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Guesthouse vacation rentals in Woodside

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Woodside guesthouses

Family-friendly guesthouses

Guest favourite
Guesthouse in Oakland
4.95 out of 5 average rating, 209 reviews

Charming Cozy Cottage in Eco-Garden Oasis

AdrienneRating, 5 stars3 months ago
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!
Guest favourite
Guesthouse in Palo Alto
4.77 out of 5 average rating, 164 reviews

Sunnystay: Bright Garden Palo Alto Studio Cottage

PatriciaRating, 5 stars17 months ago
Superb location for walking to Univ Ave restaurants. Lovely neighborhood for walking. Quiet. Short drive to med ctr. Personable hosts.
Guest favourite
Guesthouse in Monte Sereno
4.9 out of 5 average rating, 208 reviews

Greenwood Guest House, a Peaceful Oasis

RobertRating, 5 stars1 month ago
The lodging is in the back, in a garden and near the swimming pool and tennis court. The backdrop is beautiful, and the host and hostess were friendly and accommodating. There is privacy and the area offers much in terms of restaurants and shopping. The internet is broadband, so one can work in the lodging. Amy and Lou are wonderful people----worthy of friendship in any circumstance.
Top guest favourite
Guesthouse in Hillsborough
4.95 out of 5 average rating, 911 reviews

Little Cottage on the Hill

LydiaRating, 5 starstoday
Very pleasant and well-maintained accommodation. Everything has been thought of. Video is also very fun. Radhia was always quick to answer questions. We'll be back next week with great pleasure.
Guest favourite
Guesthouse in Menlo Park
4.97 out of 5 average rating, 150 reviews

Cottage near dwntwn Palo Alto, Stanford, Face-book

LanieRating, 5 stars4 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!
Superhost
Guesthouse in Monte Sereno
4.84 out of 5 average rating, 160 reviews

Private Cozy Suite Los Gatos - Saratoga

MicheleneRating, 5 stars3 weeks ago
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.
Superhost
Guesthouse in Willow Glen
4.87 out of 5 average rating, 172 reviews

Modern 2Bed/1Bath suite in San Jose

RuthRating, 5 stars2 months ago
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.
Guest favourite
Guesthouse in Redwood City
4.88 out of 5 average rating, 597 reviews

Charming cottage, walk to Caltrain

WhitneyRating, 5 stars4 weeks ago
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!

Guesthouses with a patio

Top guest favourite
Guesthouse in Los Gatos
5 out of 5 average rating, 121 reviews

Orchard Cottage in convenient countryside location

RamonaRating, 5 stars2 weeks ago
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!
Guest favourite
Guesthouse in San Jose
4.94 out of 5 average rating, 130 reviews

Newly built stylish guesthouse

BrettRating, 5 stars3 weeks ago
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.
Top guest favourite
Guesthouse in San Carlos
4.99 out of 5 average rating, 102 reviews

Delightful Hideaway in San Carlos

TerryRating, 5 stars1 week ago
Cute Airbnb in a pretty neighborhood, not too far from freeways if you're going for work. Street parking is easy. Lots of privacy. Unit is located above the garage so no need to worry about hearing the folks who live there or them hearing you. Loved the deck overlooking the garden. Enjoyed that every day after long days of meetings. Marilynn responded so quickly and was really helpful. The trees and flowers in the neighborhood were beautiful. Would definitely stay here again.
Guest favourite
Guesthouse in Half Moon Bay
4.93 out of 5 average rating, 168 reviews

Boho beach bungalow- walk to Poplar Beach

MariahRating, 5 stars3 weeks ago
Very cozy and private. I brought my family of four and we had a lovely time. The only tricky part is figure out how to lock the door, but if that’s the worst of it, then I’d say it was pretty amazing. It’s about a 15 minute walk to the beach along nature paths and side streets. Definitely worth it!
Guest favourite
Guesthouse in Palo Alto
4.93 out of 5 average rating, 120 reviews

Palo Alto Cottage: Privacy, Comfort & Convenience

LeonardRating, 5 stars3 days ago
Had a short 2 night stay at this lovely cottage space. Everything as shown in pictures and described in the details. The style and feel of the space left us right as room for a good rest after international travel. I would absolutely recommend this to my friends I'm staying in the area.
Guest favourite
Guesthouse in Menlo Park
4.93 out of 5 average rating, 213 reviews

Charming, modern, restorative, private studio

VinceRating, 5 stars2 weeks ago
Just as promised, clean and comfortable. thanks
Top guest favourite
Guesthouse in San Carlos
4.99 out of 5 average rating, 138 reviews

Silicon Valley Oasis

StephanieRating, 5 stars2 weeks ago
We felt right at home in this cozy Air bnb. The garden areas surrounding the property are beautiful. We had everything we needed and more in the kitchen where we made breakfast every morning. Lots of cookware and cabinet full of spices. Super clean. Bed was comfortable. Walking distance to downtown San Carlos was about 23 minutes. The host checked in regularly with us online and we appreciated the attention. Was sad to leave when our time was up. We hope to return as we have family in the area.
Top guest favourite
Guesthouse in San Jose
4.99 out of 5 average rating, 170 reviews

1-bedroom guesthouse w/ full kitchen near DTSJ/SAP

GraceRating, 5 stars2 weeks ago
This place was spotless, and was a nice, private unit with a view of their beautiful garden. Instructions that were given were very detailed and easy to follow, and even had videos where applicable that were helpful. The area is quiet and peaceful, but still very convenient for getting around in San Jose.

Guesthouse rentals with a washer and dryer

Guest favourite
Guesthouse in Evergreen
4.92 out of 5 average rating, 311 reviews

Evergreen Valley Hillside retreat

AudreyRating, 5 stars1 week ago
Really great stay! 10-15 mins away from downtown. Thanks for hosting us!
Guest favourite
Guesthouse in Scotts Valley
4.93 out of 5 average rating, 130 reviews

The Hen House Haven

EliRating, 5 stars4 days ago
What a find! Right where we needed to be and the place was equipped with all the goods. Stove and oven to make dinner, washer and dryer in case you need it! Thanks for hosting
Guest favourite
Guesthouse in Downtown San Jose
4.96 out of 5 average rating, 102 reviews

Cozy Private 1B1B Cottage near Japantown

EmilyRating, 5 stars1 month ago
Stayed at Arthur’s to attend a SAP Center event. Planned to Uber but found the neighborhood very walkable. Place is nicely tucked away and quiet away from the street and main house. We only had trouble street parking on our first night which was a Thursday after 5pm. Otherwise it was fine. Overall enjoyed our stay.
Top guest favourite
Guesthouse in Willow Glen
4.99 out of 5 average rating, 200 reviews

TheStudio in Willow Glen (San Jose) CA-95125

CalebRating, 5 stars3 weeks ago
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!
Guest favourite
Guesthouse in Redwood City
4.96 out of 5 average rating, 24 reviews

Easy commute Private guest suite

ArthurRating, 5 stars2 months ago
Helen's place is roomy with a well-equipped kitchen and a nice bathroom. The dishwasher and washer/dryer provided added convenience. The location is just off busy Woodside Road with a Safeway market about 5 minutes away on foot.
Guest favourite
Guesthouse in Campbell
4.93 out of 5 average rating, 165 reviews

Private Entry Adorable 1 bed 1 bath

ChristineRating, 5 stars2 weeks ago
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!!
Guest favourite
Guesthouse in South San Jose
4.98 out of 5 average rating, 130 reviews

2Bd/1Ba NEW Guest House in S San Jose (w/ Parking)

ITEightRating, 5 stars1 month ago
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.
Guest favourite
Guesthouse in Sunnyvale
4.89 out of 5 average rating, 261 reviews

Tranquil and Charming 1-Bedroom Guest house w/bath

GregRating, 5 stars1 week ago
Very nice to find a affordable place to stay With my schnauzer Winston. He is a low impact dog (doesn't shed, well behaved), but most charge more regardless. The local area has lots of places open late, which turned out a boon for me as I work as a stage manager and get home after 10p. Many thanks Margret and David!

Quick stats about guesthouse rentals in Woodside

  • Total rentals

    20 properties

  • Nightly prices starting at

    $84 CAD 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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