Guesthouse vacation rentals in Woodside

Guesthouse in Professorville

A bright and airy room is fitted with a spacious bed, complemented by a large window and a skylight overhead. A wooden desk and ergonomic chair are positioned for work, while a simple decorative piece adorns the wall. The room offers a private entrance.

4.93 out of 5 average rating, 228 reviews

Downtown Palo Alto Gem! Cute, Spotless Guest House

We invite you to stay in our private, remodeled guest house. It's an easy walk to the restaurants and shops on University Avenue, in a safe and sought-after neighborhood in Downtown Palo Alto. The guest house was recently renovated and has a gorgeous bay window, air conditioning, two skylights, and a spa-like bathroom. We pride ourselves in keeping it absolutely spotless. The studio cottage is 200 square feet. It’s perfect for a single person but has a queen bed, so can accommodate a couple

A rustic cabin is situated among tall redwood trees. A wooden deck extends towards a tranquil pool, which is surrounded by greenery and flower beds. The warm tones of the cabin's exterior complement the natural surroundings, enhancing the serene atmosphere.

4.99 out of 5 average rating, 353 reviews

Rustic Cabin in the Redwoods

Tucked among the redwood trees on top of King's Mountain, this 1 bedroom cabin offers both rustic charm and modern luxury. Property owners live onsite in the main house about 30 feet away from the cabin. Located just 20 minutes off HWY 280, this cabin is the perfect weekend retreat for those looking to get away from the bay area without actually leaving. Spend time relaxing in the pool, hiking or biking one of the nearby trails, or just reading a book while sitting among the redwood trees.

Superhost

The living area features a blue velvet sofa and a white upholstered couch, positioned around a wooden coffee table. Two framed photographs adorn the green walls, with light filtering through nearby windows. A decorative plant hangs in one corner, adding a touch of greenery.

Guesthouse in Half Moon Bay

4.88 out of 5 average rating, 339 reviews

Stylish Spacious Seaside Retreat, Walking to Beach

A perfect getaway on the coast with fresh air, sandy beaches, biking/hiking trails, and quaint restaurants, our place is 10minutes walk to the famous Maverick Beach, Sam Chowder House, and the Harbor. This stylish guest house is the 1st floor of our seldom used beach house in El Granada, 4 miles north of Half Moon Bay. It has a private entry, a fully equipped kitchen, w/ a laundry/mud room & on-site parking. Large decks have splendid ocean view! Come and enjoy this quiet and comfortable home.

Guesthouse in Edgewood Park

A modern kitchen is highlighted by a spacious granite countertop island with four wooden stools. Natural light pours in through a large window overlooking the garden, illuminating stainless steel appliances and cabinetry. Plants add a touch of greenery to the inviting space.

4.99 out of 5 average rating, 117 reviews

Private Cottage near Redwood City and San Carlos Downtowns

Quiet, private two-level garden cottage ideal for business travelers and visiting family. Gig+ high-speed Wi-Fi, workspace, central AC & heat, king-size bed, private entry (24/7), 50” 4K TV, fully equipped kitchen with granite countertops, and guest-exclusive washer and dryer. Bedroom, living area, kitchen, bathroom, and dining / work space. Shared garden with BBQ, teak table and hot tub. Walkable to transit, downtown areas, and a popular breakfast café. Some train and light traffic noise.

A cozy living area features a gas fireplace, providing warmth. A television is mounted above, and natural light enters through two windows. A round red rug is positioned on the hardwood floor, with a light-colored sofa and a dark chair visible, creating an inviting space.

4.98 out of 5 average rating, 453 reviews

Kings Mountain Studio Cabin

Enjoy a cozy STUDIO Cabin nestled in the Redwoods up on Kings Mountain. For those who are inclined to have an active lifestyle, We are close to Purisima Creek, Huddart Park, and El Corte De Madera Hiking and Biking Trails. This space is perfect for two! (read more about the space) 20 minutes away from Half Moon Bay with beautiful beaches and 30 min. from Stanford, Palo Alto. We are adjacent to The Mountain House Restaurant. Res recommended. Short drive to local breakfast place. NO PETS!

Tall redwood trees rise from the forest floor, creating a serene canopy. A distant view of the bay is visible through the trees, with a blanket of clouds resting over the landscape. The sky is clear, contrasting with the lush greenery of the forest.

4.97 out of 5 average rating, 336 reviews

SkyHigh Redwoods Retreat with Bay Views

Inhale. Exhale. Relax in this cozy, romantic guesthouse retreat nestled in the redwoods of the Santa Cruz Mountains, overlooking the bay and conveniently located near the famous Alice’s Restaurant on Skyline Blvd in Woodside. The 1 acre gated property has ample parking and privacy. Snuggle in with the wood burning fireplace, prepare meals in the full size kitchen and take in the views of the majestic redwoods right outside the windows with bay views peeking through the trees.

4.99 out of 5 average rating, 131 reviews

A spacious deck features two wooden directors' chairs positioned around a small circular table. Lush greenery lines the perimeter, creating a natural backdrop. A sunshade is partially visible, offering protection from the sunlight.

Guesthouse in San Carlos

Delightful Hideaway in San Carlos

Fully equipped executive studio in the heart of Silicon Valley. This studio is ideal for accommodating executives, visiting doctors and nurses and other professions that might require long term stays. Visitors will enjoy the warm family-friendly environment and delightful garden setting. It is also well-suited for those on vacation who delight in visiting the nearby cities, as well as those who have families close by and want to have their own private spot.

4.96 out of 5 average rating, 114 reviews

A serene beach scene at sunset is captured, featuring gentle waves reflecting the hues of orange and blue in the sky. Silhouettes of people can be seen walking along the shoreline, while lights from the distant marina twinkle against the darkening landscape.

Guesthouse in El Granada

Coastal Cottage Guest House

Guest house is attached to our primary residence but has a separate exterior entrance. The interior is separated by double doors that lock from both sides, similar to adjoining hotel rooms. The backyard is shared by us, the owners. There’s a very real chance you’ll be greeted by our friendly Australian Shepherd, Gracie, during your stay! You may see us in the yard during your stay. Feel free to say hi! Otherwise, we like to give our guests privacy.

Guesthouse in Portola Valley

An outdoor deck features two green cushioned chairs and a wooden table at its center. A potted plant is placed on the table, complementing the natural setting. The entrance door, framed in black, leads into the guesthouse, surrounded by tall trees.

4.94 out of 5 average rating, 216 reviews

Woodsy Silicon Valley Cottage

Discover a laid-back side of Silicon Valley in a cozy, cedar-shake guesthouse surrounded by mature trees. Walking distance from a great network of destination hiking and biking trails. 15-30 minutes from Stanford, Sand Hill Road, and major tech companies. This 400 square foot space is on top of our garage and next to our home. There is no public transportation nearby and ride share services are available but not always reliable so you'll need a car.

A spacious bedroom features vaulted wooden ceilings and large glass sliding doors leading to an outdoor deck. A comfortable bed is flanked by two bedside tables with lamps. A decorative painting hangs above the bed, and a wooden dresser adds functional storage.

4.99 out of 5 average rating, 573 reviews

Guest House in the Woods

Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.

Guesthouse in Hillsborough

A spacious room features vaulted ceilings with wooden beams. A queen-sized bed, draped in a geometric patterned blanket, sits next to a sleek fireplace. A dining table and chairs are visible, along with a large TV and two closets that provide storage options.

4.95 out of 5 average rating, 996 reviews

Little Cottage on the Hill

Enjoy a peaceful stay at this charming, secluded detached garden cottage great for a stay-cation or as a work-from-home alternative. Since the coronavirus pandemic, we have been taking extra care to disinfect frequently touched surfaces between reservations. The cottage features a queen-sized bed, a fireplace, private bathroom and kitchenette. Perfect for both leisure and Business travelers.

4.99 out of 5 average rating, 245 reviews

A dining area features a round table surrounded by four white chairs, illuminated by a decorative chandelier. Natural light enters through large windows adorned with sheer curtains, complementing the light green walls and adding a bright, open feel to the space.

Guesthouse in Sunnyvale

Lush Lux Villa • Sunny Deck & Private Escape

Romantic private retreat with sunny deck & lush greenery Indoor/outdoor living, vaulted ceilings, garden views Gourmet kitchen, gas fireplace, walk-in shower Heated towel rack, aroma & sound therapy Nest-controlled A/C & heat (no shared ducts) Air filtration + eco-friendly cleaning Self check-in/out, fast WiFi Ideal for couples, solo travelers & business trips

Popular amenities for Woodside guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

4.96 out of 5 average rating, 112 reviews

A light blue cottage is set amidst lush greenery and towering trees. The exterior features multiple windows, offering views of the surrounding landscape. A narrow pathway leads to the inviting front door, framed by flowering plants, enhancing the tranquil setting.

Guesthouse in Los Gatos

Mountain Retreat

4.94 out of 5 average rating, 570 reviews

Guesthouse in Mt. Carmel

Sunny Redwood City Studio Private Entry

4.87 out of 5 average rating, 301 reviews

A quaint cottage entrance is featured, framed by well-maintained greenery and colorful potted flowers. A striped umbrella provides shade over a small seating area with two chairs and a round table. The door is adorned with a seasonal wreath, enhancing the welcoming atmosphere.

Guesthouse in Stanford

Palo Alto Cottage

Superhost

A serene beach scene captures the golden sun setting over the calm ocean waters. Silhouettes of distant hills align with the horizon, while the sandy shoreline, marked by gentle waves, is framed by lush greenery in the foreground.

Guesthouse in Half Moon Bay

4.82 out of 5 average rating, 551 reviews

Cozy Cabin w/Firepit on the Coast-hear Ocean waves

4.94 out of 5 average rating, 104 reviews

The bedroom features a spacious bed with neutral-toned bedding, accompanied by a desk and a comfortable chair. A wall-mounted TV and a standing heater are visible. Natural light is allowed in through the window, dressed with sheer curtains, creating a calm environment.

Guesthouse in Cupertino

Guesthouse with kitchen,bath and laundry

4.98 out of 5 average rating, 448 reviews

The exterior of the cottage features a welcoming entrance with a white door and a light fixture. Potted plants adorn the side, and a stone pathway leads through a landscaped area. The surrounding trees provide dappled sunlight, enhancing the tranquil outdoor setting.

Guesthouse in Mt. Carmel

Quiet , Private Studio / Cottage

4.98 out of 5 average rating, 469 reviews

A spacious bedroom features a comfortable bed with dark gray bedding, flanked by matching bedside tables and lamps. Two large windows allow natural light to fill the room, highlighting the textured wallpaper and organized bookshelf in the corner.

Guesthouse in Hillsdale

A Comfortable, Clean, & Private Guest House

Guesthouse in Upper Rockridge

The exterior of the cottage is shown, framed by a variety of plants and seasonal foliage. A stone pathway leads to the entrance, which features a white door with a welcoming sign. Bright leaves on nearby trees add color to the scene, enhancing the cottage's charm.

4.96 out of 5 average rating, 151 reviews

The Cottage

Guest house rentals with a patio

Guesthouse in West Oakland

A bright living room features large windows allowing natural light, framed with sheer white curtains. The space includes a comfortable white sofa, a round coffee table, and decorative accents like a geometric art piece and sunflowers placed on the table.

4.94 out of 5 average rating, 112 reviews

Charming Victorian Retreat | Minutes to SF

4.92 out of 5 average rating, 184 reviews

A bright living area features a dark leather sofa adorned with decorative pillows, accompanied by a wooden coffee table. A small table with two chairs is positioned beside a large window, allowing natural light to illuminate the space. A floor lamp and decorative plant enhance the room's inviting feel.

Guesthouse in San Jose

Newly built stylish guesthouse

4.92 out of 5 average rating, 382 reviews

The image depicts a serene garden pathway leading to two adjacent cabins, framed by vibrant greenery and flowering plants. A wooden trellis is visible, providing shelter, while soft lighting from the cabins enhances the calm atmosphere. A mixture of stone and mulch surfaces directs attention toward the entrance.

Guesthouse in Oakland

Guesthouse Garden Retreat

4.9 out of 5 average rating, 112 reviews

A spacious studio is showcased with a large bed and a serene wall mural of trees. Natural light fills the room through sliding glass doors, which lead to the outside garden. A comfortable chair and side table create a cozy seating area.

Guesthouse in Alameda

Detached Cozy Studio w/ private patio garden & BBQ

Guesthouse in Downtown San Jose

An outdoor patio area is shown beneath a wooden pergola adorned with warm string lights, creating a cozy ambiance at night. A large 65-inch TV is mounted on the wall, while comfortable dining and lounging furniture is arranged for relaxation and socializing.

5 out of 5 average rating, 123 reviews

Near Japantown & SJC ARPT, King Bed, Fast Internet

Guesthouse in Midtown Palo Alto

A spacious studio is displayed, featuring a light-filled sleeping area with a cozy bed, adorned with crisp white linens and decorative pillows. A small dining table with two chairs is positioned nearby, along with a stylish desk and chair. Soft lighting enhances the overall warmth of the space.

4.9 out of 5 average rating, 153 reviews

Palo Alto Cottage: Privacy, Comfort & Convenience

Guesthouse in Willow Glen

A bright living area features a light grey sofa with decorative pillows, paired with a round black coffee table. A teal armchair is positioned nearby. Large windows with striped shades allow natural light to fill the space, complemented by a tall indoor plant.

4.94 out of 5 average rating, 105 reviews

Adorable 2 bed guesthouse walk to Willow Glen DWTN

Guesthouse in Santa Clara

A spacious living area is highlighted by a comfortable sofa adorned with decorative pillows. The open kitchen is visible, featuring modern appliances and a dining table. Large windows allow natural light to fill the room, enhancing the airy atmosphere.

4.95 out of 5 average rating, 116 reviews

Santa Clara Guest House w/King Bed and Parking

Guest house rentals with a washer and dryer

Guesthouse in The Willows

A private patio area is featured, furnished with two seating areas and a central table. An umbrella provides shade, while potted plants add greenery to the space. The wooden fence offers privacy, and the stone floor is complemented by a textured outdoor rug.

4.99 out of 5 average rating, 160 reviews

Quaint Cottage Near Downtown Palo Alto

Superhost

The open living area features a comfortable sofa and a dining table with two chairs. A well-equipped kitchenette is visible, along with a large TV set against the wall. Natural light brightens the space through a window, enhancing the welcoming environment.

Guesthouse in Lakeside

4.87 out of 5 average rating, 130 reviews

Newly Remodel Guest Suite-Separate Entrance

Guesthouse in Downtown San Jose

A cozy living area features a stylish brown leather sofa and a round dining table accompanied by black chairs. Large glass doors invite natural light and provide views of the shared backyard. A modern kitchen is situated in the background, enhancing the open layout.

4.98 out of 5 average rating, 239 reviews

Private Abodu Guesthouse in Downtown San Jose

4.92 out of 5 average rating, 169 reviews

A modern dining area features a long white table set with turquoise plates, surrounded by brown chairs. In the background, a well-equipped kitchen showcases dark wood cabinets and stainless steel appliances. A spacious living area is visible, brightened by natural light from large windows.

Guesthouse in Lakewood

Spacious 4B2B Levis/GreatAmerica/ConventionCtr

4.97 out of 5 average rating, 394 reviews

The entrance of the cottage features a welcoming white door with a clear window, flanked by decorative plants in a variety of pots. A wooden bench sits beneath the windows, adding a functional touch to the inviting exterior.

Guesthouse in San Jose

Private unit close to Santa Clara University

Guesthouse in Allied Arts

A combined living and kitchen area is shown, featuring a brown leather sofa and a wooden coffee table. A plaid patterned chair adds a pop of color. A flat-screen TV is mounted on the wall, and natural light fills the space through doorways leading outside.

4.91 out of 5 average rating, 140 reviews

Menlo Park 2 Bedr Cottage

4.96 out of 5 average rating, 302 reviews

The exterior of the recently renovated garden unit displays a soft green facade with a welcoming white entrance door. Decorative windows are positioned above the door, enhancing natural light. A wooden deck leads to the entrance, framed by lush vegetation and a bicycle is parked nearby.

Guesthouse in Broadmoor

Garden getaway near SF