Holiday houses in St. Helena

4.99 out of 5 average rating, 503 reviews

Silverado! Luxe King Suite Mountain View Balcony

Apartment with views! Top floor Silverado Resort true 1 bedroom (not studio), 1ba 676 sq. ft. w/ rare mountain views from balcony, living and dining rooms. Wood burning fireplace. *Price incl tax. Walk to pool, market, dining, lounge at mansion. Modern appliances, ready for your relaxation. Luxurious fine Italian linens from Frette on King bed. Just like a 5-star hotel. Roku streaming,Directv Hang out or walk in relaxing grounds! La-Z-Boy queen sofabed, Aug 2025. Free L2 EV chargers nearby.

4.95 out of 5 average rating, 134 reviews

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

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!

4.96 out of 5 average rating, 203 reviews

A serene courtyard features a circular firepit surrounded by four wicker chairs, inviting relaxation. Sunlight filters through the trees, creating a warm ambiance. Lush greenery and a vineyard view extend beyond the enclosure, enhancing the tranquil outdoor space.

Guest suite in Napa

Sherrie's Vineyard View Retreat-Pool, Spa, N.Napa

Enjoy our vineyard view and a glass of wine by the firepit! Relax in our ONE BEDROOM SUITE, ON THE LOWER LEVEL OF OUR TRI-LEVEL HOME. Conveniently located in N. Napa, we're near Alston Park for hiking, wineries, places to eat & shop. Enjoy a fresh-baked BREAKFAST, a dip in the pool (heated mid-June to Sept), spa (year-round) & many places for relaxing. Our suite is well appointed with a comfortable bed, fine linens, duvet, robes & slippers. DRIVING SERVICES may be added to enhance your tours.

A modern living space is displayed with a sectional sofa adorned with decorative pillows. A rectangular coffee table is centered on a subtle area rug, while a round mirror adds depth to the room. The open layout connects to a kitchen area featuring sleek cabinetry and bar seating.

4.99 out of 5 average rating, 127 reviews

Serene 1 BR Condo at Silverado Resort

Calming, relaxing, and stylish, this newly-remodeled 2nd floor condo at Silverado Resort is modern, serene, and peaceful. It’s perfect for a couple's celebration, a special birthday, or a quiet place to stay after enjoying one of the many events hosted at this famed property! Blending urban sophistication with Wine Country charm, this exquisite condo features upscale amenities, 100% bamboo linens, a posh sleeper sofa, two fireplaces, and a premium King size mattress for next level sleep bliss.

4.99 out of 5 average rating, 421 reviews

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

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.

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.

4.96 out of 5 average rating, 111 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!

4.95 out of 5 average rating, 120 reviews

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

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.

4.85 out of 5 average rating, 251 reviews

A light yellow house features a welcoming front porch with white railings and a staircase leading to the entrance. Windows along the upper level allow natural light, and the well-kept yard includes shrubs. A mailbox is positioned at the foot of the stairs.

Home in St. Helena

The Dollhouse in Saint Helena

Charming remodeled Victorian 2 bdrm/2 bath - Light & spacious home. WD- Fireplace- Walking distance to downtown St. Helena,, several wineries and vineyards. 3 min walk to Farmstead, Charter Oak, Gott's and NV Health Spa. Plenty of HOT water in the bathrooms. Modern fully stocked kitchen/All linens and towels provided. Upstairs: Living Room/Dining Room/Kitchen/Guest Bdrm/Full Bath Downstairs: Den with Smart TV/Master Suite Great backyard for dining. Legal short term rental permit.

4.89 out of 5 average rating, 295 reviews

The entrance features a wooden deck with steps leading up to a door, surrounded by lush greenery. Decorative metal accents and potted plants add character, while wooden double doors below exhibit rustic charm. The overall setting is inviting and blends harmoniously with the natural surroundings.

Cabin in Calistoga

Wine Country Mountain Home

Whole house wine country luxury for 2 in a Private and secluded forested location. Hidden ‘Cabin in the Woods’ vibe. Starlink WiFi, Forest at your front door. Clean and Comfortable vintage cabin In the mountains. Mid way between Napa and Sonoma valleys: 7 miles to Calistoga; 10 miles to Santa Rosa. NO cleaning fee at check out. Self-check-in with lock box. Professionally cleaned and sanitized before all check ins. Monthly discounts of 50%, weekly discounts 25%

4.98 out of 5 average rating, 355 reviews

A cozy living area features a comfortable gray sofa adorned with patterned cushions. A light marble coffee table sits in front of the sofa, while two modern lamps provide illumination. A piece of abstract wall art adds a touch of color above the seating area.

Apartment in Napa Abajo

Downtown Napa Unit C - 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.

4.97 out of 5 average rating, 544 reviews

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

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 suite in St. Helena

A private outdoor space is shown, featuring a red seating area with cushions and a small wooden table. The area is framed by a pergola adorned with greenery, enhancing the inviting atmosphere. Natural light is poured in through the double glass doors, which lead into the apartment.

4.91 out of 5 average rating, 363 reviews

One Bedroom Wine Country Getaway

Light-filled one beroom lower apartment in the historic west side of St. Helena walking distance to downtown shops, dining and wineries! A short walk 7 minute walk to downtown St. Helena, restaurants and wineries. Owners live in the upstairs unit and are out-of-sight but more than happy to help with local tips and recommendations! St Helena STR Permit: PL19-035

Popular amenities for St. Helena holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in St. Helena

4.96 out of 5 average rating, 81 reviews

Home in Healdsburg

Wine Country Retreat • Fire Pit • 2-for-1 Tastings

Superhost

A row of charming cottages is lined along a walkable path, featuring varied exterior colors including blue, yellow, and red. Each unit has large windows and decorative gables, surrounded by neatly trimmed hedges and lush green trees, enhancing the inviting neighborhood atmosphere.

Condo in Napa

4.73 out of 5 average rating, 2,607 reviews

One Bedroom Cottage Along the Napa River

4.83 out of 5 average rating, 6 reviews

Silverado Retreat- Your Napa Sanctuary

5 out of 5 average rating, 9 reviews

Home in Jenner

Pacific Sunset is Waiting for You!

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.

4.98 out of 5 average rating, 64 reviews

Calistoga Dream Inn

5 out of 5 average rating, 6 reviews

Bungalow A

A living room area features a cozy seating arrangement, including a sectional sofa, armchairs, and ottomans. A fireplace serves as a focal point beneath a wall-mounted television. Natural light enters through the window, illuminating the neutral-colored walls and soft furnishings.

4.97 out of 5 average rating, 198 reviews

Elegant Napa Escape

A chalet-style home is set within a natural landscape, showcasing a spacious deck that wraps around the structure. Stone pathways lead to lush greenery and decorative plants, while outdoor seating is visible in front of the home. Large windows reflect the surrounding trees.