Places to stay near Healdsburg Plaza

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!

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

Eagle's Nest Treehouse Farm Stay

Eagle's Nest Treehouse Farm Stay is a tranquil, secluded, luxurious, romantic wilderness experience in a private forest on a 400 acre working ranch. Thirty feet above the forest floor you are nestled in a gorgeous, well-appointed suite of 1,000 year old polished redwood, with bathroom and amazing copper/glass forest-view shower. Explore hiking trails through the forest and learn about ranch operations (Highland cattle, goats and ducks). See guest comments in the space description.

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.

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

Luxurious, Private, Healdsburg Guest Cottage

1083 Guest House is comfortable luxury in a spacious private cottage within walking distance of four-star restaurants, wineries, fabulous boutique shopping, and the Russian River. Your secluded cottage is nestled in the trees with views of a wooded area and is the perfect base for your Wine Country get away. There is no stove/oven due to zoning/licensing so the cottage has a microwave, small air fryer, toaster and bbq.

Romantic Cottage | Walk to Healdsburg Plaza

Welcome to this light-filled cottage in a friendly historic neighborhood, just a short walk from the Healdsburg Plaza. Enjoy coffee or local wine at the private garden picnic table, relax in Adirondack chairs, or gather around the fire pit on cool evenings (weather permitting). Walk to town for wine tasting and dining, bike quiet back roads, hike nearby redwood trails, or take a scenic drive to the Sonoma Coast.

Designer Cottage | Garden Oasis | Walk to Plaza

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

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!

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.