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Vacation rentals in St. Helena

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Quick stats about vacation rentals in St. Helena

  • Total vacation rentals

    Explore 100 vacation rentals in St. Helena

  • Nightly prices starting at

    St. Helena vacation rentals start at G$12,546 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,450 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    90 of St. Helena vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across St. Helena rentals

  • 4.9 Average rating

    St. Helena stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in St. Helena

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
Aerial view of a serene property surrounded by lush greenery and landscaped gardens. Two distinct structures are visible, featuring modern architecture and a stone retaining wall. Tall cypress trees line the pathway, adding to the tranquil, private atmosphere.
Guesthouse in St. Helena
4.95 out of 5 average rating, 137 reviews

Romantic Napa Valley Cottage

Looking for the perfect getaway? This modern studio nestled among California oaks is serene, private and gorgeous. Just minutes from downtown St Helena, enjoy easy access to Napa's best wineries and restaurants. With over 375+ wineries, you'll never be bored! Relax on the huge deck outside your door in between your adventures or get the green thumb going in the garden with more than 1,000 trees, flowers, and shrubs. Ask about host's insider tips to get the most out of your stay in Napa Valley!

Top guest favorite
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.
Home in Calistoga
4.97 out of 5 average rating, 125 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!

Top guest favorite
A charming Victorian home with yellow siding is framed by lush greenery and seasonal trees. A welcoming porch is lined with white railings, leading to bright windows that invite natural light. A decorative archway of climbing plants enhances the home's exterior.
Home in Calistoga
4.96 out of 5 average rating, 238 reviews

Cedar Street Victorian

Turn of the century Victorian heritage home less than half a block walking distance to restaurants, wine tasting, shopping, spas and the year round Sat farmers market. You’ll love the house because of the comfy beds, the outdoor space, and the neighborhood. It is good for couples, solo adventurers, business travelers, and adult family functions. Pioneer park is right across the street. Every Thurs night in the summer months there are free concerts you can enjoy from the front porch.

Guest favorite
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.
Home in St. Helena
4.78 out of 5 average rating, 108 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.

Top guest favorite
A private patio features a swinging egg chair, capable of seating at least two people, surrounded by lush bamboo and a grassy area. Outdoor lights can be seen, complementing the serene atmosphere, while a pyramid heater provides warmth for cooler evenings.
Condo in Napa
4.99 out of 5 average rating, 140 reviews

Spacious&PeacefulOasis!Beautiful!PerfectlyLocated!

✨✨ Welcome to Your Modern Napa Stay! ✨✨ Discover the perfect blend of luxury and comfort in our stunning 2 bed, 2 bath spacious space. This contemporary retreat features stylish decor, an open-concept living space, ideal for relaxing after a day of exploring the beautiful wineries and vibrant culinary scene. Whether you're here for a romantic getaway, a trip with friends, or a family vacay, our modern Napa retreat offers everything you need for a memorable stay!

Top guest favorite
A light-filled living area features a cozy sofa adorned with decorative cushions and a glass coffee table. Soft curtains frame the sliding doors, which lead to an outdoor space. Minimalist decor and wooden furnishings complement the inviting atmosphere.
Apartment in Napa
4.97 out of 5 average rating, 321 reviews

Downtown Napa Unit B - Walk to Everything

Napa City Certified Vacation Rental Permit #VR16-0058, Napa Business License #26075 - Villa Murialdo in the Heart of Charming Napa, directly across from the the entrance to the Napa River Walk! Choosing the right accommodation in the heart of Napa means you are close to absolutely everything you want to experience during your stay. Villa Murialdo is within walking distance of world famous restaurants and a short drive from the renowned wineries.

Guest favorite
Aerial view of a modern farmhouse villa surrounded by lush, rolling hills. Vibrant flowering trees line the property, alongside a grassy landscape that slopes gently upward. The natural setting offers a sense of seclusion, with trees creating a backdrop against clear blue skies.
Villa in Santa Rosa
4.98 out of 5 average rating, 131 reviews

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.

Top guest favorite
The spacious bathroom features a modern dual-sink vanity with a large circular mirror above. A freestanding bathtub is positioned beside a natural light-filled window, with greenery adding a touch of nature. A glass shower enclosure is visible, complemented by stylish overhead lighting.
Apartment in Napa
4.97 out of 5 average rating, 609 reviews

A Private Guesthouse Studio – The Otter

the Otter studio - a peaceful standalone studio in the heart of Napa Valley wine country. The Otter Studio is less than one mile from Downtown Napa but far enough away from the hustle and bustle to provide a tranquil retreat while retaining every thoughtful amenity. Enjoy our cozy living space. We are legally permitted to rent to Napa Valley visitors. Ask about our other Napa listings if the dates here are booked.

Top guest favorite
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.
Home in Calistoga
4.97 out of 5 average rating, 394 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.

Top guest favorite
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.
Home in Napa
4.93 out of 5 average rating, 405 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

Superhost
A cozy bedroom features a spacious bed adorned with decorative pillows. Two armchairs are positioned near a window, offering a view of the greenery outside. Light-colored curtains frame the windows, enhancing the bright atmosphere while a bedside lamp provides soft illumination.
Home in Napa
4.87 out of 5 average rating, 134 reviews

perfect Vacation House & Napa

Enjoy everything in your holiday, with your family and friends needs ,this centrally located property It's very close, Downtown Napa Valley The house with two big bed room small living room and very good price for big family holidays in the Napa Valley,

Guest favorite
Condo in St. Helena
4.98 out of 5 average rating, 281 reviews

2 Bedroom Flat in Downtown St. Helena

Charming 2 bedroom condo in the heart of St. Helena. 5 minute walk to downtown shops, restaurants, and wine tasting. Steps away from walking path through 40 acre vineyard. Short drive to Calistoga, Yountville, and Napa. St. Helena STR Permit: STR25-011

Popular amenities for St. Helena vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

Stay near St. Helena's top sights

V. Sattui Winery

72 locals recommend

Culinary Institute of America-Greystone

44 locals recommend

Duckhorn Vineyards

30 locals recommend

Beringer Vineyards

28 locals recommend

Joseph Phelps Vineyards

25 locals recommend

Cameo Cinema

24 locals recommend

Other great vacation rentals in St. Helena

Guest favorite
Home in St. Helena
4.94 out of 5 average rating, 18 reviews

Luxury Napa Valley Estate Vineyard Views St Helena

Top guest favorite
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.
Home in St. Helena
5.0 out of 5 average rating, 32 reviews

Urban Retreat in the Heart of Napa Valley!

Guest favorite
Guesthouse in Calistoga
5.0 out of 5 average rating, 20 reviews

Downtown Calistoga Wine Country Getaway & Patio

Guest favorite
Villa in St. Helena
4.96 out of 5 average rating, 93 reviews

Boutique Compound on Vineyard, with Guest House

Guest favorite
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.
Home in St. Helena
4.97 out of 5 average rating, 35 reviews

Downtown St. Helena Vineyard Cottage

Top guest favorite
Condo in Napa
5.0 out of 5 average rating, 33 reviews

Remodeled Napa, CA Silverado Golf Course Condo

Guest favorite
Home in Calistoga
4.97 out of 5 average rating, 63 reviews

Vineyard View Home + Complimentary Wine Tasting

Top guest favorite
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.
Home in Calistoga
4.96 out of 5 average rating, 84 reviews

Calistoga Dream Inn

When is the best time to visit St. Helena?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$81,546 GYDG$81,546 GYDG$93,465 GYDG$99,110 GYDG$105,592 GYDG$86,565 GYDG$20,909 GYDG$20,909 GYDG$20,909 GYDG$23,418 GYDG$20,909 GYDG$83,637 GYD
Avg. temp10°C10°C11°C11°C12°C13°C14°C14°C15°C13°C12°C10°C

Frequently Asked Questions

  • What are the best places to stay in St. Helena?

    Many guests choose accommodations around Main Street for walkability to shops and dining, while stays near vineyard settings are often suggested for a more tranquil retreat. Family homes and guest cottages add variety in local neighborhoods.

  • What are the best things to do in St. Helena with kids?

    Children often enjoy local parks, hands-on workshops at art centers, or visiting family farms for seasonal outings. Ice cream shops and bakery stops along Main Street make for memorable treats.

  • What are some of the best things to do in St. Helena?

    Explore local wineries, stroll through historic Main Street shops, and discover art galleries around town. Outdoor enthusiasts can visit nearby hiking trails or picnic areas for scenic views.

  • How is the weather in St. Helena?

    St. Helena has cool, rainy winters averaging 44–56°F (7–13°C), and warm, dry summers with daytime highs around 51–66°F (11–19°C). Light layers and a rain jacket are useful, especially in the cooler months.

  • When is the best time to visit St. Helena?

    Late spring and early autumn are often recommended for mild temperatures and vineyard activities. Summer has lively energy and outdoor events, while winter is quieter with cooler, rainy days.

  • What are the best places to visit in St. Helena?

    Main Street is frequently suggested for its historic charm and variety of boutiques, galleries, and cafes. Visitors also explore local wineries and tranquil gardens around town.

  • What are some hiking trails in St. Helena?

    Hikers can explore tree-lined paths and gentle hillside trails around St. Helena, where oak woodlands and vineyard views meet. Guided nature walks or self-led routes near parks are frequently suggested.

  • What are some family activities we can do in St. Helena?

    Families frequently explore local parks, visit hands-on art spaces, or enjoy casual picnic spots. Some farms and nature centers in the area host family-friendly activities and seasonal events.

  • What are some of the best day trip ideas from St. Helena?

    Explore neighboring towns with additional wineries, local markets, or historic sites, or head to nearby state parks for hiking and nature activities. Art galleries and lakes also make for engaging outings.

  • Are there any pet friendly accommodations available in St. Helena?

    St. Helena has a selection of pet-friendly stays, including cottages and vacation rentals with outdoor spaces. Local parks nearby make it convenient to get outside with your dog.

  • What are some local tips for visiting St. Helena?

    Weekdays around Main Street are often quieter for strolling or wine tastings. Many shops and wineries encourage reservations, and a sun hat comes in handy during warm months.

  • What is St. Helena known for?

    St. Helena is known for its scenic vineyards, locally driven cuisine, and charming small-town atmosphere. The community has a strong tradition of winemaking and farm-to-table dining.

  • What are the best hidden gems to explore in St. Helena?

    Wander through small family-owned vineyards or stop by boutique tasting rooms for a laid-back experience. Art studios and locally owned cafés around town often surprise visitors with thoughtful details.

  • What are the best foods to try in St. Helena?

    St. Helena has farm-fresh fare, wood-fired pizzas, artisanal cheeses, and locally grown produce. Meals often feature seasonal ingredients paired with wines from nearby vineyards.

  • What should I bring for a trip to St. Helena?

    Pack light layers, comfortable shoes for walking or vineyard tours, and a hat for sunny days. A rain jacket can be helpful in winter and early spring.

  • What is the nightlife in St. Helena like?

    Evenings in St. Helena tend to be relaxed, with wine bars, cozy lounges, and restaurants offering seasonal menus. Occasional live music and local gatherings add warmth to the nighttime atmosphere.

  • What are the most popular events or festivals in St. Helena?

    St. Helena’s calendar often features wine harvest celebrations in early autumn, spring food festivals, and community art events. Wine and culinary gatherings around harvest time are frequently suggested.

  • Are there family friendly vacation rentals in St. Helena?

    Family-friendly vacation rentals are available throughout St. Helena, including houses with kitchens, patios, and outdoor spaces. Many are near parks, playgrounds, or local shops for convenience.

Destinations to explore