Pet-friendly holiday rentals in Healdsburg

Stunning Sauna Cottage Retreat on Private Vineyard

Welcome to our private, renovated, personal spa in the woods. Including a large wood-burning Finnish sauna, it features a picturesque deck with hot/cold plunge over breathtaking untouched forest with fire pit vineyard-side. This all-cedar cottage is nested below Halleck Vineyard, one of Sonoma County’s prestigious wineries. A perfect retreat, you are centrally located for the best Sonoma has to offer Sonoma County Wine Tastings (0-20 mins) Bodega Bay (20 mins) Armstrong Giant Redwoods (30 mins)

❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤

❤New! Welcome to the "The Elegant Barn", our newly built stylish Barn Cottage in the HEART of wine country! Our *INSTAWORTHY* barn cottage boasts a HOT TUB, panoramic vineyard VIEWS, comfy furnishings & convertible glass indoor/outdoor doors to bring the outdoors inside! LOCATION, LOCATION, LOCATION! Set on a historic vineyard property on Dry Creek Road, the location of Healdsburg's most famous wineries, and an easy walk, bike ride or drive to many of the best wineries in the area! PETS OK!❤

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

Elegant & Spacious Luxury Wine Country Estate

The perfect place for your group to stay in Wine Country! Featuring two large entertaining areas and an additional dining room, this is a great place for fun and relaxation! Play ping pong, pool or poker in our game room, or dine on our spacious patio under the pergola! Relax and soak in our hot tub and enjoy the zen gardens and tranquil water feature, or sip on a glass of wine by the outdoor fire pit. Close to the Sonoma County Airport, wineries, and world-class dining. Welcome home!

Eco Luxury Private Sanctuary / The Farmhouse Oasis

**Very Important** Please read description below and “Other things to note” at the bottom of this section before contacting us. • Adults Only • Private Sunny 1 Bedroom, 2 full bathroom 900 sq ft stand alone home • Private Backyard with Pool, Sauna, Outdoor Shower, and Outdoor Bathtub • Luxurious Modern Farmhouse Style • Created to feel like a boutique hotel experience • In the heart of wine country Sebastopol/ West Sonoma • Eco-Friendly products used • Strict cleaning protocols

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.

Three-Building Healdsburg Homestead with Wine Barn

Your Healdsburg Homestead for launching wine country adventure! Recently remodeled, 3 buildings on 1/2 acre, including a barn with a winetasting bar & game room! Great for families and groups. Perfectly located for cycling on the legendary Eastside/Westside loop. For wine lovers, we are across the street from Rodney Strong Vineyard and the amazing sparkling wines of the beautiful J Vineyard. Best of all, Healdsburg Plaza is just a short hop away!

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.

Country Carriage House in Downtown Geyserville

Linger over coffee on your quaint patio amongst 6 acres downtown in sweet Geyserville. An industrial loft vibe with wine country bones—the cottage is modern/rustic meets country-correct. Immerse yourself in country life or walk to downtown Geyserville for an Aperol Spritz. Truly where design meets refuge. Goats, horses, dogs, one heifer 🐄 named Francis, and one farm cat named Leo on property. Fully fenced front yard and back patio!

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.

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