Holiday houses in Hillsborough

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Top-rated holiday rentals in Hillsborough

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Guest suite in San Mateo

4.92 out of 5 average rating, 332 reviews

San Mateo Getaway Private 2 Bedroom

Bright & spacious 2 bedroom apartment with beautiful backyard in San Mateo. In-law apartment with private entrance dedicated to hosting guests. Located in quiet residential neighborhood, but close to activities for families and singles. Amenities include wet bar area with toaster oven, coffee maker, mini fridge and microwave! Laundry available upon request. Easy access to San Francisco/San Jose via 280 & 101. Close to SFO, Cal train/BART and Downtown San Mateo. Lots of street parking.

Guest favourite

Apartment in San Mateo

4.94 out of 5 average rating, 212 reviews

Fabulous apartment in downtown San Mateo

Relax away from the hustle of the city in your apartment in downtown San Mateo. Located only two blocks from the San Mateo Caltrain, you can get to or from SF or SJ in 30 minutes. Our home has a separate entrance for the guest apartment on the second floor. Tuck yourself away in the California King sized bed, or explore downtown on foot. With over 100 restaurants in walking distance, you will not have a shortage of delicious dining. Eat out or enjoy a meal in the comfort of your home. Welcome!

Top Guest favourite

Guesthouse in San Carlos

4.99 out of 5 average rating, 725 reviews

Private Garden Cottage

Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.

Guest favourite

Home in Millbrae

4.9 out of 5 average rating, 354 reviews

3 Bedroom Entire House @ Safe Town in SFO Bay Area

Our Airbnb house is located in the beautiful Millbrae town. Your family will be close to everything when you stay at this centrally-located place. Walkable distance to locale restaurants, coffee shops and supermarket. With 3 Bedrooms, newly updated 2 bathrooms, a full kitchen and the backyard, heating, A/C, TV, wi-fi, your family will enjoy a cozy stay with urban suburban mix feel. Easily get on Freeway 101, 280, 15 minutes driving to SFO Airport. 10 minutes to Bart, Caltrain Station.

Guest favourite

Guest suite in Belmont

4.94 out of 5 average rating, 142 reviews

Cozy private in-law suite, close to SFO, fast WiFi

Newly renovated, spacious in-law unit in the Belmont hills with a private entrance and Bay views. This adorable space is cozy and great for a weekend respite or remote work. SFO airport is just 15 mins away. Close by Stanford and San Carlos. Short drive to hiking trails and 30 mins away from the Pacific ocean. Easy access to San Francisco and San Jose, via freeway 101, 280, and 92. 🌞 Solar-powered through the day with battery 🔋 back-up at night. No outages and eco-friendly. 🌲

Guest favourite

Home in Burlingame

4.92 out of 5 average rating, 178 reviews

Cozy Modern Craftsman Retreat

Private studio with a large outdoor patio. Just a short walk to the dinning and shopping on Burlingame Avenue and also on historic Broadway. Caltrain and Bart are minutes away to get take you to wherever you need to go. Fast wifi and espresso maker provided. Enjoy fresh fruit from our orange tree, and a rosemary bush for those that enjoy cooking. Relax with our large queen bed, recessed dimmable lighting and a large flat panel 4K smart TV w/apps for Netflix, Amazon Video, etc.

Guest favourite

Guesthouse in San Mateo

4.99 out of 5 average rating, 164 reviews

Modern guest house in great location

Private 1 bedroom + 1 bathroom with your own entrance. Highlights: • self-checkin with code on digital lock • free parking + additional free street parking • professional cleaning and sanitizing • king size bed with premium mattress and linens • located at end of cul-de-sac in a safe and quiet neighborhood • standing desk with monitor and docking station • high speed WiFi • 55” smart TV • Rainfall shower, bidet toilet with heated seat, heated towel rack, makeup mirror

Guest favourite

Home in San Mateo

4.94 out of 5 average rating, 124 reviews

Modern Mid-Century Retreat • Quick Access to SFO

Close to San Francisco, SFO and the Peninsula. Step into this stunning 1956 Joseph Eichler-designed home, updated in 2017 to preserve its mid-century charm with modern touches. The enclosed atrium, featuring a custom mural and red maple tree, sets a serene tone upon entry. Inside, you'll find mid-century furniture and art, with a spacious open-concept living area, wood-burning fireplace, dining room, and a fully equipped kitchen—perfect for small gatherings.

Guest favourite

Guest suite in San Mateo

4.93 out of 5 average rating, 247 reviews

Luxury King Bed & Spa Bathroom

Our spacious guest suite has its own private entrance, comfortable pillow-top king size bed, work-friendly laptop desk, hi-speed wifi, spa bathroom with heated floor, mini fridge, microwave and a Keurig coffee maker. The guest suite is part of the main home, but there are no shared spaces and the areas are separated by a locked solid wood door & noise-dampening cushions. Our guest suite is ideal for couples visiting family in the neighborhood.

Top Guest favourite

Guesthouse in San Mateo

4.93 out of 5 average rating, 225 reviews

Charming Private Quiet Backyard Studio

This charming, sunny, secluded backyard studio is located in the heart of San Mateo, near public transportation, freeways, restaurants, shopping, and 15 minutes to SFO. Private entrance, quiet backyard setting, plenty of street parking. Less than a 5-min walk to Safeway, CVS, Starbucks and restaurants. * To my regular guests, the rate increase is due to SM County increasing the tax rate. *

Top Guest favourite

Guesthouse in Hillsborough

4.95 out of 5 average rating, 919 reviews

Little Cottage on the Hill

Enjoy a peaceful stay at this charming, secluded detached garden cottage great for a stay-cation or as a work-from-home alternative. Due to the coronavirus, we are taking extra care to disinfect frequently touched surfaces between reservations. The cottage features a queen-sized bed, a fireplace, private bathroom and kitchenette. Perfect for both leisure and Business travelers.

Top Guest favourite

Guesthouse in Burlingame

4.98 out of 5 average rating, 320 reviews

Clean&Cozy Cottage near downtown Burlingame & SFO

Our sunny backyard cottage, with outdoor private entry, is centrally located in Burlingame between Burlingame Avenue and Broadway and is a great spot suited to a business traveler in search of a home away from home while also being ideal for vacationers looking to live like a local, only miles from SF. Enjoy and unwind!