Guesthouse vacation rentals in Woodside

Modern Stanford/Palo Alto Guest House

Forty-One Oaks guest house is in a beautiful, serene, treed setting just minutes from I-280 and access to Palo Alto, Stanford, Silicon Valley, San Francisco, and the rest of the Bay Area. The award-winning three-acre property is called 'Forty-One Oaks' because of the glorious woodland setting, with 41 significant oak trees. See families of deer, turkey, hawks, owls, and other wildlife right out your window. Catch a look of the famous Stanford 'dish' radio-telescope from your living room window.

Mt Carmel Cottage Charmer-Bright, Stylish & Clean

Beautifully well-appointed cottage with a private entrance, designed for comfort, style, and privacy—ideal for couples, solo travelers, and business stays. The space is meticulously maintained to provide a clean, relaxing, and comfortable experience. Located within walking distance to Caltrain (0.9 miles) and downtown Redwood City (0.6 miles), offering access to boutiques, cafes, restaurants, parks, and a movie theater. Seamless access to Palo Alto, San Francisco and the greater Silicon Valley.

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.

Fabulous Guesthouse next to Stanford w/ Kitchen

Our Menlo Park home is walking/biking distance from Stanford and offers tons of privacy, tranquility and comfort for business professionals or anyone coming to visit Stanford! The main sleeping area is downstairs with all new linens plus an upstairs loft area with two twin beds. Families or co-workers can comfortably stay here! We are SuperHosts and have taken a lot of care to set this space up with all of the amenities you might need, including a desk, kitchen area and beautiful outdoor area!

Stylish Seaside Cottage - Walking to Beach

A perfect place for romantic getaways! newly built on top of our detached garage, 10mins walk to beach! private entrance, smart lock, modern skylights, quality linens, trendy decor, private deck with splendid ocean view, on-site parking! At the sunny beautiful El Granada, 4miles north of Half Moon Bay, a lot of fun activities: spending your days on the beach, exploring the hiking trails, trying out many local restaurants, or road trip along Highway 1, 30 mins to SF or 60 mins to Santa Cruz.

Kings Mountain Studio Cabin

Enjoy a cozy STUDIO Cabin nestled in the Redwoods up on Kings Mountain. For those inclined toward an active lifestyle, we are close to Purisima Creek, Huddart Park, and the El Corte de Madera Hiking and Biking Trails. This space is perfect for two! (read more about the space)Note 20 minutes from Half Moon Bay with beautiful beaches and 30 min from Stanford in Palo Alto. We are adjacent to The Mountain House Restaurant. (note) The bed is a Murphy bed in the living area. NO PETS!

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.

Sunny Cottage in Redwood City

This charming petite maison will have you at bonjour! Surrounded by greenery and flooded with natural light, this spacious cottage has everything you need for a work stay or vacation getaway. Private entrance and patio, outdoor seating, spacious indoors with a modest living room, kitchen, bathroom, and bedroom with workspace. Ample street parking just a few steps from entrance. Located close to downtown Redwood City and easy access to both the 280 and 101 freeways.

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.

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.

Charming Studio Garden Cottage near Stanford

Come and relax in our light and airy studio cottage situated in a beautiful garden setting, the perfect get-away after a day of business meetings or visiting with family. We are close to major Silicon Valley destinations as well as Stanford Hospital, 45 minutes' drive from San Francisco, San Jose and the beach in Half Moon Bay — easy access to Highways 101 and 280. Our quiet neighborhood full of mature oak trees beckons you to take a walk.

Bicycle Shack @ La Honda Pottery

My place is close to miles of hiking and biking trails in county parks and openspace, great views, the beach and not far from the Peninsula, S.F. and Santa Cruz. You’ll love my place because of the location, the people, the ambiance, the outdoors space and that it is a self contained small cabin with a tiny deck.. My place is good for couples, solo adventurers, and furry friends (pets). Perfect for hikers and bikers.