Cynthia and Tesia are the dedicated owners and hosts of Healdsburg Hilltop Villa, also known as Bella Villa Messina, a private Wine Country estate villa and boutique hotel. Cynthia, originally from San Diego, is a proud mom and seasoned hospitality professional who brings her love of travel and guest experience into every stay. Her focus is on creating seamless, elevated experiences for couples, families, and groups visiting Sonoma County. Tesia, a Northern California native, is known for her warmth, creativity, and thoughtful attention to detail. From personalized recommendations to ensuring every space feels inviting and comfortable, she helps guests feel at home from the moment they arrive. Together, Cynthia and Tesia are committed to making every stay easy, memorable, and beautifully hosted. Whether you’re planning a romantic getaway, wine tasting weekend, wedding, retreat, or private group stay, they’re here to help you create an unforgettable Healdsburg Wine Country experience. Inquire directly for exclusive-use estate bookings, weddings, retreats, and group stays.

You may find it hard to leave this enchanting, one-of-a-kind Healdsburg estate villa. Welcome to Healdsburg Hilltop Villa, a beloved boutique hotel–style estate, formerly voted #1 Bed and Breakfast on TripAdvisor for multiple years, now beautifully refreshed under new management. Perched in the scenic hills above downtown Healdsburg, this historic Wine Country estate villa blends old-world charm with boutique hospitality. Guests enjoy private en-suite rooms, optional chef-prepared breakfasts, a relaxing hot tub, and a serene shallow pool set within a restored historic aqueduct once connected to the iconic Simi Winery. Each thoughtfully curated guest room features a private bathroom, crisp linens, plush bedding, and unique details designed for comfort and rest. Inviting common spaces include a sun-filled breakfast veranda, cozy sitting areas, lush gardens, and an open-air dining terrace ideal for sunset wine tastings and gatherings. Whether you’re unwinding by the pool and hot tub, taking in sweeping vineyard and sunset views, or enjoying a peaceful moment in the gardens, this luxury Healdsburg boutique hotel and private estate invites you to slow down and savor Sonoma County wine country living at its finest. The estate is ideal for romantic getaways, wine tasting weekends, weddings, retreats, and private group bookings. Inquire directly for wedding, retreat, and exclusive-use estate reservations.

Villa on the Hilltop is nestled in one of Healdsburg’s most sought-after hillside neighborhoods, offering a rare blend of privacy, scenery, and proximity. Perched above town, this Healdsburg hilltop estate features sweeping views of the Russian River Valley, creating a peaceful retreat just minutes from downtown Healdsburg. The surrounding area is known for luxury Wine Country estates, boutique vineyards, and a serene rural atmosphere that defines the best of Sonoma County living. Guests enjoy the feeling of seclusion while remaining close to world-class wineries, acclaimed restaurants, tasting rooms, and charming local shops. Ideal for travelers seeking a quiet, upscale Wine Country escape, this neighborhood offers the perfect balance of tranquility and convenience. Whether you’re visiting for wine tasting weekends, romantic getaways, weddings, retreats, or private group stays, Villa on the Hilltop places you at the center of Healdsburg’s luxury Wine Country experience.