Cabin holiday rentals in San Mateo

Private Guest-House in the Redwoods

Our custom built guesthouse was completed in 2016. It is situated on 5 redwood-covered acres, 10 minutes south of Los Gatos and 20 minutes from Santa Cruz. We have easy access to hiking and biking trails, world-class wine-tasting, microbreweries, shops, amazing dining, and more! There is something for everyone in our area! We are surrounded by a 35 acre tree farm, so it's very private, yet close to the silicon valley! Our property has a standby generator so we are not affected by power outages.

Surfer’s Perch, rustic cabin overlooking the ocean

A unique and tranquil getaway on the Bolinas mesa overlooking the Pacific ocean. Our 1940's small hand-built cabin is located one house in from the end of a dirt road, and the builder's family still calls it home. A rustic and cozy place with everything you need, a launchpad for you to connect with nature & a gorgeous view to Stinson Beach. Enjoy watching the wildlife: deer, raccoons, quail & many birds that enjoy the yard right outside the window and follow the rhythm of the rising sun & moon.

King Suite Cabin | Santa Cruz Mountains

Experience the majesty of the Santa Cruz Mountains. Starting with a relaxing king bed suite and clawfoot tub, this unique and tranquil mountain retreat is nestled among the redwoods only a short drive from Santa Cruz. Find yourself cozy by a fireplace, relaxing under a gazebo, or doing yoga overlooking the redwoods. Location is a hikers paradise as it backs up to lower Castle Rock and Big Basin National Park and many of the best hiking trails in the Santa Cruz Mountains. Kid and pet friendly.

Creekside Cabin

Step into the charm an 1880s lumberjack cabin in the heart of Mill Valley, just steps from downtown. This peaceful hideaway has been decorated artistically, and sits alongside the audible flow of Mill Valley Creek. Inside is a Tea/Zen Room for relaxation, an office for productivity, a deck surrounded by redwoods, and two cozy bedrooms. Perfect for unwinding or focusing, the cabin offers historic character, modern comforts, and a tranquil setting to recharge and inspire. It’s a special spot. ✨

Peaceful Writer’s Cabin in Marin

Escape to a peaceful retreat tucked in the trees near China Camp. This cozy cabin is a sanctuary for writers & artists. Reconnect in the private outdoor sauna and cold plunge, then spend some time on your manuscript, before an evening mountain bike ride. Just minutes from coastline trails, this cabin offers quiet seclusion and easy access to the natural beauty of Marin. Whether you're planning a solo writing weekend or a digital detox, this is your place to pause, create, and be inspired.

Either Way Hideaway

Relax and enjoy riverside views in our tranquil Santa Cruz Mountains guesthouse. Cozy by our fire pit, take a dip in a private hot tub and enjoy the sounds of the river flow by. Hike Big Basin, Castle Rock and Henry Cowell State Parks. Close to historic downtown Boulder Creek and the Santa Cruz boardwalk, it’s the perfect base for exploring Santa Cruz county. Immerse yourself in of nature while staying connected and comfortable. Either way, you’ll enjoy your stay! SCC Permit #251382

Guesthouse in woodside -

This private guest house is located on one of the most prestigious properties in Woodside with it's own private entrance & setting on a 1.5 acre lot. Includes living room, 1 queen bedroom, sofa bed, kitchen and private patio - * There are 15 stairs from where the car is parked to the guest house. Access to basketball court and play structure. No access to the pool/hot tub/fire pit. Close to restaurants, 2 mins from 280 HW, 3 mins to downtown Woodside, 10 mins to Stanford University.

Wit's End, Stinson Beach

The best rental in all Stinson Beach! Read the reviews! 3 bedroom beach house. Brightly lit and professionally decorated. 5 houses to the beach down the lane, 25 yards from a surfboard rental shop and 300 yards from "downtown" Stinson Beach. Central air and heat. Huge outdoor area with firepit. Walk to everything: the market, restaurants, beach, etc. Hot tub. Dog friendly. No better place! Ask us about our rock and roll history, you’ll be Grateful you did…

Hike-in Bay Views Cabin w HotTub

Hike up to a well designed, small-but-mighty modern cabin with fast WiFi, your own hot tub and a panoramic view spanning across the bay from the Golden Gate to the San Mateo bridge. 108 stairs lead up to the Aerie, so if you don’t want to get your steps in, this is probably not the space for you! 15 min from OAK and city life, but a world away. Sunsets are glorious here. The Aerie is a special spot just for 1 or 2, so leave the posse behind. Registered guests only.

Edge of the Redwoods, cozy cabin retreat

Come enjoy the redwoods at this cozy, cabin retreat on a flower farm in La Honda! We are located 30 minutes from 280. 5 minutes from the famous Alice’s Restaurant - great food, great music, great company. 6 minutes from the neighborhood bar, Apple Jack’s - bbq and live music! 15 minutes from world class surfing, beaches, and hiking. Come relax and unwind at The Edge of the Redwoods!

Private Cabin by Lake Merritt

Backyard cabin steps away from Lake Merritt and Grand Avenue restaurants and businesses. Very quiet and cozy space for singles and couples, the cabin can work for 3 or 4 close friends who are very comfortable with sharing space .Convenient to public transportation, easy commute to San Francisco or Berkeley. Located behind our home . 400 square foot cabin with sleeping loft.

Epic Santa Cruz Mountain Views in Rustic Home

Located behind Los Gatos in the Santa Cruz Mountains, this unique property features a stunning view of the Mountains looking West towards the Pacific Ocean. On most days a sliver of the ocean is visible or the marine layer that often blankets the coastline. A 15 min drive to Downtown Los Gatos. With 3 bedrooms and 2 baths we can support up to 7.