
Guest house holiday rentals in Woodside
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Top-rated guest house rentals in Woodside
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Popular amenities for guest house rentals in Woodside
Family-friendly guest house rentals

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!

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.

Simplistic Crocker Suite
Five stars all around. This was my wife and I's second time staying at Mai's place (the first time being one year ago on our honeymoon!). We love SF, and Mai's place is the perfect respite from the city while remaining relatively close to most areas of interest. Mai is so kind and accommodating, and her place surely does feel like home! We look forward to staying here again and again in the future.

Greenwood Guest House, a Peaceful Oasis
Amy was the perfect host. She was kind and responsive. Great location and beautiful view. We will stay here again!

Little Cottage on the Hill
We thoroughly enjoyed our stay. We were comfortable, slept well, and loved the private and beautiful surroundings

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

La Casita - a quiet studio, Crocker Amazon area!
Very clean, quiet neighborhood, and had everything we needed! Would be happy to stay again.

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!

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.
Katie's place was very comfortable and quiet in a great location with easy access to SCU. It worked perfect for us to enjoy our son's graduation. We would absolutely choose to stay here again.

1-bedroom guesthouse w/ full kitchen near DTSJ/SAP
Amazing cozy house! Thank you for everything!
Guest house rentals with a washing machine 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!

Stylish Spacious Seaside Retreat, Walking to Beach
We had a delightful stay here! It was a great location - easy to walk to the beach and drive downtown. The stay was comfortable, clean, and quiet.

Downtown Campbell Executive Cottage
I felt at home the minute I entered this handsome studio. The layout feels spacious and peaceful, with window and door looking out to a beautiful backyard shared with the hosts (who I never ran into). From the personalized welcome sign with my name on it, to small helpful notes around the unit, I felt welcomed and cared for. (Vs. last place that greeted me w/ list of rules to control my behavior). Very comfortable bed (w/ blanket wrapped in sheets like an upscale hotel--thank you!). Kitchen had everything needed for cooking a few meals. Loved the options for soft lighting in kitchen and bed reading lights. Loved being just a block away from downtown Campbell, with all its restaurants and shops. The whole neighborhood is peaceful and walkable--one of my favorites in the San Jose area. I look forward to staying here again someday!

Private Abodu Guesthouse in Downtown San Jose
Excellent stay as always. Walkable distance into town. Lovely garden to chill out in. Flora always on hand to help out. I love her doggy Honey x

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.

Private Cottage near Redwood City and San Carlos Downtowns
Great experience in every way. Nico was response and friendly. Place was just as described. Would definitely stay 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

🌼Modern guesthouse w private patio and ♨️ hot tub
Ela was so friendly and we felt at home right away. The guest house is perfect for visiting Palo Alto, San Francisco and the bay area. we really enjoyed our stay and will keep this spot in mind for our next visit!
Quick stats about guest house rentals in Woodside
Total rentals
20 properties
Nightly prices starting at
$77 SGD 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