Alquileres vacacionales en Healdsburg

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

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.

Wine Country Cottage Walkable to River or Downtown

Centrally located retreat 5 blocks from downtown, Russian River and 3 blocks from at least 9 wineries. Living room fully opens to private deck w/BBQ, outdoor kitchen, dining space and fire place. Gourmet equipped kitchen with many cooking amenities to enjoy wine and a great meal in the garden patio or BBQ outside and relax. Luxury bathroom with heated towel rack, heated floor and bidet. A small cozy two bedroom with many amenities and thoughtful touches.

Farmhouse Villa w/ Captivating Views & Hot Tub

Experience the ultimate Wine Country escape. The property sits on 11 private acres, offering complete privacy, peaceful surroundings, and stunning 360-degree views, including the iconic Mount Helena. Ideally located near Calistoga (15 minutes) and Healdsburg (20 minutes) and surrounded by top-rated wineries. Whether you’re here for wine tasting, relaxation, or a scenic getaway, this property delivers space, comfort, and unforgettable views.

Healdsburg Garden House

Hidden gem Best Value Ideal space for reunions and bridal parties (no events) Clean, Cozy & Private House Near Healdsburg Town Square. 20% discount for self serve rental Healdsburg Kayak Company Discount code - HEALDSBURGGARDEN20 Centrally located for Sonoma county day trips… Covered redwood deck with gas grill 50” HDTVs and fast 1 GB Wi-Fi. Fully stocked kitchen w/ dishwasher. New A/C and heating. TOT #798N

Designer Cottage | Garden Oasis | Walk to Plaza

✓ Fully equipped kitchen. ✓ On-site EV charger. ✓ Lush, private garden. ✓ Dedicated workspace. ✓ Comfortably accommodates 2 guests. ✓ Stylish retreat created especially for couples. ✓ Comfortable Queen Bed with Hotel pressed Sheets. ✓ Just a 4-minute walk to Healdsburg Plaza. ✓ Close to world-class wineries and dining. ✓ Private, architect-designed cottage for two. ✓ Seamless indoor-outdoor living.

Downtown Healdsburg Nest

You can't get any closer to all that Healdsburg has to offer. Just two blocks from the charming Plaza, this fully furnished, upstairs 2 bdr apartment has everything you need for a quick trip to Wine Country or longer-term stay. High-speed internet and all the comforts of home. Steps away from world-class restaurants, tasting rooms, shops, galleries, and music venues.

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!

Dry Creek Valley Cottage

We live in a beautiful rural country setting but we are only a 5-7 minute easy drive into downtown Healdsburg where all the lovely shops, wineries and restaurants are. We invite you to enjoy our lovely garden and taste all the wonderful fruit when it is in season. We have apple, pear, peach, plum, pomegranate, persimmon and citrus trees.

Wake Up at Your Own Private Vineyard - Healdsburg

Unwind at Homefire Sonoma's Winery and Vineyard estate just minutes from Healdsburg Plaza. This 3-bedroom, 2-bath contemporary home sits on 10 serene acres with a 2-acre vineyard, open-plan design, and a fully equipped chef’s kitchen. * If you have 5-star reviews, reach out for possible discount after booking.