Holiday houses in Woodside

4.96 out of 5 average rating, 122 reviews

Home in San Carlos

Serene Oasis in the Midst of Silicon Valley

Gaze out at the beautiful green canyon while having a morning coffee in bed. Head to the fully equipped kitchen to prepare breakfast and enjoy it outside on the balcony, surrounded by the sights and sounds of this stunning hilltop location. Close to 280. Centrally located in Silicon Valley for easy access to both San Jose and San Francisco. Deck/BBQ Lounge Area. Minimal. Enjoy life in the San Carlos hills. Drive about 5 minutes to lively San Carlos downtown for several restaurants and bars. Go hiking in Edgewood, Crestview, or Big Canyon. For a taste of big city life, adventure a bit further to San Francisco. Driving is the best option, I280 and 101 are easily accessible. Cal Train station down the hill - connects all the way from San Francisco to San Jose. Very spacious unit ( approximately 1200 sq.ft )

4.81 out of 5 average rating, 223 reviews

Guest suite in Woodside

Central Woodside suite near restaurants with view

Spacious & peaceful one bedroom suite in central woodside. A nice walk or quick drive to Roberts Market and famous restaurants -Bucks, Village Bakery, Village Pub. Unit has spacious living space w pano view of valley & hills. Steps away from hiking & horse riding trails. 20 mins to SFO 35 mins to San Francisco. Quick 10 min drive to Menlo Park/Palo Alto/Stanford. 15-30 mins to Mountain View, Cupertino, San Jose, etc. This unit is on an entire first floor of a two-story home w own entrance.

4.99 out of 5 average rating, 330 reviews

Guesthouse in Woodside

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.

4.99 out of 5 average rating, 724 reviews

Guesthouse in San Carlos

Private Garden Cottage

Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.

4.98 out of 5 average rating, 404 reviews

Cottage in Woodside

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!

4.88 out of 5 average rating, 385 reviews

Guest suite in Woodside

Stay Nestled in Ancient Redwoods in Silicon Valley

Welcome to our 6-acre home, High Ground, & have our kid and pet friendly carriage house to yourself! The large studio apt with separate entrance has stunning views of ancient redwood trees + the Bay/Mount Diablo. Immediate hiking trails, wildlife, minutes to: Alice's restaurant (5), Michelin-rated Village Pub (15) highway 280 (15) Palo Alto/Menlo Park/Half Moon Bay/Ocean (30), SFO (35) San Francisco (45). Perfect for a northern CA retreat, business in the Valley or sight-seeing in San Fran.

Place to stay in Portola Valley

4.86 out of 5 average rating, 148 reviews

Magical 2br/2ba cabins nestled in the redwoods

Nestled into the redwoods of Portola Valley but only 15 minutes from Palo Alto and 25 minutes from SFO, this is a dreamy rustic cabin retreat. We're honored to share it with you. The residence consists of 3 separate cabins built by Yurt People/California Yurts. The cabins are connected by a large deck overlooking a forest creek and enveloped in redwood, oak, and bay trees. You are surrounded by nature and can walk to a large network of public trails. It's a beautiful and magical place.

4.89 out of 5 average rating, 451 reviews

Guest suite in Woodside

Separate entry room near Stanford

This separate entry room opens to a beautiful one-acre garden with a pool, jacuzzi, cable TV/wireless, and parking. We are just off 280 and Woodside Rd., 4 miles from Stanford. It is peaceful and quiet and we are hands-off hosts. There is no access to the house and the room does not have a frig, microwave or dishes. We are set up for independent guests who want to come and go on their own and enjoy local restaurants in Woodside, Palo Alto or RWC. Please note the very short entry door.

4.97 out of 5 average rating, 273 reviews

Guesthouse in Woodside

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.

Guest suite in Emerald Hills

4.92 out of 5 average rating, 182 reviews

Elegant retreat in Redwood City

NOW with new AC & Heating! Gorgeous one bedroom apartment with en-suite bathroom, a spacious walk-in closet, ample light, and stunning views. Private fully equipped kitchen and sitting area allow for very comfortable living. Bedroom and sitting area/kitchen are separated by a door to allow for 2 separate work spaces. Washer/dryer and many other amenities available. This is part of a ~4000 sq ft luxury single family home with a completely separate and private entrance.

Guesthouse in Portola Valley

4.94 out of 5 average rating, 202 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.

4.93 out of 5 average rating, 150 reviews

Guesthouse in Woodside

A beautiful Tree house -your own retreat

This charming 2 bedrooms is nestled among the trees in beautiful Woodside, California. This town is 30 minutes from San Francisco and right behind Stanford University. Our tree house is a private, peaceful, modern and very comfortable detached guest house. The house has a fully equip kitchen, BBQ and very peaceful settings where you can enjoy nature hikes and be surrounded by peaceful trees and yet just minutes away from town.

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Popular amenities for Woodside holiday rentals

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Other great holiday rentals in Woodside

4.97 out of 5 average rating, 33 reviews

Home in Loma Mar

Redwood Treehouse Retreat

MelissaRating, 5 stars2 weeks ago

We loved our stay! The location was ideal for us, just a few minutes from a beautiful redwoods park and a short drive to the coast. This part of California is tucked away from the busy crowds of the Bay Area and feels remote. The Loma Mar outpost offers basic provisions and a restaurant a few minutes from the house, and Pescadero has a strip of shops and restaurants about ten minutes away. The house is lovely and comfortable, very peaceful.

Guesthouse in Emerald Hills

4.79 out of 5 average rating, 38 reviews

A freestanding casita in a delightful grape garden

JasonRating, 5 stars1 month ago

Me and my girlfriend needed a little getaway and this was perfect. There was a small ant problem and Maria had someone there to take care of it within an hour. Would highly recommend.

4.93 out of 5 average rating, 69 reviews

Cabin in Felton

Santa Cruz A-Frame

YangRating, 5 stars2 weeks ago

The Santa Cruz A-frame was such a serene retreat into the mountains for us, and an antidote to our overly digital and urban lives. Things we appreciated: easy parking, both an upstairs and downstairs bathroom, full kitchen supplies, private balcony, gorgeous forest views, creek in the back, and easy access to Loch Lomond (peddle boating on the lake was so peaceful), the redwood state park (hiking in the largely shaded trail was great on an otherwise sunny day), and local groceries and food (enjoyed the cute outdoor patio in the back of The Grove cafe and bakery). We had a wonderful rest!

Guesthouse in Redwood City

4.9 out of 5 average rating, 72 reviews

Sunny Cottage in Redwood City

JoeRating, 5 stars4 weeks ago

Great place, very clean and has everything you need. Also has a very nice, private outdoor seating area. The location is central to the peninsula. Would definitely stay here again!

Guesthouse in Redwood City

4.96 out of 5 average rating, 27 reviews

Cottage. 15 Mins to train/dwntwn

MegRating, 5 stars2 weeks ago

Jo Ann’s place is super cute, clean, and has everything you need. The location was great for me and the selling points for me are the privacy and quietness. Will definitely stay again.

Guesthouse in Redwood City

4.81 out of 5 average rating, 36 reviews

Detached Guesthouse with Stunning Bay Area Views

KacperRating, 5 stars3 weeks ago

This was a perfect getaway from the city. The place was cleaned and looked exactly as in the photos. The neighborhood is quiet and surrounded by beautiful views, perfect for relaxing. I definitely recommend it.

4.89 out of 5 average rating, 19 reviews

Guesthouse in La Honda

Cozy Barn Retreat

ClassyRating, 5 stars1 week ago

loved this little barn. perfect for our stay and had everythingbee needed. I even met Jessica who is a doll and super sweet and had helpful info for us to pick up some produce. This place was very good an quiet. Away from the street noise and close to everything we needed. Would definitely stay here again.