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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 September dates now. Secure your holiday rental today, and have the perfect trip.
    All 32 Rentals in Healdsburg
    Spectacular Two-Story Tuscan Villa Estate Home w/ Spa, Decks & Views1 / 32
    (15)Very good
    3.3 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    VineHaven / Spa, Gardens, & Spectacular Vineyard Views1 / 21
    (5)Excellent
    3.3 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Maison du Soleil / Stunning One-Story 4br/3ba home w.Spa, and Ping Pong Table!1 / 25
    (5)Excellent
    1.7 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    West Dry Creek View1 / 37
    (4)Very good
    6.9 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 March 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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    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...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Limerick Lane / Stunning, Quiet, Contemporary, Single-Level, Eco-Friendly1 / 25
    (3)Excellent
    7.0 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Grill
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    • Private Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 October 2016
    the house is fabulous and the location is perfect.minutes to town and lots of wineriespeaceful setting and cool clean house
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    About this property
    Location, location location! Perfectly situated only 3 miles (a 5-7 minute drive) from the charming and historic Healdsburg Plaza, this fabulous, custom three-bedroom home abounds with special eco-friendly features. You will be wowed by this modern home’s beautiful open-beamed cathedral ceiling,...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6.3 kilometres from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Upscale, Modern four bedroom, three bath home1 / 20
    (5)Very good
    7.6 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2016
    I rented this house with a group of 7 and it was PERFECT! The property is secluded, the pool is amazing and the beds are comfortable. The location is removed from Santa Rosa...
    Reviewed 11 September 2014
    I was staying at Bella Gia with my husband and a few friends. We were in Healdsburg for our friends' wedding. The house is in an extremely convenient location to downtown...
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    About this property
    Enjoy the best of two worlds, the peace and tranquility of ‘country living’ among the vineyards and wineries of the Russian River Valley, and the convenience of being only five minutes from the historic Healdsburg’s Plaza. Bella Terra Healdsburg is an upscale, and modern appointed four bedroom,...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4.4 kilometres from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Grill
    • Washer
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dry Creek Retreat Discover the luxuries of wine country living at Dry Creek Retreat, an exquisite 55-acre vineyard, 5,000-case state-of-the-art winery, and luxury home in the rolling hills of Healdsburg. Not only does this vineyard make world-class wines, it offers access to a gorgeous private...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3.3 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Washer
    • Grill
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    • Mountain Views
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RIVER VIEW LODGE River View Lodge appeals to guests with its spectacular riverfront setting, spacious river view deck, charming décor, exceptionally comfortable beds and linens, outstanding cleanliness, and quality amenities. River View features private river access, and includes kayaks, paddles...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beautiful mountain top wine retreat in Healdsburg!1 / 26
    (1)Excellent
    3.9 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Grill
    • Patio
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    • Housekeeping Included
    • Central Heating
    • Mountain Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 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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    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...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Big Oak Vineyard / Vineyard Views, 3br/2ba, w.Spa and Attached to a Winery!1 / 25
    (4)Excellent
    2.0 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Parking
    • Washer
    • DVD Player
    • Internet Access
    • Grill
    • Air Conditioning
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shaded by a 100-year-old oak tree, this very special home ‘lives’ on 30 vineyard acres and is off Dry Creek Road, just one mile west of the north end of charming, upscale, historic, Healdsburg in the heart of Sonoma County’s Wine Country. Newly renovated, this 3 bedroom/2 bath, Ranch House with...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4.1 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Balcony
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully located, perched just above the Russian River, on S. Fitch Mountain, this vintage 1927 river home has been beautifully renovated and modernized with central heat/AC, new dual-paned windows, high open-beamed ceilings, and all the modern conveniences while still maintaining its vintage...
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.9 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Washer
    • DVD Player
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4.5 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Housekeeping Included
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Buena Vista is a Wine Country getaway on the Russian River with Spectacular Views just a short drive 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...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Alexander Valley Retreat / Private, Country, Views and only 3 miles to town!1 / 23
    (1)Excellent
    3.3 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Air Conditioning
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    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is located in northeast Healdsburg on Alexander Valley Road, at the mouth of the Alexander Valley and just minutes from the Dry Creek Valley. This beautiful, 2-story 2,400 sqft home is well-maintained, with mature English garden style landscaping, flagstone walkways and back patio, fruit...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3.4 kilometres from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Housekeeping Included
    • Waterfront
    • Patio
    • Mountain Views
    • Grill
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    REDWOOD RIVER HOUSE Cozy Riverfront Home with Peace and Seclusion awaits you in the heart of Healdsburg. Tucked into one of the best locations on Healdsburg's Riverfront awaits this upscale cottage. Open Floor Plan with lots of Natural Light and Large Expansive Deck. Redwood River House is a...
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4.4 kilometres from Simi Winery
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    1.8 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Parking
    • Hot Tub
    • Grill
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning gated modern ranch house is nestled on one acre among the vineyards, and very well located at the north end of Healdsburg on Alexander Valley Road. Just remodeled, professionally decorated and furnished, this single story, 2000 sq. ft., 3 bedroom, 2.5 bath home sits under the shade of...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3.2 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    Visit our stunning new home for an ultimate wine country experience. It is your base camp for your wine tasting journey. Walk to world class wineries or ride your bike along the rows of vines. Waltz through our vineyard and picnic under an olive tree - while taking in the amazing views. The home...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.3 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to heavenly Healdsburg and Hilltop's Vista Villa! This gated 2-bedroom, 2-bath luxury Tuscan inspired villa is located only 3 miles from the historic Healdsburg plaza on one hillside acre near the top of the east side of Fitch mountain and is the only home this close to the top! This...
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Healdsburg Contemporary Cottage1 / 8
    (1)Excellent
    2.9 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Internet Access
    • Balcony
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    • Terrace
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2017
    This was the best money I have ever spent on a vacation property. Where do I start? This quaint, tastefully decorated cottage is perfectly located. It is close enough to the...
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    About this property
    The Space The perfect home away from home. Makes this your personal sanctuary wether you are staying for the weekend or for the whole month while looking for the perfect home to buy. Well appointed, decorated with international contemporary art with just enough touches that take you beyond the...
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Wine Country Cottage1 / 14
    (7)Average
    3.6 kilometres from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
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    • Mountain Views
    • Cable/satellite TV
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 May 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...
    Reviewed 11 June 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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    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...
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5.4 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Washer
    • Air Conditioning
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW A lavish retreat for the ultimate group getaway, this stunning 3BR/3BA home with a guest suite is hedged by expansive vineyards and mature trees. Spend an easy afternoon lounging poolside or relaxing in the hot tub. Then enjoy an evening gathered around the fire pit telling...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1.2 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly remodeled vacation rental home is wonderfully located less than 10 minutes north of downtown Healdsburg. It is nestled on the rolling hills of Dry Creek Valley with views looking towards Alexander Valley. Recently refreshed with stylish furnishings, fixtures and lighting system, the home...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    • Grill
    • Wi-Fi
    • Terrace
    • Secure Parking
    • Air Conditioning
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    0.4 kilometres from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Sauna
    • Washer
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    • Mountain Views
    • Hot Tub
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello wonderful Guests! We are happy to share our beautiful home that we have built from scratch 8 years ago. We have put much thought and consideration into each aspect of the home. We have children, so we have made this home very family friendly. Children simply love the home and grounds with...
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    3.1 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2.8 kilometres from Simi Winery
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
    • Central Heating
    • Balcony
    • Mountain Views
    • Grill
    • DVD Player
    • Porch
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    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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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 6 Bathrooms, Sleeps 8
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    7.3 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Armida Vineyards Cottage Enjoy the beauty of Healdsburg from the middle of a 12-acre vineyard at this three-bedroom vacation cottage, where you'll have your very own scenic deck and enclosed yard! Gorgeously situated just three miles from central Healdsburg in the heart of California wine...
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    Windsor, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5.5 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Getaway on Dry Creek Experience the best of California wine country at this two-bedroom Healdsburg home, where you'll enjoy a private outdoor hot tub, two patios and a deck, and an ideal location close to restaurants and tasting rooms. This dog-friendly retreat sits on a tree-lined property...
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    Geyserville, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.5 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning vineyard estate home is perched on a hill with spectacular 360-degree vineyard views of Geyser Peak, Alexander Valley and the Dry Creek hills. This spacious home features a lovely pool & spa, gourmet kitchen, wrap-around veranda, vaulted ceilings with crown moldings, hardwood...
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    Location Information
    Geyserville, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5.3 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Grill
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in scenic Alexander Valley next door to Starlite Vineyards, this 3-bedroom, 2-bath historic home boasts views of vineyards rife with Cabernet, Zinfandel and Viognier, plenty of space and lots of comfort. A complimentary tasting and private tour at Starlite Vineyards comes with every stay!...
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    Location Information
    Geyserville, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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