
Guesthouse vacation rentals in Woodside
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Top-rated guesthouse rentals in Woodside
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Popular amenities for Woodside guesthouse rentals
Family-friendly guest house rentals

82 “ Pool, Jacuzzi , HOT SAUNA, VIEWS, Newer ADU!
simply Laura's family are so wonderful hostess, beautiful persons and the house is very nice place, peaceful, beautiful and for my wife and I will be thinking to return again soon.

Coastal Cabin-outdoor Firepit near Trails & Harbor
Really cool and thoughtful garden Joshua and his dad built! We had a chill and relaxed stay. Also appreciated their recommendations for nearby cycling routes!

Quiet , Private Studio / Cottage
We really enjoyed our stay here. It was really clean, comfortable, and best of all very quiet. Also, the neighborhood is great. We would definitely stay here again if we were to visit the area another time.

Greenwood Guest House, a Peaceful Oasis
My stay in Amy's home was relaxing, peaceful and comfortable. I loved the location - nested against the hills and so close to shops/restaurants. I loved walking the hills in the neighborhood and coming back to a quiet and comfortable space. You are in the backyard of the owners but they are friendly and respectful and the setting is idyllic.

Little Cottage on the Hill
Great location and stay. I was traveling with my wife and baby. Radhia was extremely understanding and flexible with check-in. The space itself was a little small for three but we made it work.

Cottage near dwntwn Palo Alto, Stanford, Face-book
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!

Spacious cottage near downtown & Stanford with AC
This is the third time we stay in Tracy's place, and it's always a great pleasure. The location is great, the house is very well equipped, clean and very comfortable. Tracy responds quickly to any messages and really makes us feel at home. Will keep coming back :)

Private cottage in a garden
Was a great option for close proximity to the Google campus which is where we needed to be. Neighborhood seemed to be safe and walkable. It’s evident they are very involved with the beautiful landscaping and gardening on/around the property therefore notable tree pollen/allergens during the spring time. Overall a cute, cozy, and darling stay!
Guest house rentals with a patio

Cozy Private 1B1B Cottage near Japantown
The cottage was absolutely beautiful! Very accommodating and very clean and quiet. Arthur was the perfect host! Our only issue was the parking. We were in San Jose for a church conference that took place off of 1st Street near 237. We wouldn't get back to the cottage until after 10 p.m. so had to park a block or so away both nights. But, it won't stop us from returning. We will be back for next year's conference. Thanks again Arthur!

Orchard Cottage in convenient countryside location
This was one of the most beautiful airbnbs we’ve stayed in! The house is gorgeous and the property is so cool - our kids loved all of the animals. Laurel is so communicative and helpful. We truly had the best time!

Newly built stylish guesthouse
Yao was a perfect host. She was always responsive to my inquires and was very accommodating when I asked for an earlier check in. Yao Airbnb was very clean, in a quite neighborhood and just a short drive to Kaiser Santa Clara where I had an early morning appointment.

Guesthouse Garden Retreat
This was our first time staying in a guesthouse, and sharing a space with the owners, and I was completely blown away, we both felt right at home, so much so we didn’t wanna leave haha. Victor and Michelle gave us our privacy but also complete freedom to play music, relax on the patio, and roam around their absolutely beautiful backyard. We were able to come and go as we please and always know our things would be safe. The kitchen had everything you could need, the bed was extra comfy and the shower was a DREAM, the whole experience was incredibly cozy and peaceful. This was truly the best place we both have ever stayed, 1000% would recommend!!!

Boho beach bungalow- walk to Poplar Beach
Our stay at this Airbnb was fantastic! The space is beautifully decorated, very clean, and thoughtfully equipped. One of the highlights was the bed, it even has a built-in massager, which was such a relaxing treat after a day of exploring. The kitchen is fully equipped with everything you need to cook or just enjoy a cozy night in. If you’re planning a trip to Half Moon Bay, make sure to stop by Sam’s Chowder House, it’s an absolute must. The food there is unbelievable! The only small issue we ran into was with the shower. The water tends to splash out, even reaching into the bedroom area. It wasn’t a deal-breaker for us, but just something to be aware of. Overall, we had a wonderful experience and would definitely come back. Highly recommend this place!

Palo Alto Cottage: Privacy, Comfort & Convenience
Host was super friendly and responsive. Highly recommend!

Charming, modern, restorative, private studio
We loved our stay at Julie’s studio. It was such a beautiful space and perfect for our needs. The outdoor area is beautiful and the inside is cozy and so well put together. We enjoyed walking in the neighborhood to get delicious food. Would definitely stay again!

Entire guesthouse Santa Clara smart lock entrance.
I’m native to Santa Clara and wanted a brief staycation to help get some focus time/R&R. Katie’s place was perfect for this! Great location, easy to check in and out. Katie was very responsive when I had questions during check in. Overall, I enjoyed my time and would definitely come back!
Guest house rentals with a washer and dryer

Redwood Heights Cottage with Stunning Bay Views
Sarah’s place was really cozy and quiet! We spent a lot of time in SF but it was really nice coming back to the cottage and sleep in the comfortable bed! We would definitely stay again. It wasn’t too far from public transportation and the view was amazing! The kitchen had everything we needed and we really enjoyed cooking breakfast and dinner with the view!

Cottage near downtown Palo Alto
I've stayed in at least a half dozen other airbnb places in the Palo Alto/Menlo Park area over the last years, and this location was by far the nicest. It's very quiet and nicely appointed; easy parking and easy access; close to downtown Palo Alto; and above all, Bob was a wonderful host. Very easy to communicate and responses were almost instantaneous. I hope to have the chance to stay again the next time I'm in the area. Highly recommended.

Stylish Spacious Seaside Retreat, Walking to Beach
We really enjoyed the space… Peaceful and quiet… Tastefully decorated… Perfect for our family of 3… Close to the beaches and lots of good eats to choose from nearby… We will be back.

Private Abodu Guesthouse in Downtown San Jose
Excellent stay! Flora was very responsive and friendly. I will be looking for Flora’s place next time I’m in San Jose.

Private unit close to Santa Clara University
This is our first Airbnb experience and we were glad we chose this place for our first stay. Rahil was a very-very responsive and kind host. We had a tiny bit of trouble first entering the property due to the locking system. I messaged Rahil and he quickly responded and fixed the lock and we were good to go for the rest of our stay. The place was spotless and very clean when we first entered. It is like having your own mini house with all the amenities you need even for a long stay. Everything was professional, instructions were clear, bed and sofa bed were comfortable. The area is super nice and private. It is like a 5 minute drive to Santana Row, Valley Fair Mall, and multiple restaurants. I had no problem keeping my car parked in front of the property and never felt like it was going to be a problem. Overall I would definitely recommend staying at this Airbnb and you are in good hands with Rahil.

Menlo Park 2 Bedr Cottage
Perfect little spot! The cottage was clean, well-maintained, peaceful, and had everything I needed to be very comfortable during my 3-night stay. The neighborhood is gorgeous -- I enjoyed getting outside for exercise every morning. Plus there are plenty of shops and restaurants close by. I would absolutely recommend this place and wish all Airbnbs were so good!!

Tranquil and Charming 1-Bedroom Guest house w/bath
This place was a very cute and peaceful retreat from the daily grind. I only stayed one night but it was everything I needed and expected. Clean and with all the amenities, great stay and I’d stay here again!

Lux Villa, sunny deck w fire pit, private retreat
There aren’t enough words to describe how perfect this place was. We spent the weekend celebrating a birthday and we couldn’t have asked for a better experience. To start our host Sheryl was very accommodating and proactive of our flexible requests. The shower was out of this world. It was as if the clouds parted and heaven shot down the perfect water pressure to bless us. Everything we could have possibly wanted was there labeled and in a box. The bed was so comfortable and each night it was time to sleep we passed out instantly. The chickens and pool was a beautiful touch that only added to the ambiance of beauty. I got a chance to meet Sheryl randomly and she was super nice and very pet friendly. When we arrived Sheryl acknowledged the celebration by providing a bottle of red wine and premium milk chocolate for us to enjoy. We were truly able to fully let go and relax here
Quick stats about guesthouse rentals in Woodside
Total rentals
20 properties
Nightly prices starting at
G$12,549 GYD before taxes and fees
Total number of reviews
1K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Santa Cruz Beach
- Capitola Beach
- Rio Del Mar Beach
- Golden Gate Park
- Stanford University
- Oracle Park
- Seacliff State Beach
- Twin Peaks
- Bolinas Beach
- Davenport Beach
- Montara State Beach
- Pescadero State Beach
- Twin Lakes State Beach
- Capitola State Beach
- New Brighton State Beach
- Muir Woods National Monument
- Rodeo Beach
- Mission Dolores Park
- China Beach, San Francisco
- Rockaway Beach
- Bonny Doon Beach
- Sumner Beach
- Black Sands Beach
- Joaquin Miller Park