Guesthouse vacation rentals in Woodside

This beautiful Oakland Oasis was better than I imagined it would be! This place exceeded my expectations! Coming through the gate the first night, to a path of twinkling lights leading us to our adorable cabin took my breath away! It was the perfect location for peace and quiet right in the middle of Oakland. My only regret is that I didn’t spend more time on the property. We flew in from out of state to visit friends and spent a lot of time out and about. I definitely want to come back to spend more time hanging out in the backyard with the goats and chickens. My 13-year-old loved the backyard, the trampoline and the animals. The location was very walkable and within several blocks of many restaurants and shops. We rented a car and street parking was easily accessible. Reinhardt Redwood Regional Park was only an 8 minute drive away and we spent most mornings walking through the mountains enjoying the beautiful trees and views of San Francisco. Highly recommend this listing!

Very friendly and proactive host. Praceful and quiet location. Several pieces of lovely fruit were provided, as well as flavored sparkling water, milk, and granola/muesli, which was really convenient. Showerhead can be adjusted for angle and whether you want a straighter stream straight down, or a wider spray. I appreciated that there was a screen on the window so it was easy to get fresh air when I wanted while keeping bugs out. I suggest trying to time your arrival the first day during daylight hours, as that will make it easier to see the signs, especially when Google Maps is off by a few yards in terms of where it tells you to turn.

Amy's place was wonderful - one of the few places we've ever stayed that was even better in person than in pictures. It was clean, spacious, and very comfortable for the 2 of us. The outdoor space was amazing, plenty of quiet spaces to lounge in the sun and walk around. The area was great as well, quiet but close to downtown, and Amy was a thoughtful and responsive host, we really appreciated her thoughtfulness. The one thing to note is that the Wi-fi could be unreliable - we both worked from the Airbnb, and made it work for the week, but something to note for future visitors. We'd definitely recommend this place and plan to come back next time we visit. Thank you Amy!

This was an EXCELLENT Airbnb. Great value, beautiful property, plenty of privacy, exceptionally good instructions form the hosts. I can not recommend highly enough. Great place to recharge.

This was a perfect place to decompress during a busy work trip. The space is beautiful, and the attached gym is such a nice treat! Everything was exactly as described, clean and lovely. I would definitely stay again!

Had an absolutely lovely stay at Rezan’s place. She was the utmost in hospitableness and thoughtfulness The property is absolutely gorgeous, filled with birds and trees and flowers and the sound of frogs, statuary, walking paths, places to sit and enjoy the environment, a little pond with fountain, and just minutes to downtown Los Gatos. I had the best stay.

Ray’s place is like a home away from home tor us and we appreciate especially his accommodating change that arose this trip - quiet house, convenient location, and everything we needed.

Kate’s place was great for our family of four while we visited San Francisco. The immediate area was clean and felt safe, and a variety of food and shops were within walkable distances. Access to the Caltrain was also close by. As for the house, it had everything our family needed but may be a bit tight for groups larger than 4, especially if they are all adults. Amenities were as listed and made the stay comfortable. Kate and Toni were responsive very quickly and helped us with everything we needed. Highly recommend!

Super cute place! Our kids loved the ducks and horses across the street. They couldn’t wait to explore! The house is very well stocked- games, kids toys, cookware, laundry soap… everything you can think of! We had a really great time, and it’s such a unique place to get to stay!

The host had a beautiful place and was quick to answer any questions we had. Would recommend to anyone staying in the San Jose area.

Marilynn has been great and very responsive when we have stayed there. The place is well-stocked and maintained, and San Carlos is a friendly town with good restaurants and boutique shopping.

I stay here whenever I'm in town absolutely my fav. Host is amazing and love her house! Thanks, Taylor!!

This place was so beautiful, the pictures didn’t do it justice. Perfect location close enough to restaurants, and lil shops!! Just away enough out of the city, but not to far out. Would definitely recommend to anyone wanting a nice cozy easy place to get to. Also my wife’s 50th birthday and I asked him to do something special for her birthday and he put out a birthday banner and a bottle of champagne!!

This is an absolute hidden gem. It quickly became apparent why Carolyn is a super host. Not only is the property absolute perfection but Carolyn made it a point to go out of her way to welcome us, accommodate us, and go above and beyond customer service wise. This property radiates harmonious zen like energy from the community library, to its amenities and all its extra additives, to the garden. It’s graced with every bit of detail for guests to enjoy. I’ve loved traveling and have mostly been a hotel snob, until now. In short, Carolyn has carefully crafted a beautiful get away and decided to share it with the world. We will certainly be back when in town.

The attention to detail was excellent. The landscaping and the interior was very serene. And immaculately kept.

Fabulous! Darling little studio ADU. Sparking clean and beautifully appointed. Loved staying here and will again.

We thoroughly enjoyed our stay! The space was clean, comfortable, and exactly as described. It had everything we needed for a relaxing and enjoyable visit. Christina and her family were extremely kind and helpful, check-in was seamless and communication was easy. We’d happily stay here again and would definitely recommend it to others! Thank you for having us!

Our stay at Kyle’s was lovely and easy! It was a perfect home base for our adventures in the nearby state parks. The chickens are very cute, but if you’re a light sleeper looking for quiet, you may hear them in the morning. The eggs are amazing and such a wonderful addition to a comfortable stay. We had everything we needed and then some! Would definitely stay again during a trip to the Santa Cruz area.

My grandpa and grandma stayed here and they said this was the best bead and breakfast they have experienced in their life. huge thanks to Silvia for being responsive and making my grandparents feel at home!

Highly recommend. Central to the Bay Area and major freeways. Clean and quiet. Easy access and private parking. Everything was perfect. This is my second time staying and will be staying again! Thank you!!

Amazing stay at this cozy cabin by the sea. We enjoyed sitting on the balcony and listening to the sound of waves. The place is incredibly well-stocked with everything we needed — from kitchen supplies to dog blankets and groceries. Thank you!

Our stay was excellent. The place was very clean and well-maintained. Communication with the host was quick, and they were always available for any questions or recommendations. I would definitely recommend this place to other travelers and would stay here again in the future.

David and Margaret were wonderful people! They stayed on top of communication and they were very kind. We only stayed for a night but their backyard is beautiful, the room and interior had everything you needed and it was private. For the area, the room, and the scenery- definitely a great place to stay. They also had a nice fan and wall AC which was so nice with the warmer weather kicking in during the day.

We chose this stay to host guests over the holidays and it had everything we could’ve needed. The kitchen was functional for cooking breakfast and the rooms were very private and had their own bathrooms. Xing Tian was very helpful when we needed an extra gate key, and when we had any questions. We’ll definitely be coming back!