House holiday rentals in St. Helena

4.99 out of 5 average rating, 303 reviews

The spacious outdoor deck is illuminated in the evening glow, featuring multiple seating areas, a dining table, and a hot tub. Large glass doors provide a view into the inviting interior, framed by tall redwood trees, creating a serene ambiance.

Home in Glen Ellen

Quiet Wine County Retreat with Bocce and Hot tub!

Central wine country location Close to wineries, tasting rooms, gourmet market, french bakery & restaurants New luxury 3-BR, 2.5 bath Hot tub & bocce ball We can host 5 adults + 2-3 kids Quiet spacious home nestled in the redwoods on 1/2 acre Complimentary pastries from local bakery Linens, towels, spa robes & toiletries provided Complimentary coffee, tea & sugar Huge outdoor decks with 3 seating areas, dining table, fire-pit Corn-hole, giant jenga & board games Kids’ books, games & baby items

LocationFamilyBarbecue

4.97 out of 5 average rating, 126 reviews

A comfortable living room is displayed, featuring a leather sectional couch complemented by decorative cushions. A television is positioned nearby, with a stylish wooden coffee table in front. Warm light filters through a large window, illuminating the open kitchen area with modern appliances.

Home in Glen Ellen

Fireside Sips & Oak Dreams in Sonoma Valley

Ultimate wine country escape! Stylish 3-bedroom, 1-bathroom oasis nestled in serene Sonoma Valley. Charming getaway features an equipped kitchen, inviting outdoor patios, BBQ grill, outdoor games, and cozy fire pit, perfect for enjoying stunning wooded backdrop. Unwind on the Peloton bike or indulge in board games. Ideal destination! Downtown Glen Ellen and Kenwood wineries are just a five-minute drive away. A perfect balance of seclusion and convenience await you. Pets are allowed, with fee.

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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 out of 5 average rating, 119 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!

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A cozy living area features a modern yellow armchair positioned near a stone fireplace, which holds a lively flame. A round coffee table with an intricate design sits in front, while large sliding glass doors showcase views of the outdoor deck area.

4.97 out of 5 average rating, 157 reviews

Stunning Sonoma | HOT TUB | Game Room | Sleeps 6

Enjoy stunning views of Sonoma! Welcome to Sonoma Vista, minutes from renowned wineries and Downtown Sonoma. Perfect perch for families, couples! Nestled in oak-studded hills, this modern haven boasts three bedrooms, two sleek bathrooms with heated floors, and remote-work-friendly desks. Indulge in a mid-century bar, chef's kitchen, and a jaw-dropping game room. Outside, a vast deck with dining, fire pit, and lounge seating awaits. Immerse yourself in wine country luxury at Sonoma Vista!

ValueFamilySleep quality

A craftsman cottage is set atop a gentle hill, featuring a welcoming porch framed by blue trim. Low stone steps lead to the entrance, and the pathway is suitable for vehicle access. Lush greenery surrounds the structure, enhancing its peaceful country setting.

4.91 out of 5 average rating, 276 reviews

Cozy Craftsman Cottage

Charming, peaceful one bedroom craftsman cottage on natural 60 acre property on a country road. Vaulted ceilings, wide plank hardwood floors, wood burning stove and full kitchen. The lake is a 5 minute walk- beautiful to enjoy but is not for swimming. Myself and the property owner do live on property. 15 minutes from downtown Calistoga, 30 from downtown Healdsburg and 30 minutes from Santa Rosa. Your four legged friends are welcome for an additional $50 pet fee which I will send separately

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A modern living area features a large dark green sofa complemented by a cozy white chair and a stylish coffee table. Natural light streams through multiple windows, illuminating a patterned area rug. A dining area and kitchen are visible in the background.

4.97 out of 5 average rating, 122 reviews

Calistoga Tejas Trails

Welcome to Tejas Trails, your country getaway nestled in Calistoga's mountain vistas, just 10 minutes from downtown. This new home (2023) is easy to share with friends or family. Enjoy refreshing mountain sunrises, dinners on the huge deck, watch sunsets sipping wine by the firepit, swing under a large oak tree, and take tranquil walks on the country road. This is the perfect place to leave the hustle and bustle behind, while still minutes from Napa Valley’s finest restaurants and wineries!

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A spacious living area features a modern wall-mounted television and comfortable seating arrangements. A stylish coffee table sits at the center, surrounded by a large area rug. Decorative elements include a plant and artwork, adding a subtle touch to the neutral color palette.

4.96 out of 5 average rating, 210 reviews

A Wine Travelers Dream in the Heart of Napa Valley

✨Welcome to our beautiful Napa Valley home, perfectly situated between the vibrant energy of downtown and the breathtaking beauty of the Valley. 6 minutes to downtown Napa, 5 minutes to Silverado trail, 20 minutes to Sonoma. Indulge in the world-class restaurants, vibrant nightlife of downtown, or venture into the valley to explore the rolling hills and picturesque landscapes that have made this region famous. After a day of adventure, retreat to our ample space to rewind and rejuvenate.✨

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The charming cottage features a light-colored exterior with decorative trim. A welcoming front porch is adorned with planters, while a large window allows natural light to fill the space. Lush greenery surrounds the home, providing a serene atmosphere.

4.78 out of 5 average rating, 107 reviews

Heart of Napa Valley - 2BR Retreat

City of St. Helena Permit #2012-27 Welcome to our charming two bedroom cottage in St. Helena, the heart of the Napa Valley. Our home is just steps from downtown restaurants, grocery store, shops, movie theatre, and wineries. Enjoy all the famed Napa Valley wine country has to offer. Choose to spend the day tasting at some of the world's premier wineries or visit the shops of St. Helena, Yountville, Calistoga and Napa. You may even want to visit the Outlet Stores in Napa.

ValueFamilyHeating

A charming exterior view of Casa LaBloom features a welcoming porch surrounded by lush greenery and palms. The front yard is landscaped with stone pathways and a small birdbath, creating a tranquil atmosphere. The house stands two stories, with a light-colored facade and inviting outdoor spaces.

4.98 out of 5 average rating, 149 reviews

Charming Home Just Steps From Wine & Hot Springs!

An oasis just 2 blocks from downtown Calistoga's tasting rooms, restaurants, hot springs, spas & shopping, Casa LaBloom is a charming home waiting for you to unWINE & relax. Enjoy a cup of perfect home made espresso on the front porch, or lunch under the palms and watch the world go by. Rather taste wine? There are 5 tasting rooms within 2 blocks - no need to drive! Casa LaBloom is the perfect cozy space for a family, or for couples on a secluded wine country get-away.

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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 out of 5 average rating, 263 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!

LocationFamilyIndoor spaces

The exterior features a bright green front door framed by contrasting black trim. Two large windows with decorative wooden accents are present beside the door. A wooden deck extends in front, providing accessibility and a welcoming entryway.

4.97 out of 5 average rating, 386 reviews

Vineyard Farmhouse w/ Pool & Mt. Helena Views

Private vineyard farmhouse with brand-new pool and panoramic Mt. Helena views. Set among the vines just 15 minutes from Calistoga, this recently styled retreat blends wine country charm with modern comfort. Unwind poolside by day, gather under the globe lights at night, and experience Napa Valley from your own secluded perch.

LocationFamilyCheck-in

An open living space features a cozy seating arrangement with gray sofas and a coffee table. A modern chandelier provides soft lighting above, while a dining area with a large table and chairs is visible through a wide doorway. Warm hardwood flooring complements the bright atmosphere.

4.93 out of 5 average rating, 398 reviews

Casita Rosa - Luxury in Downtown Napa

Casita Rosa is a two bedroom home located in historic downtown Napa. This charming, 1600 sq. foot home was built in 1927, and is a Spanish-style bungalow with lots of windows and beautiful light. This high spec, 2 bedroom/ 2 bathroom fully equipped home is located in a quiet residential area. City License VR19-0003

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Popular amenities for St. Helena house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A modern home is showcased with large sliding glass doors that open to a spacious wooden deck. The inviting heated pool features a gentle curve, with sun loungers placed nearby. Lush greenery surrounds the property, enhancing the tranquil outdoor setting.

4.95 out of 5 average rating, 546 reviews

Designer Sonoma Getaway with Pool, Hot Tub & Bocce

LocationFamilyView

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.

4.92 out of 5 average rating, 132 reviews

Vineyard Vista, Modern Farmhouse Cottage with Pool

LocationValueAir conditioning

4.83 out of 5 average rating, 120 reviews

The Elm House: Private Pool, Hot Tub, Napa Getaway

FamilyValueBackyard

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, 108 reviews

Wine Country Villa Heated Pool Hot Tub Upper Level

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The outdoor space features a gazebo with a fire pit, surrounded by comfortable seating. Lounge chairs are positioned near an unheated pool, and a dining table with seating is visible in the background, creating a welcoming atmosphere for relaxation and gatherings.

4.93 out of 5 average rating, 186 reviews

Wine Country Escape: Pool & Hot Tub. Fast WiFi

LocationFamilyIndoor spaces

4.98 out of 5 average rating, 133 reviews

Wine Country Retreat- Privacy-Spa/Pool/Games

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A modern kitchen features a spacious island with three woven bar stools. Hexagon-tiled walls in a soothing grey tone complement open shelving displaying dishware. Large windows allow natural light to fill the space, with greenery visible outside.

4.96 out of 5 average rating, 125 reviews

Modern wine country stunner with pool & pickleball

LocationValueTV

4.96 out of 5 average rating, 113 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

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Weekly house rentals

5 out of 5 average rating, 121 reviews

Home in Sebastopol

Pixel Place - A Private Arcade + Outdoor Sanctuary

ValueFamilyQuiet

4.94 out of 5 average rating, 417 reviews

Home in Kenwood

Wine Country Cottage

ValueFamilyHospitality

A charming yellow cottage with dark shutters and a bright red front door is presented. A stone pathway leads to the entrance, surrounded by well-maintained shrubs and greenery. Tall trees provide shade in the yard, enhancing the inviting exterior.

4.9 out of 5 average rating, 300 reviews

Yellow House w/ Hot Tub~ Walk to Oxbow & Downtown!

LocationFamilyView

4.98 out of 5 average rating, 183 reviews

Wake Up at Your Own Private Vineyard - Healdsburg

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4.93 out of 5 average rating, 15 reviews

Luxury Napa Valley Estate Vineyard Views St Helena

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A classic white house with a welcoming front porch is framed by lush greenery and mature gardens. The well-maintained pathway leads to grand double doors, inviting guests into a historic home rich in character and charm.

4.97 out of 5 average rating, 345 reviews

Stoddard House

ValueFamilyHospitality

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, 238 reviews

Elegant & Spacious Luxury Wine Country Estate

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A spacious retreat is nestled among greenery, featuring a stone pathway leading to the entrance. Solar panels adorn the roof, and soft lighting highlights the outdoor seating area. Surrounding gardens display a variety of plants, adding to the tranquil outdoor setting.

4.95 out of 5 average rating, 506 reviews

Zen House Sonoma

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Private house rentals

4.91 out of 5 average rating, 11 reviews

Modern Napa Escape | Minutes to Downtown Napa

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A charming cottage exterior showcases a light-colored façade contrasted by dark window frames and a blue door. Potted plants adorn the entrance, and a pathway leads to the door, surrounded by gravel and landscaped areas. Vineyards are visible in the background under a clear blue sky.

4.97 out of 5 average rating, 34 reviews

Downtown St. Helena Vineyard Cottage

LocationViewCheck-in

A spacious living area is highlighted by a stone fireplace, surrounded by comfortable seating and natural light. A dining area is visible in the background, complemented by large windows showcasing outdoor views. Neutral decor elements and a textured rug add warmth to the space.

5 out of 5 average rating, 37 reviews

Wine Country Retreat with Vineyard Views

LocationFamilyAir conditioning

A two-story home features a warm-toned exterior with a mix of stucco and stone accents. Large windows are adorned with grilles, allowing natural light to illuminate the interior. The landscaped front yard includes a variety of plants and a small tree, enhancing the inviting curb appeal.

5 out of 5 average rating, 31 reviews

Urban Retreat in the Heart of Napa Valley!

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Superhost

5 out of 5 average rating, 3 reviews

Napa Valley Escape with View & Jacuzzi / one month

LocationHospitalityCleanliness

The charming cottage features a welcoming front porch with a red door, surrounded by well-maintained gardens. Stone pathway leads to the entrance, with vibrant plants and gravel landscaping enhancing the outdoor space. Mature trees and vineyards are visible in the backdrop.

5 out of 5 average rating, 24 reviews

Charming Wine Country cottage close to downtown

FamilyLocationView

The classic farmhouse is surrounded by lush greenery, illuminated by soft outdoor lighting at dusk. Steps lead to a welcoming entrance, and a wrap-around porch is visible, enhancing the connection between indoor and outdoor spaces.

4.93 out of 5 average rating, 68 reviews

Napa Vineyard Farmhouse • Garden Estate

FamilyValueHospitality

The charming exterior of The Calistoga Dream Inn features a light yellow facade with purple accents. A welcoming porch area is highlighted, while the well-manicured lawn and pathway lead to the entrance. Natural greenery is visible surrounding the property.