We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals nearby Simi Winery

16275 Healdsburg Ave, Healdsburg, California 95448-9075
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    C$929 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    More filters
    Travellers to Healdsburg are booking April dates now. Secure your vacation rental today, and have the perfect trip.
    All 89 Rentals in Healdsburg
    VineHaven / Spa, Gardens, & Spectacular Vineyard Views1 / 21
    (5)Excellent
    3.3 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Spectacular Two-Story Tuscan Villa Estate Home w/ Spa, Decks & Views1 / 32
    (16)Very good
    3.3 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    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
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    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
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 16, 2016
    the house is fabulous and the location is perfect.minutes to town and lots of wineriespeaceful setting and cool clean house
    See all reviews
    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,...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    4.1 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Hot Tub
    • Balcony
    • Washer
    • Internet Access
    • Cable/satellite TV
    • 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...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Grill
    • Patio
    • Washer
    • Housekeeping Included
    • Central Heating
    • Mountain Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    See all reviews
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3.3 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Mountain Views
    • Patio
    • Cable/satellite TV
    • Grill
    • Central Heating
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 and life jackets....
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Big Oak Vineyard / Vineyard Views, 3br/2ba, w.Spa and Attached to a Winery!1 / 23
    (4)Excellent
    2.0 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Parking
    • Washer
    • DVD Player
    • Internet Access
    • Grill
    • Air Conditioning
    • Patio
    Suitability
    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...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3.4 kilometres from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Housekeeping Included
    • Waterfront
    • Washer
    • Mountain Views
    • Patio
    • Cable/satellite TV
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 well maintained 2...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    2.9 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Internet Access
    • Secure Parking
    • Cable/satellite TV
    • 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...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Save time - get the best Healdsburg rentals sent straight to your email!
    Get the List
    5.4 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Washer
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * TurnKey photo-verifies this home is professionally cleaned with products approved by the EPA for use against COVID-19. * 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...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Rendezvous Under the Oaks / Vineyard Home w. Pool, Spa, and Basketball Court1 / 21
    (1)Terrible
    1.8 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • Parking
    • Hot Tub
    • Grill
    • Internet Access
    Suitability
    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...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    1.5 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Washer
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Grill
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Everything for your stay has been designed to provide you with an experience you'll remember for years to come. Our concierge team and in-house sommelier are happy to assist you with planning your next vacation. We can help with scheduling private wine tastings, guided hikes, hot air balloon rides,...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    3.4 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Patio
    • Grill
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find your bliss amid the vineyards in Healdsburg Wine Country. This bright, airy, and immaculate home offers everything you want: first-rate entertainment system, super comfortable bedrooms — even a picnic basket and your own bottle of wine from the grapes that surround you! It offers plenty of...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1.2 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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 8 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...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3.5 kilometres from Simi Winery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    2.7 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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. Located in a garden setting 5 blocks from the Healdsburg Plaza in the central, historic district, it is adjacent to a 2-story, 1880's...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    1.6 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Parking
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    7.1 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    • Parking
    • Patio
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Russian River Wine Regions. The home is just Five minutes from the Healdsburg Plaza Square with dozens of Winery Tasting Rooms, Award...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    2.9 kilometres from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Grill
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Charming 2 bedroom 1880's Cottage is the perfect wine country getaway for 4. Just 2 blocks from the historic Downtown Plaza, Restaurants, Boutiques and Wine Tasting. The newly remodeled contemporary furnished interior is well appointed for you getaway needs. Living Loom, Dining area, Kitchen...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    List your property for free!
    List your holiday rental where Tripadvisor travellers can find it.
    Add a Listing
    0.4 kilometres from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Sauna
    • Washer
    • DVD Player
    • Grill
    • 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...
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
    2.2 kilometres from Simi Winery
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Hot Tub
    • Grill
    • Wi-Fi
    • Terrace
    • Secure Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    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...
    View all property information
    Location Information
    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
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Central Heating
    • Balcony
    • Mountain Views
    • Grill
    • DVD Player
    • 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....
    View all property information
    Location Information
    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
    (47)Excellent
    2.9 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Washer
    • DVD Player
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Crossroads Vineyard:  In the Heart of Healdsburg Wine Country1 / 23
    (88)Excellent
    2.6 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Patio
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    0.9 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Hot Tub
    • Patio
    • Parking
    • Washer
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Spectacular view of Dry Creek Valley1 / 26
    (1)Excellent
    1.7 kilometres from Simi Winery
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Parking
    • Internet Access
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    8.2 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Washer
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    • Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    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 / 44
    (57)Very good
    4.3 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Central Heating
    • Washer
    • Patio
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Enchanting Wine Country Villa1 / 24
    (3)Excellent
    8.7 kilometres from Simi Winery
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Hot Tub
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Bunkhouse at Side Road Farm charming one bedroom cottage1 / 35
    (17)Excellent
    7.1 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Secluded Luxury Vineyard Estate House and Guest House1 / 50
    (73)Excellent
    8.5 kilometres from Simi Winery
    5 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Parking
    • Terrace
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Washer
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 4
    Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!1 / 14
    (70)Excellent
    5.7 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    13.2 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Washer
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Beautiful Studio Getaway  in the Heart of Wine Country1 / 12
    (36)Excellent
    5.9 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    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
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Parking
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    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 / 47
    (16)Excellent
    6.4 kilometres from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Washer
    • Internet Access
    • Housekeeping Included
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    5.6 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Patio
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    2.8 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Parking
    • Internet Access
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Enjoy the Sunset from Upscale Home Among Vineyards — short walk to Healdsburg1 / 48
    (55)Excellent
    3.4 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Parking
    • Air Conditioning
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Stunning Mountain Top Estate with View Over Dry Creek Vineyards1 / 28
    (19)Excellent
    8.6 kilometres from Simi Winery
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Dry Creek Cottage - Healdsburg1 / 6
    (48)Excellent
    1.5 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Patio
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    1.5 kilometres from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Terrace
    • Parking
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Balcony
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    The Cabin on Fitch Mountain1 / 37
    (6)Very good
    4.3 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Internet Access
    • Patio
    • Parking
    • Terrace
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Tanda Tula, Wine Country Sanctuary1 / 28
    (81)Excellent
    7.0 kilometres from Simi Winery
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Washer
    • Internet Access
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Creek Front Vineyard, West Dry Creek Healdsburg CA1 / 30
    (10)Excellent
    6.9 kilometres from Simi Winery
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Washer
    • Internet Access
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    Wine country getaway; stay in a winery1 / 12
    (10)Excellent
    3.4 kilometres from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Updated cabin, right on Russian River, amazing views & location!1 / 23
    (14)Excellent
    4.5 kilometres from Simi Winery
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Parking
    • DVD Player
    • Internet Access
    • Washer
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Downtown Healdsburg Loft - (30 day minimum rentals only)1 / 19
    (1)Excellent
    2.4 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Internet Access
    • Terrace
    • Cable/satellite TV
    • Washer
    • Patio
    • Parking
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Mountain Cottage near Russian River, hiking and downtown, family and pet friendl1 / 27
    (5)Very good
    3.2 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    homeaway logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Patio
    • Washer
    • Parking
    • Central Heating
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1
    List your property
    Owner log in
    $CAD
    Canada (English)
    © 2020 TripAdvisor LLC All rights reserved.

    This is the version of our website addressed to speakers of English in Canada. If you are a resident of another country or region, please select the appropriate version of Tripadvisor for your country or region in the drop-down menu.