Property Category: Healdsburg

Perched above Dry Creek Valley with panoramic vineyard views, this newly furnished private retreat features a pool, hot tub, bocce court, and three exclusive winery tastings included with your stay. Enjoy complete privacy on a quiet country road just 15 to 20 minutes from Healdsburg Plaza. Wine Country seclusion without sacrificing access. ________________________________________ Why Guests Love It • Elevated hillside views across Dry Creek Valley • Private pool and hot tub with…

Welcome to The Dragonfly, a refined Wine Country retreat where luxury, comfort, and privacy come together on a beautiful, vineyard-surrounded estate. Thoughtfully designed for both adults seeking a peaceful escape and families looking for space to relax and reconnect, this sophisticated homestead offers an unforgettable Sonoma County experience. The Space Inside, The Dragonfly features a warm, elegant interior with high-end furnishings, curated artwork, and an open, easy flow throughout the main living…

Experience the beauty of Sonoma County with a stay at this charming farm house. Boasting 3 bedrooms and 3.5 bathrooms, this historic property offers a glimpse into the rich heritage of wine country. As you step inside, you'll be greeted by a spacious gourmet kitchen that seamlessly flows into the dining area, living room, and wrap-around deck. This open layout ensures that everyone can gather together and enjoy the exceptional views that…

Welcome to Healdsburg Homestead! In the heart of Sonoma County’s Dry Creek Valley, this peaceful farmhouse sits along a quiet country road, surrounded by vineyards, gardens, and the gentle sound of a seasonal creek. Though it feels worlds away, you’re just 5 minutes from downtown Healdsburg’s tasting rooms, boutiques, and acclaimed restaurants. Wake up to birdsong and garden views, spend the day wine tasting or paddling on Lake Sonoma, then unwind in…

Hot Tub is in! (pictures coming soon) Our 1880s cottage has been part of Healdsburg’s story for over a century—now it’s ready to be part of yours. Just two blocks from the Plaza, this dog-friendly, standalone cottage blends vintage charm with modern comforts, including Wi-Fi, air conditioning, a dedicated workspace, and a private entrance. Walk to world-class tasting rooms, restaurants, and boutiques, then return to a cozy, character-filled retreat where time slows…

Retreat to the exquisite Heron House, a riverside haven where the towering Redwoods meet the flowing beauty of the Russian River. This special riverfront home offers direct access to a private beach and is located just minutes from downtown Healdsburg. Tucked away on North Fitch Mountain’s wooded knoll, the setting feels wonderfully secluded—yet never far from Wine Country’s vibrant dining and wine scene. There’s a rare calm here: morning mist rising off…

Tucked just eight minutes from downtown Healdsburg, this Luxurious Wine Country retreat invites you to slow down, reconnect, and savor the best of Sonoma County. Wake to peaceful vineyard views, spend sun-filled days exploring nearby wineries, and return home to evenings spent soaking in the hot tub, gathering around the fire pit, or laughing over games long into the night. Thoughtfully remodeled and designed for togetherness, this open-concept estate includes a main…

Escape to Private Vineyard Haven, a luxurious 2BR/2BA Sonoma home where modern comfort meets vineyard charm. Spanning 1,439 square feet, the home features a gourmet chef’s kitchen and floor-to-ceiling folding glass doors that open completely, blending indoor living with stunning views of your private Sauvignon Blanc vineyard and California sunshine. This home offers a perfect blend of comfort and care. Guests enjoy all the amenities while experiencing hospitality that makes them feel…

Nestled between towering redwoods and rolling vineyards, Puccioni Paradise offers an intimate Wine Country escape for couples or solo travelers seeking tranquility and romance. Just 15 minutes from Healdsburg Plaza's renowned restaurants and tasting rooms, this peaceful sanctuary combines modern comfort with natural beauty—perfect for romantic getaways, remote work retreats, or wine lovers seeking privacy. Sleeps 2-3 guests: Ideal for couples, with optional third guest accommodations available for an additional fee. The…

Escape to Redwood River House, a beautifully updated 2-bedroom, 1-bathroom riverfront cottage along the Russian River, just 1.5 miles from downtown Healdsburg. Thoughtfully designed for couples, small families, or friends, this inviting Wine Country retreat pairs peaceful river views and mountain scenery with modern comforts and easy access to town. Here, mornings begin with coffee on the deck, days unfold on the river or exploring nearby wineries, and evenings wind down in…

Tucked along the Russian River, just 1.5 miles from Healdsburg Plaza, River View Lodge is a private, peaceful retreat perfect for romantic getaways, family vacations, or remote work with a view. With stunning river frontage, a private dock, two kayaks, a hot tub, and an expansive deck over the water, this home offers an unforgettable Wine Country experience. While this home impresses with its comfort and setting, it’s the personal touches that…

Relax and recharge at Riverbend Retreat, a warm and inviting 3-bedroom, 1.5-bath bungalow nestled in a peaceful neighborhood just 5 minutes from Healdsburg Plaza. Perfect for couples, families, or a group of friends, this home blends rustic charm with modern comfort, offering an ideal base for exploring Sonoma wine country or simply unwinding by the river. Guests love the comfort and charm of our home, but it’s the thoughtful hospitality that keeps…

Slow down, unplug, and breathe in the beauty of riverfront living at Rivers Breeze, a charming 2-bedroom, 1-bath main house with a private 1-bedroom, 1-bath lower-level suite, nestled along a peaceful stretch of the Russian River, just minutes from downtown Healdsburg and nearby wedding venues. Perfect for couples, families, or friends, this retreat invites you to reconnect with nature, loved ones, and yourself. We pair the comfort and charm of the home…

Escape to Sanctuary on Lytton, an extraordinary 11.67-acre estate in the heart of Alexander Valley, just 7 minutes from Healdsburg Plaza. This exclusive retreat offers ultimate privacy, breathtaking mountain and valley views, and a serene bird refuge, making it ideal for family reunions, friends’ getaways, corporate retreats, or creative workshops. Enjoy all the comforts of a beautifully appointed home, enhanced by our attentive hospitality. We provide guidance, thoughtful touches, and support to…

Escape to Santini, an exclusive farmhouse estate in the heart of Dry Creek Valley, just 8 miles from Healdsburg Plaza. Surrounded by world-class vineyards, this newly built home combines seclusion, comfort, and modern luxury, making it perfect for families, couples, or groups of friends seeking a Wine Country retreat. This home offers a perfect blend of comfort and care. Guests enjoy all the amenities while experiencing hospitality that makes them feel warmly…

Serenity on Dragonfly is a charming 3-bedroom country home nestled in the heart of Wine Country, just minutes from the vibrant Healdsburg Plaza with its top-rated restaurants and renowned tasting rooms. Merriam and Limerick Lane wineries are within walking distance, offering a truly immersive wine country experience. Beyond the stunning home and location, our guests love the personal touch we provide. We’re attentive, responsive, and committed to making sure your Wine Country…

Escape to Your Private Vineyard Estate Just steps from Trentadue Winery, this single-level retreat offers the ultimate Wine Country getaway. Surrounded by sweeping vineyard views and open Sonoma skies, enjoy relaxed luxury with a private pool, spacious interiors, and complimentary tastings at four renowned wineries. Ideal for couples, families, or friends traveling together, the home combines historic charm with modern comfort — all just minutes from downtown Healdsburg. The Experience Wake up…

Rental Property DescriptionWelcome to your own slice of Wine Country magic. Just minutes from downtown Healdsburg, this private retreat is all about easy living, beautiful views, and time well spent—whether you’re here to celebrate, reconnect, or simply slow down and soak it all in. Inside, the home is bright, comfortable, and made for gathering. The chef’s kitchen is ready for everything from lazy breakfasts to celebratory dinners, stocked with quality appliances, cookware,…

THE SPACE Walk to the historic Healdsburg Plaza from this modern single-level farmhouse. Vineyard Vue features 2 king en-suites, a chef’s kitchen, a wraparound porch, and vineyard vistas. Enjoy complimentary wine tastings at Merriam Vineyards, Orsi Family Vineyards, and Croix Estate. Your Wine Country Retreat Where urban sophistication meets wine country charm, Vineyard Vue is a beautifully remodeled farmhouse just blocks from downtown Healdsburg. Blending character, comfort, and breathtaking vineyard views, it’s…

Discover Xanadu Healdsburg, a stunning Blu Home retreat in the heart of Sonoma County Wine Country. Perfectly located just 5 minutes from Healdsburg Plaza, you’re steps from world-class wineries, award-winning restaurants, and boutique shopping across the Dry Creek, Alexander Valley, and Russian River regions. This eco-conscious luxury home combines modern design with green solar technology, offering one-level living with seamless indoor-outdoor flow through glass-walled Nano doors. The great room, gourmet kitchen, and…

Step into Fitch Street Escape, a chic and recently remodeled historic home just 2 blocks from Healdsburg Plaza. Perfectly located in the heart of Sonoma Wine Country, this sophisticated retreat offers easy access to award-winning restaurants, boutique shopping, and world-class wine tasting. Blending modern design with historic charm, this bright, open-concept home features 2 bedrooms, 2 full bathrooms, and high-end finishes throughout. A chef’s kitchen with stainless steel appliances, sleek surfaces, and…