeous 17 Acre Estate/Pool/Hot Tub/5 mins - Hburg Plaza1 / 29
    (23)Excellent
    5.3 kilometres 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
    3.1 kilometres 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
    8.6 kilometres from Simi Winery
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Whispering Oaks Estate--Stunning Dry Creek Valley Estate with Views1 / 34
    (25)Very good
    8.7 kilometres from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    3.5 kilometres 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
    Stay surrounded by Fitch Mountain Park and Open Space Preserve.1 / 14
    (8)Very good
    4.5 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful Mountain Top retreat less than 10 mins from downtown Healdsburg!1 / 39
    (93)Excellent
    3.9 kilometres 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
    Santini Farmhouse--Luxury Cottage in the Center of Dry Creek Valley1 / 46
    (14)Excellent
    9.0 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Westside Vista  Wine Country Guest House1 / 23
    (2)Excellent
    10.3 kilometres 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
    Dog Friendly Healdsburg Vineyard Estate Cottage with Lap Pool/Incredible Views1 / 18
    (46)Excellent
    8.4 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Outdoor Pool (Unheated)
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Private Vineyard Haven1 / 44
    (13)Excellent
    3.4 kilometres 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
    Views, Hot Tub, Fireplace, Semi-Private Beach Close By , Pet-Friendly1 / 16
    (122)Very good
    4.5 kilometres 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
    Modern country cottage: swimming pool, privacy, vineyard & 5 min. to Healdsburg1 / 47
    (165)Very good
    8.3 kilometres 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
    4.0 kilometres from Simi Winery
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Grill
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    10.4 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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