House vacation rentals in Healdsburg

4.99 out of 5 average rating, 135 reviews

The exterior of a charming Victorian house is visible, featuring a welcoming front porch with a green door. Lush greenery and colorful plants frame the entrance, and a rustic wooden cart is placed nearby on a gravel pathway, enhancing the inviting outdoor space.

Home in Windsor

Gorgeous Victorian in the HEART of Windsor

Gorgeous renovated Queen Anne Victorian located in the heart of Windsor, CA combines quality finishes, modern convenience & vintage details. With a stylish kitchen, high ceilings, 3 beds/2 baths on a single level, HVAC & a huge lot with a Bocce Court. Walking distance to the Town Green, restaurants, wine tasting rooms and shopping. Just 3.5 miles from the Sonoma County Airport (STS), 5 miles to downtown Healdsburg, in the heart of the Russian River Valley & just 57 miles from the Golden Gate.

ValueLocationWalkability

An airy living space is highlighted by high-beamed ceilings and large windows, allowing plenty of natural light. A gray sofa and two brown leather chairs are arranged around a round coffee table on a light-colored rug. The adjacent dining area features a wooden table, surrounded by various chairs.

5.0 out of 5 average rating, 125 reviews

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!

FamilyLocationTV

An expansive outdoor patio area features modern metal furniture and a covered dining table, inviting al fresco meals. Large sliding glass doors create a seamless flow between indoor and outdoor spaces, with a view of the surrounding natural landscape and vineyard beyond.

4.97 out of 5 average rating, 146 reviews

WineCamp - Wine Country - Vineyard View Hot Tub

The WineCamp concept is rooted in the rural ambience of working local vineyards and craft breweries. This purpose-built residence offers indoor/outdoor living at it best. Conceived as the ideal space for two adult couples, the spacious dual master suites are separated by gracious open-plan living areas that flow seamlessly through multi-panel sliding walls of glass onto the terrace with Sundance spa hot tub and vineyards beyond. This wine and beer themed property is not suitable for children.

ValueLocationWalkability

Superhost

An aerial view reveals a spacious property surrounded by lush vineyards. The main house is situated to the left, with a sparkling pool adjacent to it. A winding road leads through the greenery, while gentle hills stretch into the distance under a clear blue sky.

4.89 out of 5 average rating, 108 reviews

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

LocationValueCondition

A modern living area showcases a comfortable gray sectional sofa and two accent chairs. A round wooden coffee table sits in the center, with a small plant adding a touch of greenery. Soft lighting is provided by a ceiling fixture and table lamps, enhancing the inviting atmosphere.

4.92 out of 5 average rating, 157 reviews

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

LocationValueAmenities

The exterior of a beautifully designed house is presented, showcasing a light-colored facade with decorative shutters and a newly paved pathway. A stone fountain serves as a focal point amidst landscaped greenery, highlighting the inviting entrance and two stories of windows.

4.97 out of 5 average rating, 111 reviews

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

ValueLocationBiking

The exterior showcases a landscaped garden featuring diverse greenery, decorative rocks, and a serene stone pathway. A gazebo is positioned in the garden, complementing the house’s two stories, which are framed by trees and plants. The scene is illuminated by soft natural light.

4.97 out of 5 average rating, 244 reviews

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!

FamilyLocationQuiet

The ranch-style home is surrounded by landscaped gardens, featuring a driveway that curves gently towards the entrance. The exterior showcases a combination of light-colored siding and brick accents, with large windows allowing natural light to fill the interior spaces.

4.93 out of 5 average rating, 302 reviews

The Wine Ranch

The Wine Ranch Just five minutes north of Healdsburg Plaza, The Wine Ranch is a beautifully remodeled ranch-style home, set on over a half acre of lush outdoor space. The property features a bocce ball court, ping-pong, an expansive deck and patio perfect for al fresco dining or tranquil relaxation. Designed to host gatherings, the spacious living room, dining area, and gourmet kitchen create an inviting atmosphere for couples, families, or groups of up to eight friends.

LocationValueParking

4.93 out of 5 average rating, 180 reviews

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.

LocationFamilyPets

A pathway leads to a welcoming front porch, flanked by greenery and blooming flowers. The light-colored home is partially shaded by surrounding trees, creating a serene approach. The yard features fresh landscaping with mulch and various plants, enhancing the inviting entrance.

4.88 out of 5 average rating, 365 reviews

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.

FamilyValueAccuracy

4.93 out of 5 average rating, 659 reviews

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

ValueFamilyCondition

A hot tub is positioned on a grassy area, offering a view of rows of grapevines against a serene sunset. Colorful flowers are visible nearby, complementing the natural surroundings.

5.0 out of 5 average rating, 275 reviews

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!

FamilyValueWalkability

Popular amenities for Healdsburg house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A heated swimming pool reflects the early evening sky, surrounded by lush greenery. Comfortable lounge chairs are positioned around the pool, complemented by a shaded umbrella. The vineyard is visible in the background, enhancing the peaceful atmosphere of this outdoor space.

4.93 out of 5 average rating, 134 reviews

Vineyard Vista, Modern Farmhouse Cottage with Pool

LocationFamilyView

4.98 out of 5 average rating, 121 reviews

A serene outdoor space is showcased, featuring a sparkling pool surrounded by neatly arranged white lounge chairs. Lush greenery and blooming shrubs create a natural border, enhancing the tranquil atmosphere.

Home in Geyserville

Historic Home; Walk to Cyrus, Diavola, Catelli's

FamilyValueParks

5.0 out of 5 average rating, 726 reviews

A private backyard features a solar heated swimming pool surrounded by lounge seating and potted plants. A tiki bar is visible in the background, with palm trees providing shade in the sunlight. The space combines relaxation and outdoor living for a serene atmosphere.

Home in Graton

Eco Luxury Private Sanctuary / The Farmhouse Oasis

LocationFamilyBackyard

An expansive backyard is shown, featuring a sparkling pool surrounded by a stone patio. A gazebo offers shaded seating, while a cozy fire pit creates an inviting gathering space. Lush greenery and trees frame the scene, enhancing the tranquil setting of the home.

4.96 out of 5 average rating, 102 reviews

5-Bedroom Creekside Wine Country Retreat

FamilyLocationNearby

4.89 out of 5 average rating, 118 reviews

The serene pool area is surrounded by lush greenery, featuring modern lounge chairs and large umbrellas for shade. The sparkling water invites relaxation, while a covered outdoor space extends from the home, providing a seamless transition to the tranquil outdoor retreat.

Home in Sebastopol

Serene Wine Country Retreat with Pool & Hot Tub

FamilyLocationAmenities

A Mediterranean-inspired house is set amidst lush gardens and rolling hills. The round swimming pool is surrounded by colorful landscaping and lounge chairs, inviting relaxation. The exterior features warm stucco walls and a tiled roof, showcasing a harmonious blend with the natural surroundings.

4.99 out of 5 average rating, 141 reviews

Wine Country Luxury Retreat - Pool Sauna Spa Views

ValueFamilyBathroom

4.87 out of 5 average rating, 126 reviews

The image displays a sunny outdoor pool area surrounded by comfortable lounge chairs. Two shaded cabanas offer shelter, while vibrant orange and red canopies provide additional shade. Lush green hills are visible in the background, contributing to a serene atmosphere.

Home in Cloverdale

Woodhawk Manor of Alexander Valley

ValueLocationParking

4.97 out of 5 average rating, 120 reviews

The home is framed by lush greenery and vibrant plants, with a patio featuring outdoor furniture. Warm light spills from the windows, hinting at a cozy interior. A barbecue grill is positioned nearby, providing an inviting space for outdoor gatherings.

Home in Kenwood

Vineyard Haven: Pool, Hot Tub & Wine Country Charm

FamilyLocationPool

House rentals with a hot tub

A spacious deck features comfortable seating arrangements with wicker chairs and side tables. A large dining table is positioned under an umbrella, providing a shaded area for meals. Lush greenery and vineyards are visible in the background, enhancing the serene environment.

4.98 out of 5 average rating, 124 reviews

Vineyard views, hot tub, sauna, cinema

FamilyLocationHot tub

4.99 out of 5 average rating, 142 reviews

A covered hot tub is surrounded by curtain drapes and string lights, providing a cozy ambiance. The tub is filled with water that displays a soothing green hue, inviting relaxation in a tranquil outdoor setting.

Home in Geyserville

Updated 5 BR house w/ hot tub - walk to downtown!

LocationFamilyAir conditioning

4.99 out of 5 average rating, 135 reviews

Home in Guerneville

Redwood Retreat near Wineries and Sonoma Coast

LocationFamilyHot tub

4.96 out of 5 average rating, 133 reviews

Botany House Designer Home with Hot Tub

LocationFamilyLong stay

4.95 out of 5 average rating, 116 reviews

A bright kitchen features sleek white cabinetry and a spacious island with a light marble countertop. Pendant lights hang above the island, while large windows allow natural light to fill the space. Stainless steel appliances add a modern touch to the overall design.

Home in Windsor

Gourmet Kitchen in Wine Country w/Hot Tub + Office

FamilyLocationHot tub

4.95 out of 5 average rating, 174 reviews

A cozy living area features a light-colored sofa, complemented by a vibrant floral arrangement on a nearby table. Large windows offer broad views of the river and lush hills beyond, inviting natural light into the space.

Home in Jenner

Casa Panama: Relax in Luxury on the Sonoma Coast

FamilyValueComfort

4.95 out of 5 average rating, 184 reviews

A serene outdoor space features a circular seating area around a fire pit, with ocean views in the background as the sun sets. Lush trees provide a natural frame, while a hot tub is positioned nearby, creating an inviting atmosphere for relaxation.

Home in Bodega Bay

Ocean Front Paradise w Hot Tub&Fire Pit

LocationFamilyKitchen

4.97 out of 5 average rating, 116 reviews

An open-concept kitchen and dining area features a large wooden dining table and modern kitchen appliances. A spacious island with bar seating is included, and the bi-fold patio doors lead to a deck with lounge seating surrounded by greenery.

Home in Forestville

Russian River Luxury Escape | Private Hot Tub

FamilyLocationBathroom

House rentals with free parking

A well-appointed bedroom features a spacious bed with a light-colored upholstered headboard, draped in soft linens and a textured throw. Two nightstands flank the bed, each with a lamp and decorative items. Large windows allow natural light to illuminate the room, while soft curtains frame the view.

4.94 out of 5 average rating, 125 reviews

Centrally Located Modern Wine Country Home

FamilyLocationCleanliness

The kitchen features warm wooden cabinetry and an expansive central island. Stainless steel appliances include a refrigerator and microwave. Pendant lights illuminate the space, while natural light streams through a nearby window. Bar stools provide seating at the island, enhancing a functional cooking area.

5.0 out of 5 average rating, 199 reviews

Casa de Gamay - Your Home Away From Home

ValueLocationNearby

Two modern, white structures stand beneath a large green tree against a clear blue sky. The buildings feature large glass windows, allowing for natural light. The area is surrounded by open grass, contributing to a relaxed and spacious atmosphere.

4.85 out of 5 average rating, 158 reviews

Three-Building Healdsburg Homestead with Wine Barn

FamilyLocationWalkability

The bedroom features a spacious bed with white linens accentuated by a decorative pillow. A ceiling fan is present, and natural light enters through a window. Artwork adorns the walls, including a map and framed prints. A small desk and a television stand complete the space.

4.89 out of 5 average rating, 427 reviews

Wine Country Cottage in Healdsburg

LocationFamilyCleanliness

An outdoor seating area features two cushioned chairs and a wooden coffee table set atop a textured area rug. A vase with lemon branches and a wine bottle accompany glasses, inviting guests to enjoy leisurely moments in a peaceful garden setting.

4.98 out of 5 average rating, 111 reviews

Luxury wine country home 5 bedroom

FamilyLocationHeating

A light-filled living area features a sectional sofa, coffee table, and a flat-screen television mounted on the wall. Large windows provide sweeping views of the surrounding vineyards and natural light. A patterned area rug complements the wood flooring, enhancing the cozy atmosphere.

5.0 out of 5 average rating, 174 reviews

VINEYARD VIEW - Beautiful 3 bed/2 bath, Santa Rosa

LocationValueLaundry

4.94 out of 5 average rating, 107 reviews

A serene view of the landscape is captured, featuring tall oak and madrone trees with varying autumn colors. In the distance, gentle hills rise under a partly cloudy sky, providing a tranquil backdrop for the peaceful surroundings.

Home in Calistoga

Calistoga Hills Hideaway on 22 Acres

LocationFamilyAccess