Holiday rentals in St. Helena

4.99 out of 5 average rating, 434 reviews

Apartment in Napa

Silverado! Luxe 1BR King Suite This View! Balcony

Apartment with views! Top floor Silverado Resort true 1 bedroom (not studio), 1ba 676 sq. ft. w/ rare mountain views from the balcony, living and dining rooms. Wood burning fireplace. *Price includes tax. Walk to pool, market, dining, lounge at mansion. Newly remodeled, modern appliances, ready for your relaxation. Luxurious fine Italian linens from Frette. Just like a 5-star hotel. Roku streaming,Directv Hike or hang out in relaxing grounds! Solid surfaces, knobs sanitized during cleaning.

Guest house in St. Helena

4.96 out of 5 average rating, 120 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!

4.99 out of 5 average rating, 383 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.

4.87 out of 5 average rating, 242 reviews

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.

4.97 out of 5 average rating, 418 reviews

Cottage in Penngrove

Sonoma Mountain Artist's Retreat

Enjoy the perched feeling of Sonoma Mountain's setting with sweeping views and nature. The slightly tamed wilderness with an olive orchard and gardens sets the tone as you chill on the redwood deck. This is a studio cottage with expansive views to the western valley and Marin. Mount Tam appears through the windows from your super comfy bed. This is a beautiful and unique space adjacent to a mellow artist's studio. NOTE: Well behaved and Pre-Approved dogs available for a nightly fee.

4.99 out of 5 average rating, 110 reviews

Cottage in Calistoga

The Atlas Calistoga - Cottage #1

Make this sophisticated wine country cottage your personal Napa Valley hideaway. One of three luxury one-bedrooms on the historic Atlas Estate, the cottage blends a modern aesthetic with Zen-like tranquility and historic charm. This well-appointed property offers every comfort – from a fully stocked kitchenette to a cozy fireplace, and a sun-dappled outdoor seating area. Located in the heart of Calistoga, fine dining, shopping, spas and world-class wineries are at your doorstep!

4.97 out of 5 average rating, 109 reviews

Home in Calistoga

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.

4.96 out of 5 average rating, 886 reviews

Carriage House at Main Street Farmhouse!

Clean, comfortable, space on this Farmhouse property dating back to 1880. Enter exact number of guests for correct pricing $60 per person after 2. Studio with queen bed, full bathroom, kitchen with stove/oven, microwave, sauté pan, toaster, coffee and tea, dinette, tv area and IKEA queen sofa/sleeper. Beautiful patio with fire pit. Not suitable for children under the age of 12. Community fee (local lodging tax of 15%) is added to reservation when confirmed by guest.

4.88 out of 5 average rating, 278 reviews

Cabin in Calistoga

Wine Country Mountain Home

Whole house luxury for 2 in a Private forested location. 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% for travelers looking to work from home. Inquire with host.

4.98 out of 5 average rating, 192 reviews

Apartment in Napa

Luxe 1BR Condo Par Excellence at Silverado Resort

Experience the allure of Napa Valley in this sleek condo at Silverado Resort. Enjoy modern comforts and amenities in a stunning setting perfect for a romantic escape, a fun getaway with friends, or a peaceful retreat after wine tasting. Just 10 mins from downtown Napa, with wineries nearby and many more within a 15-min drive. Luxuriate in the modern design, a plush King bed with bamboo linens, and two electronic fireplaces for a cozy ambiance.

4.96 out of 5 average rating, 460 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 suite in St. Helena

4.91 out of 5 average rating, 347 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

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Popular amenities for St. Helena holiday rentals

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Pool

Free parking on premises

Air conditioning

Other great holiday rentals in St. Helena

4.95 out of 5 average rating, 19 reviews

Fairway Getaway

JamieRating, 5 stars4 weeks ago

Lisa was the best host, her place was exactly how she described and was in a beautiful location. She was very responsive to all and every question I had. We had a situation where we needed to change things around and she went above and beyond to accommodate me. She is by far the best host I have ever booked with and I definitely recommend her place. It was a great space for 4 girlfriends to have a long weekend in Napa. I will be back for sure. Thank you again Lisa for everything!

Superhost

Flat in Calistoga

4.85 out of 5 average rating, 48 reviews

Hidden Apartment at UpValley Inn & Hot Springs

AngelaRating, 5 stars1 month ago

Great hidden gem on the property of Up Valley Inn. Nicely decorated and a great option for anyone looking for an option with a kitchen. Nice easy and close walk to downtown Calistoga including restaurants, bars, shops and spas! Would absolutely recommend!

Superhost

Apartment in Napa

4.73 out of 5 average rating, 2,448 reviews

One Bedroom Cottage Along the Napa River

OmarRating, 5 stars2 weeks ago

Amazing village Definitely will come back

4.91 out of 5 average rating, 11 reviews

Flat in Angwin

Furnished Studio

StephenRating, 5 stars2 weeks ago

Michelle was great, very helpful and responsive throughout my stay. Offered suggestions for breakfast spots and was a great help throughout my stay.

5 out of 5 average rating, 15 reviews

Home in Sebastopol

Epic Views! Wine Country Retreat: Solar/EVCharger

RoxanneRating, 5 stars1 day ago

Pure magic. Dana’s one-of-a-kind Airbnb in Sebastopol is the epitome of luxury and serenity. From the moment we arrived, we were enveloped in a world of refined elegance and peaceful seclusion. Every inch of the home is masterfully curated with exquisite designer furniture, high-end finishes, and luxurious amenities that far surpass anything typically found in an Airbnb. The atmosphere is tranquil, sophisticated, and deeply restorative. The grounds are absolutely breathtaking—lush, expansive, and meticulously landscaped to create a true sanctuary. Whether lounging with a glass of wine at sunset or enjoying a quiet morning coffee surrounded by nature, every moment felt like a dream. Dana is a phenomenal host—gracious, intuitive, and incredibly accommodating. She anticipated every need, making our stay effortless and indulgent. This is not just a place to stay—it’s a destination for true relaxation and elevated living. Don’t hesitate- just book this sensational place!

5 out of 5 average rating, 9 reviews

Home in Glen Ellen

WolfPack-near Wineries & Morton’s Geothermal Pools

StacyRating, 5 stars1 week ago

What a hidden gem!! The area is so peaceful with deer and birds just outside your window. Decorated so nicely, full kitchen and comfortable beds. The pictures don’t do it justice. I highly recommend Melissa’s place for a beautiful stay.