Alquileres vacacionales en casas en Healdsburg

Sonoma Retreat-Pool, Spa, Barn, OD Fire & Kitchen

Escape to a private 1.3-acre wine country retreat in Sebastopol, minutes from Russian River wineries, Occidental & downtown. Lounge by the heated pool, soak in the hot tub, and pick apples from your own Gravenstein orchard. Fire up the grill under the stars, then head to the game barn for air hockey, movie project, Jenga, darts and kitchenette. Walk the expansive outdoor space with plenty to do for all ages. Pet- & family-friendly, EV charging, fast WiFi — a designer retreat built for gathering.

Chic Wine Country Stay - Walk to River & Downtown

Discover our cozy two-bedroom retreat, just minutes from downtown. This charming space features top-quality cooking items, a bidet, and a heated towel rack. Enjoy seamless indoor-outdoor living with doors that open to a deck, complete with a BBQ and outdoor dining area. Located across from scenic walking trails and only four blocks from the Russian River, it's the perfect spot for nature lovers. Despite its small size, every detail is thoughtfully designed for your comfort. Book your stay today

Healdsburg House - Chiquita Road

Relax with the whole family at this peaceful and private home mins to the Healdsburg Square, Montage Resort, and Dry Creek/Alexander Valley Wineries. The updated home features an open concept kitchen, two family rooms, and a sparkling hot tub on 1.5 private acres surrounded by vineyards and oak trees. Cruise your bike to town or head directly out Chiquita Road to some of the world's greatest cycling. 2.4 miles to the Montage Resort. 2.5 miles to the Healdsburg Square. Welcome to Wine Country!

Dry Creek Ranch ~ (Tariff Discount) Hot Tub & Pool

Enjoy an idyllic wine tasting weekend for 3-4 couples, have fun with the whole family (pets welcome) or find adventure along the world famous Dry Creek Road. This property boasts a main house, pool house & Game barn. The main house sleeps 10. The pool house features a 70” flatscreen, a Live Edge tasting bar and Lanai. The property is only 1.4 miles from Healdsburg’s square. Take a gentle bike ride into town or stay put – pour wine, soak in the hot tub, and watch the sun set over the vineyards

Healdsburg 2br Cottage with Private Yard!

Relax at our renovated private guesthouse a 5 min drive (1 mi) from the Healdsburg Plaza. Updated 2 br/ 1 ba home with private yard and outdoor dining and lounge areas. Our layout is ideal for one family or close friends traveling together as the one bathroom is accessed through the primary bedroom. Perfect for a wine country getaway- convenient location just outside of Healdsburg city limits in a vineyard adjacent neighborhood. We love kids and welcome them! Permit #TVR22-0119

Wine Country Villa Heated Pool Hot Tub Upper Level

Welcome to Brush Creek, 20-minutes from Sonoma, Napa, Russian River, Alexander, and Knight's Valleys. Our cozy villa offers 2 unique bedrooms, including a regal King Master suite and a second King bedroom. Complimentary EV charging. Healdsburg, Calistoga, and the trendy Barlow are easily accessible. Brush Creek: where comfort, luxury, and character converge for an unforgettable wine country retreat. Heated Pool (fees may apply). No one else in the property during your stay. SVR26-101

Vineyard Vista, Modern Farmhouse Cottage with Pool

Our architect remodeled (2021), five star, elegant Farmhouse with great room and fireplace, is simply perfect throughout. This unique wine country two-acre property, with heated swimming pool (for a fee), looks out to the beautiful Russian River vineyards and the never-ending Western panorama. Only minutes from award winning food and shopping in downtown Healdsburg, it’s within easy walking or bicycling distance of tasting rooms at J, Rodney Strong and other acclaimed Sonoma wineries.

Vineyard views, hot tub, sauna, cinema

Peaceful two-level house overlooking Dry Creek Valley vineyards. A winery a few doors away and Healdsburg Square 8 minutes away. Big deck for sunsets over the vines, fireplace living room, and a full private spa: hot tub, sauna, cold plunge, gym and massage table. Sleeps 6 across 3 rooms - king master suite and queen guest suite (both ensuite), plus a playroom with queen daybed and bunk. Media room for movie nights, EV charger, Starlink wifi. Questions? I reply fast!

Modern Healdsburg Retreat • Hot Tub, Bocce & Views

Vineyard views + hot tub under the stars—modern Healdsburg, 5 min to the Plaza. Set in Dry Creek Valley, this design-forward retreat feels a world away—yet you’re minutes from top wineries, tasting rooms, and dining. Slow mornings with coffee overlooking the vines. Golden-hour dinners outside. Evenings in the hot tub with sunset views and total privacy. Designed for relaxed Wine Country living with bocce, outdoor lounge spaces, and seamless indoor-outdoor flow.

Peaceful location, hot tub, fire pit, game room!

Feel your stress melt away as you wind your way down a country road to our little piece of heaven in wine country. Our cozy home is a great starting place for your Healdsburg adventures! Private yard, super comfortable beds, well equipped kitchen, cozy living room with fireplace, free wifi and cable, game room with pool table, poker, Skee-ball plus a wonderful outdoor dining area. Just a 5 minute drive to downtown Healdsburg.

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court

Escape to a private and peaceful retreat surrounded by Russian River Valley Chardonnay and olive trees. Set on 10 acres of producing vines, our cottage offers vineyard views, a bocce court, fire pit, garden, cruiser bikes, and a sparkling hot tub. Immerse yourself in world-class food, wine, cycling, and nature. Your perfect wine country escape awaits!

Modern Home in Hburg Wine Country

Located within miles of the Healdsburg town square, enjoy this 3 bedroom/4 bath home with expansive decks and large open spaces. A perfect balance of indoor-outdoor living. * Please note: per City of Healdsburg code, home rental is permitted only for durations >30 days within the city limits. Please message me with any questions about this.