Guesthouse vacation rentals in Woodside

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Top-rated guesthouse rentals in Woodside

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Guest favorite

Guesthouse in Redwood City

4.93 out of 5 average rating, 298 reviews

Soak up the Serenity on the Patio of a Charming Cottage

Light the fire pit and dress for dinner in the vine-covered garden at a peaceful retreat with a soothing waterfall. Zen beachy decor and coastal paintings set the scene indoors, with abundant natural light enhancing easy open-plan living. Pets are welcome with a small cleaning fee of a $50 (one time fee) and additional pets $25 (one time fee). The main room is 12'x17'. Closet is 6 1/2' long. Bathroom 4'x5 1/2' + shower 3'3" x 3'3". kitchen 4 1/2' x 8". Simple breakfast served. Your own private entrance, plenty of parking on the street, nice neighborhood. We are available if you have any questions or need information on the area. 2 night minimum please. The cottage is tucked away off the street in a quiet, safe neighborhood where residents walk their dogs in pleasant weather. Nearby downtown Redwood City is home to shops and groceries and freeways and public transportation are within easy reach. There is a bus that runs at the corner of our block, it would take you to downtown Redwood City or travel down the El Camino Real. There is a train depot downtown as well. Pets - 2 small dogs in the main house, 2 outdoor cats.

Jan 5 – 12

€ 120 per night

Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 275 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.

Oct 9 – 16

€ 323 per night

Guest favorite

Guesthouse in San Carlos

4.99 out of 5 average rating, 594 reviews

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.

Jul 8 – 15

€ 148 per night

Guest favorite

Guesthouse in Menlo Park

4.95 out of 5 average rating, 159 reviews

Charming, modern, restorative, private studio

Quiet, modern, restorative studio with private entrance and private garden. Mature trees and three skylights makes it feel like you're staying in a tree house. Fiber optics and luxe amenities keep it 21st century. Centrally located to all locations, 20 minutes to SF and SJ Airports, only 30 minutes to Oakland. A quick bike ride to FB, Stanford, and all places high tech. Sip coffee as you work from your laptop in your private garden, then walk to some of the best taquerias in the Bay Area.

Sep 6 – 13

€ 125 per night

Guest favorite

Guesthouse in Woodside

4.97 out of 5 average rating, 156 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.

Dec 4 – 11

€ 206 per night

Guest favorite

Guesthouse in Portola Valley

4.94 out of 5 average rating, 170 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.

Aug 26 – Sep 2

€ 162 per night

Guest favorite

Guesthouse in Woodside

4.94 out of 5 average rating, 107 reviews

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.

Nov 21 – 28

€ 449 per night

Guest favorite

Guesthouse in La Honda

4.95 out of 5 average rating, 383 reviews

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.

Mar 28 – Apr 4

€ 113 per night

Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 485 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.

Mar 24 – 31

€ 222 per night

Guest favorite

Guesthouse in Redwood City

4.89 out of 5 average rating, 161 reviews

Modern Studio Cottage with Private Entrance

Beautiful modern 200 sq. ft. studio / cottage behind main house, with kitchenette, appliances, bathroom, and private entrance. Delicious fruit trees surround the property and are free for the picking! 20 miles to San Jose and 30 miles to San Francisco downtown areas. 4 miles from Stanford University. Great for couples, business travelers, and solo adventurers!

Feb 10 – 17

€ 140 per night

Guest favorite

Guesthouse in Redwood City

4.95 out of 5 average rating, 504 reviews

Stylish Separate Loft/Cottage Walk to Redwood City

* Automated, simple, quick self check in! * Located in a quaint and desirable neighborhood in Redwood City * 15 minutes from Stanford * 5 minutes to the 101 and 280 freeways * Easy walking distance to fun and lively downtown Redwood City/Train * No pets, no pets, no pets

Sep 18 – 25

€ 164 per night

Guest favorite

Guesthouse in Sunnyvale

4.96 out of 5 average rating, 387 reviews

Private cottage in a garden

Charming, private backyard studio cottage nestled in a fenced garden in a quiet Sunnyvale neighborhood. Private, clean and cozy, this 240-sq ft space has a kitchenette, bathroom with shower, full-size bed, Wifi, A/C. Short walk to cafes, groceries. Ample parking.

Dec 27 – Jan 3

€ 128 per night