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)

Alexander Valley: Wine Lover and Cycling Paradise

The Finca Guest House is a beautiful modern & private unit, which offers country seclusion just a short hop into Healdsburg. Three private outdoor spaces for your use! Coffee patio, wine patio, goat patio--your choice! World-class biking out the door. Guest House will be thoroughly cleaned per Airbnb guidelines! *This property has farm animals so no outside animals allowed. See Rules and Policies notes Gas grill w/burner is available for outdoor cooking. NO full kitchen. Sonoma Co. TOT#3191N

❤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!❤

2 Bedroom Flat In Downtown Healdsburg

Enjoy a stylish experience at this centrally-located upstairs apartment. Tucked away in a building surrounded by restaurants, bars, and tasting rooms just a few blocks from the historic downtown plaza this art gallery meets air B&b focuses on the intersection of modern art and ancient tradition. You'll find paintings, sculptures, and artistic touches around every corner of this luxuriously modern flat. Enjoy exceptional accommodations with two separate bedrooms, each with a queen-sized bed.

Bucher Vineyard Studio

Experience the best that wine country has to offer with a stay in our newly remodeled studio apartment, nestled on a historic vineyard on Westside Road in the heart of the Russian River Valley. Located just 5 miles from downtown Healdsburg, you’re close to Michelin-rated restaurants, or you can cook in the fully equipped kitchen. Relax in our beautiful outdoor space or take a stroll through the scenic vineyards. Enjoy the perfect blend of tranquility & convenience at our vineyard retreat.

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

Dry Creek Retreat- Bocce, Hot Tub, EV Charger

Ideally located 5 minutes from the Healdsburg Square on Dry Creek Road, this home is the perfect place for restoration or play! The modern home boasts spectacular vineyard views on a magical 1/2 acre lot, a hot tub, Bocce ball court, large deck, and a fully stocked kitchen. World class food, wine, cycling, and nature are at your fingertips here! -5 minutes to the Healdsburg Square with restaurants, tasting rooms, and shopping -10 minutes to dozens of wineries

Gracianna Winery Vineyard Loft - Farm Stay

Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile of Pinot Noir in Healdsburg includes equipped kitchen with new gas Wolf Range. Pick up breakfast needs before arriving. Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. LOFT AVAILABLE YEAR ROUND. TOT #3294N

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. Guests staying 3+ nights will receive a complimentary bottle of Chardonnay crafted from our vines. Your perfect wine country escape awaits!

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 and bidet. A small cozy two bedroom with many amenities and thoughtful touches.

Healdsburg Contemporary Cottage With Lush Backyard Patio

Your private Healdsburg retreat—just a 4-minute walk to downtown wine tasting rooms, restaurants, shops, and the Farmers Market. This stylish guest cottage offers parking in front of a private entry, garden with al fresco dining, BBQ, lounge area, and a fully equipped Pilates studio. Designed with international contemporary art and thoughtful touches, it’s perfect for a weekend escape or a longer stay while house hunting.

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.