House holiday rentals in St. Helena

5.0 out of 5 average rating, 123 reviews

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.

Home in Healdsburg

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!

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, 124 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!

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, 211 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.✨

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.

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.

4.97 out of 5 average rating, 241 reviews

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.

Home in Santa Rosa

Elegant & Spacious Luxury Wine Country Estate

The perfect place for your group to stay in Wine Country! Featuring two large entertaining areas and an additional dining room, this is a great place for fun and relaxation! Play ping pong, pool or poker in our game room, or dine on our spacious patio under the pergola! Relax and soak in our hot tub and enjoy the zen gardens and tranquil water feature, or sip on a glass of wine by the outdoor fire pit. Close to the Sonoma County Airport, wineries, and world-class dining. Welcome home!

A two-story light green house is set amidst lush landscaping, featuring well-maintained lawns and flowering bushes. A covered porch is visible on the upper floor, and trees provide shade around the property. The clear blue sky adds to the inviting outdoor ambiance.

4.94 out of 5 average rating, 169 reviews

Come and Visit the Valley Sleeps 4 to 8 Guests

Great place for friends and family to gather. Come and see what the valley has to offer. Many wineries, fine dining and great shopping. This home is a beautifully remodeled 4 bedroom 3 bath home (2 of the bedrooms are mater suits). Includes eat in chefs kitchen, sun room / private office, living room, laundry room. Backyard landscaped to feel like a park setting. Large outdoor patio with dining table and seating for 8, Gazebo with outdoor lighting and BBQ Permit #VR17-0060

4.78 out of 5 average rating, 107 reviews

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

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.

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, 151 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.

The exterior of the Mediterranean cottage showcases a terracotta tile roof and white stucco walls. Lush greenery and colorful flowering plants surround the home, enhancing its inviting curb appeal. Large arched windows provide a glimpse of the cozy interior, framed by mature trees.

4.94 out of 5 average rating, 339 reviews

F.J. Massa House

Named in honor of an Italian immigrant who settled in Napa in the early 1900’s to grow vegetables for his new-found community. Frank Massa built this mediterranean cottage as a wedding gift for his wife-to-be in 1930. The two bedroom, one bathroom cottage is listed on the historic register and fully restored to its original elegance & appointed with original furnishing and fixtures from the 1930's. City of Napa Vacation Rental Permit #VR09-0049. Business Lic # 27744

A vibrant hot air balloon floats above a vineyard, showcasing a striking yellow and black pattern. The landscape features well-manicured lawns and shrubs, with a chain-link fence partially enhancing the view of the mountains in the distance.

4.98 out of 5 average rating, 423 reviews

Vineyard House In The Heart Of Napa Valley

La Casita Megandina will create a memorable vacation experience for you and your family. Our house is centrally located in the heart of the Napa Valley only minutes from wineries and world famous restaurants. Our slogan is “Come Experience the Napa Valley Lifestyle at its Finest”. The house borders on a vineyard which give you an amazing view in a quiet neighborhood. Guests from around the world have enjoyed staying with us and we would like to share our house with you.

4.95 out of 5 average rating, 509 reviews

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.

Home in Sonoma

Zen House Sonoma

This is a tranquil retreat in a magnificent setting, surrounded by a creek, and by meadows and woodlands. You will love the way natural light floods the house, and the feeling of being out in nature even when you are inside. The house is open and spacious with outside decks for entertaining, and for enjoying the fresh air and the peaceful quiet. Set for 4 guests but can easily accommodate 6-8. There is an extra $100 nightly per-person charge for parties over 4.

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.