Guesthouse vacation rentals in Woodside

Find and book unique guesthouse rentals on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Woodside guesthouse rentals

Family-friendly guest house rentals

Top guest favorite
Guesthouse in Oakland
4.97 out of 5 average rating, 248 reviews

82 “ Pool, Jacuzzi , HOT SAUNA, VIEWS, Newer ADU!

MariaRating, 5 stars5 days ago
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.
Superhost
Guesthouse in Half Moon Bay
4.82 out of 5 average rating, 507 reviews

Coastal Cabin-outdoor Firepit near Trails & Harbor

JoannRating, 5 stars3 weeks ago
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!
Top guest favorite
Guesthouse in Redwood City
4.98 out of 5 average rating, 424 reviews

Quiet , Private Studio / Cottage

TimRating, 5 stars3 weeks ago
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.
Guest favorite
Guesthouse in Monte Sereno
4.9 out of 5 average rating, 211 reviews

Greenwood Guest House, a Peaceful Oasis

BeckyRating, 5 stars4 weeks ago
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.
Top guest favorite
Guesthouse in Hillsborough
4.95 out of 5 average rating, 918 reviews

Little Cottage on the Hill

KodyRating, 5 stars2 weeks ago
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.
Guest favorite
Guesthouse in Menlo Park
4.97 out of 5 average rating, 150 reviews

Cottage near dwntwn Palo Alto, Stanford, Face-book

LanieRating, 5 stars6 months ago
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!
Guest favorite
Guesthouse in Palo Alto
4.96 out of 5 average rating, 125 reviews

Spacious cottage near downtown & Stanford with AC

FlaviaRating, 5 stars1 month ago
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 :)
Guest favorite
Guesthouse in Sunnyvale
4.96 out of 5 average rating, 429 reviews

Private cottage in a garden

SukuntheaRating, 5 stars3 weeks ago
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

Guest favorite
Guesthouse in Downtown San Jose
4.96 out of 5 average rating, 104 reviews

Cozy Private 1B1B Cottage near Japantown

KathleenRating, 5 stars1 month ago
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!
Top guest favorite
Guesthouse in Los Gatos
5 out of 5 average rating, 127 reviews

Orchard Cottage in convenient countryside location

AlexRating, 5 stars4 days ago
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!
Guest favorite
Guesthouse in San Jose
4.93 out of 5 average rating, 143 reviews

Newly built stylish guesthouse

GloriaRating, 5 stars2 weeks ago
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.
Guest favorite
Guesthouse in Oakland
4.91 out of 5 average rating, 345 reviews

Guesthouse Garden Retreat

MadalynRating, 5 stars2 weeks ago
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!!!
Guest favorite
Guesthouse in Half Moon Bay
4.94 out of 5 average rating, 174 reviews

Boho beach bungalow- walk to Poplar Beach

MoeRating, 5 stars3 weeks ago
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!
Guest favorite
Guesthouse in Palo Alto
4.93 out of 5 average rating, 127 reviews

Palo Alto Cottage: Privacy, Comfort & Convenience

RuoyingRating, 5 stars5 days ago
Host was super friendly and responsive. Highly recommend!
Guest favorite
Guesthouse in Menlo Park
4.93 out of 5 average rating, 221 reviews

Charming, modern, restorative, private studio

ErinRating, 5 stars1 month ago
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!
Guest favorite
Guesthouse in Santa Clara
4.92 out of 5 average rating, 152 reviews

Entire guesthouse Santa Clara smart lock entrance.

RachelRating, 5 stars3 weeks ago
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

Top guest favorite
Guesthouse in Oakland
4.99 out of 5 average rating, 203 reviews

Redwood Heights Cottage with Stunning Bay Views

EsmeraldaRating, 5 stars1 week ago
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!
Guest favorite
Guesthouse in Menlo Park
4.91 out of 5 average rating, 403 reviews

Cottage near downtown Palo Alto

RichardRating, 5 stars5 days ago
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.
Guest favorite
Guesthouse in Half Moon Bay
4.9 out of 5 average rating, 293 reviews

Stylish Spacious Seaside Retreat, Walking to Beach

CynthiaRating, 5 stars2 weeks ago
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.
Guest favorite
Guesthouse in Downtown San Jose
4.98 out of 5 average rating, 208 reviews

Private Abodu Guesthouse in Downtown San Jose

JeffRating, 5 stars2 weeks ago
Excellent stay! Flora was very responsive and friendly. I will be looking for Flora’s place next time I’m in San Jose.
Top guest favorite
Guesthouse in San Jose
4.98 out of 5 average rating, 342 reviews

Private unit close to Santa Clara University

ShoaibRating, 5 stars1 week ago
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.
Guest favorite
Guesthouse in Menlo Park
4.91 out of 5 average rating, 127 reviews

Menlo Park 2 Bedr Cottage

TanyaRating, 5 stars1 month ago
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!!
Guest favorite
Guesthouse in Sunnyvale
4.89 out of 5 average rating, 274 reviews

Tranquil and Charming 1-Bedroom Guest house w/bath

LillianRating, 5 stars1 week ago
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!
Top guest favorite
Guesthouse in Sunnyvale
4.99 out of 5 average rating, 223 reviews

Lux Villa, sunny deck w fire pit, private retreat

Matthew LawrenceRating, 5 stars1 week ago
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

Destinations to explore