Guesthouse holiday rentals in Wine Country

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Top-rated Guesthouses in Wine Country

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Top Guest favourite
A serene sleeping area is displayed, featuring a spacious bed adorned with soft linens and surrounded by natural light from large windows. A wooden table and chair provide a cozy setting, while decorative shoji screens and wood accents enhance the tranquil ambiance.
Guesthouse in Stinson Beach
4.98 out of 5 average rating, 266 reviews

Beach View at the Bird’s Nest Bungalow

Relaxing refuge set on a lush hillside in the quiet seaside town of Stinson Beach. Feel transported by the Asian inspired design and tranquil outdoor shower and soaking tub. Indulge in treetop ocean views from the comfort of a queen bed, and watch the sun set from the privacy of a wooden deck. Walk only five minutes to three miles of perfect beach. It's worth the journey down through the trees on uneven stone stairs and very steep wooden stairs to find yourself transported away from it all. A comfortable queen bed with plenty of pillows affords the perfect sitting spot to look out through the branches of the treetops at the ocean. The small kitchen area has all you need for simple cooking. You'll find extra blankets in the closet behind an antique Japanese room screen while the new handcrafted shoji screen conceals the toilet and bathroom sink. The outside shower is exhilarating (and for the adventurous in the rain and winter) while the soaking tub is beyond relaxing while looking at the ocean watching the sky change colors at sunset. Ahhhhh. Good WiFi, flashlights for night walking, aromatherapy for fully relaxing, eye masks for sleeping in! I like to give my guests total privacy, but I’m always available if needed. ( text is easiest) Stinson Beach is a quiet seaside town popular for its calm surf, smooth sand, and miles of mountain trails. The beach bungalow set on the hillside with wooden and stone stairs to arrive. Worth the trek, but if you have a bad knee, a tricky ankle or a hitch in your get-along, this is not the property for you. A car is recommended for day trips to Muir Woods, the Point Reyes National Seashore, Mt Tamalpais, a ferry ride to San Francisco and shopping in Sausalito. The Marin Airporter will get you from SFO to Mill Valley and then you can hop on the Stage Coach to town. (See Marin Transit Website). The Stage will take you in and around Marin County. However the best way to get around our small beach town is to park the car and walk. Our tiny town has three restaurants, one with fresh baked bread and take out, a library, bookstore , surf shop, kayak and surf rental shop, photography gallery, upcycled denim and hand dyed clothing shop, art galleries, jewelry, flower shop, and more. The Stinson Beach Market has all you'll need for a weekend getaway. You'll want to take a long or short hike on the beautifully maintained hiking trails of the Matt Davis or Steep Ravine and stroll the three miles of perfect sand of one of the best beaches in Northern California. You can surf, boogie board, paddle board, kite sail, or just plain put your feet in the water and marvel at the wonder of the ocean. Whether it's mountain or sea it's all about nature here in our coastal town. Guests must be realistic about climbing stairs. If you have a trick knee, an ankle that aches, or a hitch in your get-along, this is not the place you'll want to be.

Top Guest favourite
A spacious deck features wooden lounge chairs arranged for relaxation, overlooking the ocean. Glass railings provide an unobstructed view of Black Sands Beach and the surrounding cliffs. Natural light from the horizon casts a soft glow, enhancing the tranquil scene.
Guesthouse in Whitethorn
4.99 out of 5 average rating, 126 reviews

Mermaids View Breathtaking Ocean View-Pet Friendly

Take it easy at this unique and tranquil getaway overlooking the beautiful Black Sands Beach. The bottom level of the house is on the cliffs edge so you will have a Birds Eye view of all the whale activity and people watching on the beach. The large deck has glass railing which makes it completely unobstructed. There are no neighbors directly on either side so it is very quiet and private. Newly renovated small-scale kitchen & living room. Just a short walk to the restaurants. Perfect for R&R.

Top Guest favourite
The exterior of Studio455 is depicted, showcasing a charming white cottage with a shingle facade. Large black-framed doors open onto a small stoop, while soft landscaping features low bushes and greenery. Warm lights line the eaves, providing a welcoming touch.
Guesthouse in Sonoma
4.97 out of 5 average rating, 696 reviews

Modern and Luxe: Studio455 (+bikes)

Centrally located and close to everything in the Sonoma Valley, Studio455 provides guests with a roomy sectional sofa, a king-sized Tempur-pedic bed dressed in dreamy, high-quality linens, and a stylish, modern bathroom. The aesthetic is clean-lined but the furnishings are soft and comfortable. Kick back in front of the huge television after a day of sightseeing, or get comfy on the small private patio with coffee or cocktails in a location just minutes from Sonoma's famous downtown square.

Top Guest favourite
The exterior of The Barn is showcased with rustic wooden siding and a metal roof. A prominent 'Sonoma' sign made of rust-colored metal is positioned in front, surrounded by natural landscaping that includes shrubs and decorative plants.
Guesthouse in Sonoma
4.99 out of 5 average rating, 296 reviews

The Barn (with Electric car charging station)

On the outside, it looks like a barn. However, on the inside it’s like a modern hotel suite. On a country lane just outside the town limits, The Barn is the perfect spot for a getaway. When it’s time to relax, you can lounge in the living room with the big screen, cozy up to a good book, or relax on the porch. When it’s time to explore, we are a few minutes away from the Plaza, 400+ wineries and wonderful food options. TOT Certificate 3235N. Check us out on Insta: the_barn_sonoma

Top Guest favourite
Guesthouse in Sonoma
4.99 out of 5 average rating, 246 reviews

707 BARREL LOUNGE Cottage

LIVE ALOHA IN SONOMA! Enjoy this tropical Hawaiian Getaway in the Heart of Sonoma Wine Country. Sonoma is a great little town to eat, drink, shop, hike, bike, walk, swim, and relax. There is so much to do here! This cottage will put you in a vacation state of mind as soon as you arrive. Relax around the pool, enjoy a good book, walk into town or hire a car service and visit some of the many amazing wineries in the Sonoma-Napa-Alexander Valleys. COME ENJOY ALOHA IN SONOMA!

Top Guest favourite
Guesthouse in Little River
4.94 out of 5 average rating, 234 reviews

Mendocino Coast Townhouse - OCEAN VIEWS

Unwind in a modern bohemian retreat on the breathtaking Mendocino Coast. This spacious townhouse with 1 bedroom and 1.5 bathrooms features a plush king-size memory foam bed, natural decor elements, and inviting furnishings. A fully equipped kitchen with stainless steel appliances and butcher block countertops is perfect for cooking delicious meals. Enjoy stunning ocean views from the cozy bedroom balcony. The en-suite bathroom features a convenient double vanity.

Guest favourite
A tranquil pool reflects the vibrant hues of a sunset, bordered by lush greenery and palm trees. Comfortable seating areas are visible under shaded structures, enhancing an inviting outdoor space surrounded by colorful landscaping.
Guesthouse in Sonoma
4.91 out of 5 average rating, 322 reviews

Romantic Tropical Garden Casita

As you step through the entrance and under the arch, you are transformed into another time and place. We have been told by guests they feel it reminds them of Italy, France, and Spain. The Hacienda is very private, behind the walls of the early California style home. The gardens are lush and filled with birds of all kinds. There are several vignettes to relax and watch nature. Nights are cool so there is no need for A/C if you leave window open at night.

Top Guest favourite
A bright and airy living space includes a comfortable seating area featuring a cozy sofa and an accent chair. A modern dining table with two chairs is positioned next to a wall-mounted television. Light streams in through large windows, illuminating the space with a serene ambiance.
Guesthouse in Sonoma
4.98 out of 5 average rating, 161 reviews

Sonoma Wine Country Haven

ADORABLE WINE COUNTRY HAVEN In the heart of Sonoma, Boyes Hot Springs, walking distance to El Molino, Taqueria La Hacienda, Sonoma Eats (coffee and pastries too) 10 mins. drive to Sonoma Square. Perfect getaway for wine tasting & sightseeing. Join your events & wedding party. Enjoy this tranquil & private haven. Great care has been given to design with modern & cosy comforts. Open the french doors and sit on your private deck. Relax & enjoy.

Top Guest favourite
The modern container home is surrounded by lush greenery and grapevines. Floor-to-ceiling windows reflect the natural light, offering unobstructed views of the landscape. The structure is elevated, enhancing the connection to the surrounding redwoods and vineyards.
Guesthouse in Sebastopol
5 out of 5 average rating, 187 reviews

Modern Container Home with Vineyard Views [NEW]

Welcome to Luna Luna House! - A modern container home, turned one-of-a-kind vacation retreat. Where the redwoods meet the vineyards, a serene sanctuary has been thoughtfully crafted where you can unwind and recharge. Luna Luna House is truly a place to commune with nature, enjoy modern conveniences, and indulge in an unforgettable travel experience! - * Designed by Owners + Honomobo Canada * Former location of The Rising Moon Yurt -

Top Guest favourite
A cozy sitting area features a blue sofa adorned with colorful throw pillows and a red accent pillow. A wooden coffee table rests on a soft area rug, while a small desk and chair provide a workspace. Decorative elements include plants and artwork on the wall.
Guesthouse in Santa Rosa
4.96 out of 5 average rating, 289 reviews

Wine Country Retreat - Chic Sonoma County Getaway

Our retreat is located in the heart of Sonoma's wine country - close to wineries, breweries, restaurants and several state parks all less than 20 min away: Annadel State Park (4 mi) Spring Lake (3 mi), Sugarloaf Ridge State Park (10 mi). It's stylishly decorated, clean, modern and quiet. We offer a new King bed, private entrance, attached bathroom, off-street parking, and kitchenette. The space is newly built and ready for you to enjoy.

Top Guest favourite
A modern cottage is set against a backdrop of vibrant landscaping, showcasing a large, clear salt-water pool. Various outdoor seating areas are visible, complemented by lush trees and greenery that enhance the serene environment.
Guesthouse in Sonoma
4.95 out of 5 average rating, 269 reviews

Wine Country Gem - Sonoma Cottage with Pool Oasis

Charming Sonoma cottage perfect for a romantic getaway, girls’ trip, or family stay. Explore Sonoma, Glen Ellen & Napa with ease. The private unit has gourmet appliances, a minimalist-country style, and its own deck with dining + lounge seating. The peaceful 1-acre property features vineyards, a large saltwater pool, a veggie + herb garden, and fruit trees. Relax, recharge, and enjoy the best of wine country living. TOT #3140N

Top Guest favourite
A bright living area features a spacious white sectional couch and a wooden coffee table. An expansive bookshelf holds various items, with a television and fireplace being focal points. Large glass doors open to a garden, bringing in natural light and outdoor views.
Guesthouse in Healdsburg
4.97 out of 5 average rating, 219 reviews

Healdsburg Contemporary Cottage With Lush Backyard Patio

Your private Healdsburg retreat—just a 4-minute walk to downtown wine tasting rooms, restaurants, shops, and the Farmers Market. This stylish guest cottage offers parking in front of a private entry, garden with al fresco dining, BBQ, lounge area, and a fully equipped Pilates studio. Designed with international contemporary art and thoughtful touches, it’s perfect for a weekend escape or a longer stay while house hunting.

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