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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 $84 CAD 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 and 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

  • Wifi availability

    90 of St. Helena vacation rentals include wifi 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 favourite
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!

Guest favourite
An open-plan living and dining area is illuminated by natural light from large glass doors. A comfortable sofa and armchair are arranged around a decorative coffee table. A dining table for four is set with dishware, while a modern artwork adds color to the wall.
Condo in Napa
4.96 out of 5 average rating, 233 reviews

Gorgeous condo at Silverado Country Club

This beautiful condo at Silverado Country Club is your dream Wine Country Escape. Surrounded by beautiful trees, it's the perfect location for a relaxing stay. The condo features an open plan living room and dining area, a kitchen and two large bedroom suites, one with a king and the second with a queen size bed. Each bedroom has a fully remodeled bathroom with walk in shower. The spacious deck offers a BBQ grill and a picturesque view of the golf course, nestled among beautiful oak trees.

Top guest favourite
The living room features a comfortable gray sofa and two elegant armchairs surrounding a wooden coffee table. Natural light fills the space through large windows. A dining area is visible through an open doorway, with a plush bed and decorative wall art adding to the atmosphere.
Apartment in Napa
4.99 out of 5 average rating, 444 reviews

Mendez on Main #2 / King Bed/1 bath Walk to town

Indulge in Napa's finest restaurants, wine tasting, and nightlife from our beautifully restored and remodeled apartment in our Victorian home, just a 10-minute stroll from downtown. Our apartment is fully equipped with all the amenities you'd expect, (*No stove) creating a comfortable space for your stay. For the peace and relaxation of all guests, please note that we do not allow pets or children under 12. You can book with confidence knowing that we have a Use Permit from the City of Napa.

Guest favourite
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, 120 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 favourite
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
4.97 out of 5 average rating, 234 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 favourite
A wooden bridge connects the ground to a treehouse elevated among tall trees. The treehouse features large windows and a circular design, surrounded by lush greenery. A sturdy netting lines the sides of the walkway, ensuring safety while traversing to this unique retreat.
Treehouse in Bodega Bay
4.95 out of 5 average rating, 226 reviews

Eagle's Nest Treehouse Farm Stay

Eagle's Nest Treehouse Farm Stay is a tranquil, secluded, luxurious, romantic wilderness experience in a private forest on a 400 acre working ranch. Thirty feet above the forest floor you are nestled in a gorgeous, well-appointed suite of 1,000 year old polished redwood, with bathroom and amazing copper/glass forest-view shower. Explore hiking trails through the forest and learn about ranch operations (Highland cattle, goats and ducks). See guest comments in the space description.

Guest favourite
A charming cottage exterior is framed by lush greenery and mature trees. The white facade is complemented by light blue shutters and a dark front door, while two wicker chairs are placed on a semi-private porch, inviting relaxation among the serene environment.
Cottage in Calistoga
4.95 out of 5 average rating, 157 reviews

Luxury Cottage in Downtown Calistoga - Accessible

Escape to Wine Country– Your Cozy Napa Valley Retreat Tucked in charming Calistoga, our private cottages offer the perfect blend of comfort and relaxation. Enjoy luxury amenities like plush beds, fireplaces, en-suite bathroom with 2 person soaking tub, plus delightful morning treats with locally roasted coffee, pastries, and fresh fruit. Borrow a complimentary bike to explore nearby wineries or stop by our on-site office (9 AM-5PM) for wine or local tips. Pet-friendly options available.

Top guest favourite
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.
Home in Calistoga
4.98 out of 5 average rating, 146 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.

Top guest favourite
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, 128 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!

Guest favourite
A rustic cabin is nestled among towering redwood trees, featuring wooden shingles and large windows. A wooden deck, adorned with string lights, enhances the inviting exterior, while the natural landscape provides a serene backdrop. A gravel path leads to the entrance.
Cabin in Occidental
4.97 out of 5 average rating, 624 reviews

Rustic Yet Luxurious Cabin in the Redwoods

This rustic yet luxurious cabin is the perfect place to unplug. Walk through the woods, relax by a fire, and enjoy the food and wine of the Russian River Valley. 10 minutes from the beach. Minutes from Occidental, Graton, Forestville, and Guerneville. House has a full bathroom, bedroom downstairs with a Cal King bed and one upstairs with two twin beds. 5 acres in the redwoods, trampoline, fire pit area, high-speed Internet.

Top guest favourite
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, 586 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.

Guest favourite
Home in St. Helena
4.92 out of 5 average rating, 12 reviews

Luxury Napa Valley Estate Vineyard Views St Helena

Architectural Napa Valley estate in the heart of St Helena with panoramic vineyard views, soaring cathedral ceilings and steel frame glass walls. Three stunning bedrooms including two open loft suites, spa caliber bath, chef kitchen with professional gas range, fire pit terrace with vineyard views and Peloton style bike. Minutes from Beringer, Hall, Duckhorn, Frank Family and Stag's Leap.

Popular amenities for St. Helena vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near St. Helena's top sights

V. Sattui Winery

72 locals recommend

Culinary Institute of America-Greystone

44 locals recommend

Charles Krug Winery

16 locals recommend

Other great vacation rentals in St. Helena

Guest favourite
Guesthouse in Calistoga
5 out of 5 average rating, 12 reviews

Downtown Calistoga Wine Country Getaway & Patio

Top guest favourite
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
5 out of 5 average rating, 32 reviews

Downtown St. Helena Vineyard Cottage

Top guest favourite
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.
Home in Calistoga
5 out of 5 average rating, 36 reviews

Wine Country Retreat with Vineyard Views

Top guest favourite
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 out of 5 average rating, 31 reviews

Urban Retreat in the Heart of Napa Valley!

Top guest favourite
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.
Home in St. Helena
5 out of 5 average rating, 23 reviews

Charming Wine Country cottage close to downtown

Top guest favourite
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
4.97 out of 5 average rating, 79 reviews

Calistoga Dream Inn

Top guest favourite
Condo in Napa
4.9 out of 5 average rating, 20 reviews

Silverado Retreat- Your Napa Sanctuary

Top guest favourite
Home in Calistoga
4.98 out of 5 average rating, 49 reviews

Vineyard View Home + Complimentary Wine Tasting

When is the best time to visit St. Helena?

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Avg. price$547 CAD$547 CAD$627 CAD$140 CAD$140 CAD$140 CAD$140 CAD$140 CAD$140 CAD$157 CAD$140 CAD$561 CAD
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

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