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Magical Wine Country Compound – Epic Views & Pool

Escape to a Magical Wine Country Retreat Perched atop a hill with sweeping views of 47 private acres, this newly renovated and impeccably styled compound offers the ultimate blend of seclusion and sophistication. Soak in sunsets from the heated pool or unwind in the hot tub under the stars. Justminutes from the charming towns of Geyserville and Healdsburg, enjoy a balance of quiet countryside and vibrant wine country food, drinks and culture. Relax, connect, and create unforgettable memories!

Oak & Hill | Sonoma-Napa Private Retreat + Hot Tub

Rated in the top 5% Guest Favorites, this modern country home offers luxury and classic California indoor-outdoor living. Set on an expansive sun-filled lot with lawns, fruit trees and a garden, it is framed by peaceful low hills on three sides. Explore over 250 Sonoma and Napa wineries, hot springs, beaches, rivers, and redwood forests all within 30 miles. While private, Santa Rosa city amenities are just 10 minutes away. Ideal for wine country getaway, wedding trip, remote work or staycation.

Chalk Hill 360°

Perched atop a hill in the Chalk Hill region of Healdsburg, we designed our house to be the kind of place where you immediately feel at home and never want to leave. The 4 bedroom main house features expansive views, a bright open floor plan and ample spaces for gathering indoors and out including an oversized poolside lounge bed and outdoor dining area. Note that we are only renting to guests (8 max) who want a relaxing getaway & agree to our rental rules. No parties. TOT618N | LIC24-0442

New! The Quails Crossing- Healdsburg Vineyard Home

Brand new modern luxury home designed to maximize the natural beauty & surrounding calm. Perched on a hill surrounded by 100 year old oak trees, this spectacular home was built facing beautiful rolling hills and vineyards with ultimate guest comfort in mind. Enjoy your AM coffee watching a family of quails roaming the vineyard and end your evening with a glass of wine on the deck watching the sun set behind the golden vineyard hills. Located approx 3.5 miles (6min) from the Healdsburg Plaza.

10 Acre Estate with Views, Teahouse, and Picklebal

Discover a private paradise at this 10-acre estate. Surrounded by a hobby vineyard, oak woodlands, and seasonal creeks, this property is a destination in itself. Unwind in the Japanese teahouse, play on the private tennis and pickleball courts, or take in the views from the outdoor patio. The beautifully appointed home features fireplaces, a gourmet kitchen, and a deck overlooking the landscape. It's an unparalleled retreat for relaxation, recreation, and exploring the best of Sonoma County.

Calistoga Mansion - 38 Acres | Lap Pool | Views

Escape to your own private 38-acre luxury retreat in pristine Calistoga wine country, with sweeping vineyard views and resort-style amenities. Designed for up to 16 guests, the estate features a main house over 5,000 sq ft, private guest house, 75-ft lap pool with optional heating, outdoor kitchen and bar, game rooms, serene pond, and so much more. Enjoy exceptional privacy ~20 minutes north of downtown Calistoga perfect for upscale getaways to Napa Valley, Sonoma Valley, or even Healdsburg!

Wine Country Estate

Unique wine country massive estate will delight you and multiple guests. Enjoy a tennis court, two pickle ball nets, traditional rose gardens and acres of private land to roam as well as huge rooms for enjoyment. The home is large with 5 bedrooms all with en-suite bathrooms. Enjoy 2 king rooms, 1 queen room and 2 rooms with single beds. All rooms are air conditioned, sound proofed and equipped with the fastest Starlink internet. Please note the pool is NOT heated and there is NO hot tub.

Luxury Villa, Pool, Spa, BBQ, By Healdsburg Sonoma

Top 5% of homes, Luxe badge, and guest favorite badge by Airbnb. Welcome to Villa Montage - Brand new, luxury 4br/3.5ba Villa in the heart of Sonoma. Close to Wineries & Healdsburg. An award-winning architecture firm in SF designed the house. ☞ New & modern home ☞ Pool & Spa (Pool heated April-Oct) ☞ Outdoor & Indoor fireplaces ☞ Pool table ☞ BBQ with covered patio and dining table ☞ Chef's kitchen ☞ Baby-friendly (crib, toys, monitor) ☞ Tesla Charger ☞ IG @Villamontage.sonoma

The Estate Villa

We built your dream! The Estate Villa at NewTree Ranch is perfect for intimate weddings, celebrations, corporate retreats, board meetings & family & friends vacations! We're here to assist you with all your weekend celebration plans, from curated dining experiences to unforgettable activities. Our luxury villa sleeps 8 and offers access to unique ranch experiences. Add another villa with 2 bedrooms to accommodate a total of 12 people.

The Overlook by Sonoma Stays – Modern Luxe Retreat

Set on nearly eight acres in the quiet hills of Santa Rosa, this spacious and modern 5-bedroom, 4-bath home offers comfort, privacy, and stunning scenery. Perfect for families or groups, it features a pool and spa, private yoga studio, bocce court, and beautifully landscaped grounds. With open living spaces, natural light, and contemporary design, there’s plenty of room to relax and enjoy moments with friends and family.

Modern, private Healdsburg oasis

Recently constructed in 2020, our 5 BR house is located on 50 acres with vast views. Less than 15 minutes to Healdsburg Square, but a world away. You will have privacy and serenity, but not isolation. Enjoy indoor/outdoor living at its finest at our home, designed to be sustainable and integrate with the natural surroundings, including plentiful redwoods and madrone trees. 50+ 5-star reviews on a different platform.

Dry Creek Wonderland | Private Farm Estate in Wine

Welcome to our gracious home and honey farm in Healdsburg. - 4 bedrooms, 4 bathrooms, sleeps 8 - Open living space with seamless indoor-outdoor flow - Fully equipped kitchen and spacious dining area - Outdoor patios with BBQ grill and countryside views - Unique farmstay experience with educational tours available - Easy access to wineries, farmers markets, and hiking