Cynthia, Tesia, and Carlos are your dedicated owners and hosts at Healdsburg Hilltop Villa, otherwise known as The Bella Villa Messina. Cynthia, originally from San Diego, is a proud mom and business owner who brings her love of travel and experience in hospitality into creating a smooth, thoughtful guest experience. Tesia, a NorCal native, loves dancing, adventures, and her sweet pup. She brings warmth, creativity, and attention to detail to every guest stay. Carlos, from Reno, Nevada is your on-site property manager and go-to guy for anything that needs a skilled hand. He is also a full time golf caddy and a pilates instructor at a local hot pilates studio. Together, we’re here to make your Wine Country stay relaxing, memorable, and effortless.

You may find it hard to leave this enchanting, one-of-a-kind escape. Welcome to Healdsburg Hilltop Villa—a beloved gem, formerly voted the #1 Bed and Breakfast on TripAdvisor for multiple years, now beautifully refreshed under new management. Nestled in the hills above Healdsburg, this historic villa offers private en-suite rooms, optional chef-prepared meals, a relaxing hot tub, and a shallow pool uniquely set within a restored aqueduct once connected to the iconic Simi Winery. Share in the charm: The villa features thoughtfully curated guest rooms, each with a private bathroom, soft and clean linens, and unique touches. Common spaces include a sun-soaked breakfast veranda, cozy sitting areas, lush gardens, and an open-air dining terrace perfect for golden-hour wine tastings. Whether you're gathering by the pool and hot tub, taking in sunset views, or enjoying a peaceful moment in the garden, every corner invites you to slow down and savor wine country living at its finest.

Villa on the Hilltop is nestled in one of Healdsburg’s most serene and sought-after neighborhoods. Perched above the town, this hillside enclave offers sweeping views of the Russian River Valley, providing a tranquil retreat while remaining just minutes from downtown Healdsburg. The surrounding area is characterized by luxury estates, boutique vineyards, and a peaceful, rural atmosphere. Residents and guests enjoy the perfect balance of seclusion and accessibility, with nearby access to renowned wineries, gourmet restaurants, and charming shops that define Healdsburg’s appeal. This neighborhood is ideal for those seeking a quiet, upscale environment with the convenience of being close to the vibrant heart of Sonoma County’s wine country.