Vacation rentals in Hillsborough

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Top-rated vacation rentals in Hillsborough

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

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Guest favourite

Guesthouse in Belmont

4.97 out of 5 average rating, 363 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.

Jan. 23 – 30

$167 CAD 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. 🌲

Jun. 27 – Jul. 4

$179 CAD 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.

Sep. 28 – Oct. 5

$243 CAD 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

Sep. 16 – 23

$180 CAD per night

Guest favourite

Home in Belmont

4.93 out of 5 average rating, 323 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

Aug. 1 – 8

$217 CAD 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

Sep. 23 – 30

$249 CAD 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.

Sep. 10 – 17

$225 CAD per night

Guest favourite

Home in Montara

4.97 out of 5 average rating, 273 reviews

A private beachy pad in Montara

Welcome to Chez Sage! Your own private apartment get-away, with a private deck and ocean views, is just 30 minutes south of San Francisco. The entrance to your private apartment leads you up the stairs to a deck with an ocean peek. Enter your home away from home and relax in the window seat to gaze at Montara Mountain or eat breakfast on the island with peeks of the ocean. Once you're settled, it's just a short stroll to watch the sunset from the beach.

Jul. 10 – 17

$232 CAD per night

Guest favourite

Guest suite in San Mateo

4.94 out of 5 average rating, 206 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.

Jun. 10 – 17

$266 CAD per night

Superhost

Guesthouse in San Mateo

4.84 out of 5 average rating, 161 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

Mar. 17 – 24

$236 CAD 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. *

Sep. 25 – Oct. 2

$197 CAD per night

Guest favourite

Guesthouse in Hillsborough

4.95 out of 5 average rating, 809 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.

Jul. 31 – Aug. 7

$199 CAD per night