Holiday houses in Hillsborough

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Top-rated holiday rentals in Hillsborough

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Guest favourite

Guesthouse in San Carlos

4.99 out of 5 average rating, 584 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.

21–28 Jun

$266 NZD per night

Guest favourite

Guesthouse in Belmont

4.97 out of 5 average rating, 362 reviews

A Comfortable & Private Guest House

Attn: Promo Rate for Health Care Workers & First Responders on stays of ONE week, or more. Please alert us, so that we can offer you a promo rate. In light of these uncertain times, rest assured that we are doing everything to ensure the safety of our guests. Beautiful, Secluded, Safe, Fully Stocked, Comfortable, Newly Renovated, & Close to Public Transportation. In the heart of Silicon Valley with its own private entrance. It's 30 mins. N of San Jose, and 30 mins. S of San Francisco.

5–12 Nov

$203 NZD per night

Guest favourite

Guest suite in Belmont

4.95 out of 5 average rating, 101 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. 🌲

12–19 Aug

$208 NZD per night

Guest favourite

Home in Burlingame

4.91 out of 5 average rating, 148 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.

22–29 Dec

$299 NZD per night

Superhost

Guesthouse in San Mateo

4.92 out of 5 average rating, 145 reviews

Cozy Studio 1B/1B w A/C No Pet in San Mateo

This cozy studio is good for a couple vacation. It is also suitable for business trip with high speed WIFI. It is well equipped with all the amenities you need to enjoy your stay! 15 minutes walk to San Mateo Downtown. 11 minutes walk to Cal Train Station, which takes you to San Francisco in 30 min, and San Jose 45 min. If you have a car, you can reach those popular destinations easily: Hwy 101: 3 min San Francisco Airport: 9 min Apple Palo Alto: 12 miles Stanford: 17 miles

2–9 Oct

$222 NZD per night

Guest favourite

Home in Belmont

4.93 out of 5 average rating, 324 reviews

Hidden French Gem ~ near Caltrain, SFO

Highly welcome respectful travelers to step through the 750ft super quiet European-style private studio with secluded bay view. Curl up in front of the 4K TV for movie nights at this stylish, soundproofed nest with a luxury mattress, washer and dryer! — welcome infant & kids. — Read everything to avoid surprises. — 5 min walks to park, Caltrain/restaurants; 10~13 min drive to SFO/Stanford; 20-25 min SF. — No pets, no smoking/vaping, no party! — book for 3 if need single bed

4–11 Aug

$267 NZD per night

Guest favourite

Cottage in San Mateo

4.95 out of 5 average rating, 465 reviews

Entire Private Studio by SFO, AC/Heat/Free Parking

Entire cottage with private entrance. * self check-in with codes * free parking on driveway * AC & heating * 1 queen bed, 1 sofa (converts into twin bed) * fiber speed WiFi * kitchenette with sink, dishes & utensils, microwave, oven, mini fridge, keurig coffee maker, water boiler, NO STOVE * 15 min drive to SFO * 10 min walk to Caltrain * walking distances to restaurants, bars & groceries * located at end of cul de sac in a safe & quiet neighborhood * TV with Chromecast

4–11 Jul

$307 NZD per night

Guest favourite

Guest suite in El Granada

4.97 out of 5 average rating, 213 reviews

Cozy, creekside guest suite with private entrance

Cozy, creekside guest suite just blocks from the beach and the picturesque harbor. This one bedroom unit has been completely remodeled with a fully stocked kitchen, a separate eating/work space and a bathroom with a walk in shower. Drink your morning coffee (host provided) on the furnished deck while listening to the sounds of the running creek and the fog horn in the distance. This unit has its own private entrance and is closed off from the rest of the house.

29 Sep – 6 Oct

$277 NZD per night

Superhost

Guesthouse in San Mateo

4.84 out of 5 average rating, 160 reviews

Charming cozy studio King-sized bed

Hi there! Welcome to our cozy studio in the heart of the bay area. You'll find yourself conveniently located to downtown San Mateo and all the transportation. This is a shared walkway, private studio. The unit has 1 king sized bed with ample pillows. Included are fast wifi, 43" TV, Netflix, coffee, full kitchenette for light cooking. Self-check in. No central heat, no AC unit. Equipped with space heater

24–31 Dec

$268 NZD per night

Guest favourite

Guesthouse in San Mateo

4.93 out of 5 average rating, 193 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. *

22–29 Sep

$243 NZD per night

Guest favourite

Guesthouse in Hillsborough

4.95 out of 5 average rating, 807 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.

15–22 Dec

$239 NZD per night

Superhost

Guesthouse in Belmont

4.84 out of 5 average rating, 202 reviews

Charming Cottage Studio

Our place is small but comfy for solo adventurers and business travelers. Very safe neighborhood. Is close to public transportations CalTrains station, bus stops, restaurants and malls. Plenty of parking on the street. We are 30 min to San Jose, and 30 min to San Francisco. Very close to Oracle and to the 101 & 92 Highways. Only 20 min to the Ocean in Half Moon Bay.

13–20 Jul

$172 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Hillsborough holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Hillsborough's top sights

Limon Rotisserie Burlingame8 locals recommend

Crepevine14 locals recommend

RASA11 locals recommend

Copenhagen Bakery & Cafe24 locals recommend

Mingalaba Restaurant28 locals recommend

Sawyer Camp Trail54 locals recommend

Other great holiday rentals in Hillsborough

Guest favourite

Guest suite in San Mateo

4.94 out of 5 average rating, 205 reviews

Luxury King Bed & Spa Bathroom

28 Jun – 5 Jul

$401 NZD per night

Guest favourite

Guesthouse in Pacifica

4.98 out of 5 average rating, 368 reviews

NEW Private Studio! Close to SF/SFO/Beach Sanitize

11–18 Sep

$251 NZD per night

Guest favourite

Home in Moss Beach

4.92 out of 5 average rating, 108 reviews

Studio with Private Entrance / Patio / Hot Tub

30 Jan – 6 Feb

$267 NZD per night

Superhost

Home in Half Moon Bay

4.9 out of 5 average rating, 133 reviews

Luxury Beachfront Penthouse Walk to the Beach

30 Jan – 6 Feb

$1,713 NZD per night

Guest favourite

Guest suite in Emerald Hills

4.92 out of 5 average rating, 146 reviews

Elegant retreat in Redwood City

6–13 Dec

$257 NZD per night

Guest favourite

Condo in Hillsborough

5.0 out of 5 average rating, 8 reviews

Breathtaking View Modern 1b1b on Top of the World

9–16 Sep

$291 NZD per night

Guest favourite

Guest suite in Burlingame

4.85 out of 5 average rating, 85 reviews

Gorgeous Suite close to SFO Airport, Self Check-In

14–21 Jun

$275 NZD per night

Guest favourite

Guest suite in Belmont

4.93 out of 5 average rating, 80 reviews

New, modern quiet private studio

16–23 Aug

$241 NZD per night

Show all

Quick stats about holiday rentals in Hillsborough

Total rentals	200 properties
Rentals with dedicated workspaces	100 properties have a dedicated workspace
Rentals with a pool	20 properties have a pool
Pet-friendly rentals	40 properties allow pets
Family-friendly rentals	60 properties are a good fit for families
Total number of reviews	6K reviews

Holiday houses in Hillsborough

Top-rated holiday rentals in Hillsborough

Guesthouse in San Carlos

Guesthouse in Belmont

Guest suite in Belmont

Home in Burlingame

Guesthouse in San Mateo

Home in Belmont

Cottage in San Mateo

Guest suite in El Granada

Guesthouse in San Mateo

Guesthouse in San Mateo

Guesthouse in Hillsborough

Guesthouse in Belmont

Holiday rentals for every style

Apartments

Houses

Hotels

Popular amenities for Hillsborough holiday rentals

Stay near Hillsborough's top sights

Other great holiday rentals in Hillsborough

Guest suite in San Mateo

Guesthouse in Pacifica

Home in Moss Beach

Home in Half Moon Bay

Guest suite in Emerald Hills

Condo in Hillsborough

Guest suite in Burlingame

Guest suite in Belmont

Quick stats about holiday rentals in Hillsborough

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore