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Healdsburg Holiday Rentals

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    Travellers to Healdsburg are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 26 Rentals in Healdsburg
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    Pristine Chalk Hill valley bright big studio!1 / 17
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Charming Apartment in Dry Creek Valley, Healdsburg1 / 20
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Zinscape1 / 30
    (18)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Studio, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Private Garden
    • Parking
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Less than 15 min. to Healdsburg's Plaza Square, also within minutes to jumping off to the Russian River, bicycling, Old Town Windsor, and dozens of wineries! Gorgeous Craftsman home, remodeled, 4BR/3BA two story home with central HVAC, hardwood floors, formal living with TV/DVD, conversational...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bathrooms, Sleeps 10
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    Beautiful mountain top wine retreat in Healdsburg!1 / 26
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Grill
    • Patio
    • Washer
    • Housekeeping Included
    • Central Heating
    • Mountain Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 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 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • 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...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    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 95448
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Wine Country Get Away in the Heart.1 / 23
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 2016
    We especially noted the well equipped kitchen--although we didn't take advantage of it fully on this trip. One could devote energy to activities other than restaurants, and plan...
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    About this property
    This beautiful retreat is in the heart of Russian River Valley. Relax on the patio adjacent to the seasonal creek among the vintage oaks and look out to 55 acres of vineyards and the Russian River. Relax and enjoy the lovely common gardens, with lounge seating, fire pit, outdoor dining area while...
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    Healdsburg, Sonoma County 95448
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Healdsburg Contemporary Cottage1 / 8
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Internet Access
    • Balcony
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Terrace
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 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 95448
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    West Dry Creek View1 / 37
    (4)Very good
    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 15 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 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Mountain Views
    • Patio
    • Private Garden
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cottage provides the true Dry Creek Valley wine country experience. with 270 degree views - from Mt. St. Helena in the east to the Pacific Coast Range in the west. Swim in the solar heated lap pool and then relax by the pool while soaking up the view. Walk through the vineyards and the rose...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Hot Tub
    • Balcony
    • Central Heating
    • Grill
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Drive down a tree-lined road. Vineyard is on left, beautiful gardens and bocce court in front, and garden area to the right in which to sit or stroll. Walk into a dramatic entry, and you'll see formal living room and dining rooms on the right, with a half bath across the hallway. To your left,...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Wine Country Cottage1 / 14
    (7)Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    • Hot Tub
    • Patio
    • 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 10 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 95448
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    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 95448
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Housekeeping Included
    • Air Conditioning
    • DVD Player
    • Grill
    • Washer
    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 5 Minutes from Healdsburg Plaza. When you reserve this 2400 square foot, 3 bedroom, 3 bath home, beautiful, panoramic views are just one of the many amenities you will be able to enjoy. The Buena Vista is an...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
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    About this property
    Oenophiles and nature enthusiasts alike will be right at home at this luxury residence situated on a seventeen acre estate vineyard in luscious Sonoma County. From grape vines to mountain pines, the landscape surrounding this stunning vacation rental reflects the quintessential spirit of California...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Parking
    • Grill
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 country, this bright and...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Villa Aix Vineyards1 / 37
    (3)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Housekeeping Included
    • DVD Player
    • Mountain Views
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 January 2017
    We stayed at the Villa Aix Vineyards over New Year's. The villa is perfectly laid out for a party of twelve people (and one dog). The small vineyard is pleasant to walk in...
    Reviewed 11 April 2016
    We rented this house for my girlfriend's bachelorette weekend and it was absolutely beautiful! We were a large group but never left crowded as the house was very spacious...
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    About this property
    Inspired by the Villa Gallici in Aix-en-Provence, Villa Aix Vineyards combines traditional, French cottage warmth with fresh, contemporary farmhouse flair.Nestled on a serene 20-acre vineyard in the Alexander Valley appellation of Sonoma's gorgeous rolling hills, this private estate offers all the...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Internet Access
    • Grill
    • Hot Tub
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 two miles north of central...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4BR/4BA hm w/solar htd pool surrounded by vineyard1 / 30
    (10)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Mountain Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2015
    Mona was just as warm & welcoming as the photos showcased. Celebrating our Mother's 90th, it was the perfect location to enjoy time together as family- plenty of games to...
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    About this property
    'Mona, a name given to house by our daughter when she could not say 'Sonoma,' is a four bedroom/four bath, completely remodeled home including a one bedroom/one bath guest house in the heart of Dry Creek Valley in Healdsburg, California. Our vacation home sits on one acre nestled among the vines...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Mountain Views
    • Children's Pool
    • Patio
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated on 2.5 acres, just minutes from the quaint downtown of Windsor and about 10 minutes from the Healdsburg square, Woody Creek Retreat is at the pinnacle of convenience while offering the serenity of a quiet country luxury farmhouse. Ideal for families, couples, or friends wanting a to...
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    Healdsburg, Sonoma County 95492
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
    • Air Conditioning
    • Parking
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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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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Terra Bella is set in the heart of the beautiful Russian River Valley on Westside road between Thomas George and Porter Creek wineries. This magnificent setting looks out over 55 acres of vineyards bounded by the Russian river. Terra Bella is a 2 1/2 acre property with lovely common gardens to...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • 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....
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 6 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    • DVD Player
    • Parking
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to wine country at this 3BR/2BA home with 360-degree views of gorgeous Dry Creek Valley. Up to six guests can enjoy five-star amenities, luxury outdoor spaces, and so much more. The home’s fresh, modern interiors rival the beauty of the scenic views; an airy, open plan living area blends...
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    Healdsburg, Sonoma County 95448
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 7 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • Balcony
    • Private Garden
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning Modern Villa on eight acres, Located in exclusive Shiloh Estates, only minutes to down town Healdsburg and world class Wineries. Extremely private, Triple gated in a natural setting next to famed Mayacama Gold Course. Fully furnished, high end high thread count linens. 4th bedroom is...
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    Healdsburg, Sonoma County 95403
    Holiday Rental House - 4 Bedrooms, 7 Bathrooms, Sleeps 8
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    Healdsburg Holiday Rentals

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

    Healdsburg a Slice of Paradise

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

    Lots of Activities

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

    Food, Wine and Fun

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

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