Hillsborough vacation rentals

We found 34 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Hillsborough to find one that's perfect for your trip. Whether you’re staying in a vacation home with your kids or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. Whatever you're looking for, you'll be able to choose a rental to meet everyone's needs, including accessible or non-smoking choices.

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Find out more about Hillsborough

Find out more about Hillsborough

Why visit Hillsborough

  1. Outdoor Adventures: Enjoy a variety of outdoor activities in the beautiful parks and nearby beaches, perfect for adventure enthusiasts.
  2. Scenic Beauty: Experience stunning landscapes and picturesque neighborhoods, particularly in the Highlands area.
  3. Cultural Experiences: Explore the local art scene and historic colleges that enrich the area's cultural fabric.
  4. Family-Friendly Atmosphere: Hillsborough offers a welcoming environment with activities suitable for all ages.
  5. Variety of Accommodations: Choose from cozy apartments to spacious vacation homes tailored to your needs.

Popular types of accommodation around Hillsborough

Planning a getaway to Hillsborough? You're in for a treat! Discover the best vacation rentals, including cozy apartments, spacious private homes, and convenient apart-hotels. Whether you're looking for a charming Hillsborough house, a stylish townhouse, or a modern apartment, you’ll find the perfect spot to relax and recharge. Explore your options and make your stay unforgettable!

  • Apartments: The top choice for vacation rentals in Hillsborough, offering a blend of comfort and convenience for solo travelers or families.
  • Houses: A popular option, these homes provide ample space and privacy for groups or families seeking a home-like atmosphere.
  • Cottages: Charming and cozy, cottages are perfect for those looking for a quaint getaway in a peaceful setting.
  • Condos: Offering modern amenities and often situated in prime locations, condos are a favorite for travelers seeking convenience.
  • House Boats: A unique experience, house boats allow you to enjoy a stay on the water while exploring the beautiful coastline.**

Top attractions around Hillsborough

Hillsborough, California, is ideal for outdoor and adventure enthusiasts, offering stunning scenery and a range of activities. Visitors can explore urban parks, nearby beaches, and historic colleges and universities. The area's attractions cater to those seeking cultural experiences and family-friendly outings, ensuring a memorable vacation for everyone. Enjoy the natural beauty and rich history that Hillsborough has to offer!

  1. San Francisco Bay: Located 8 miles from Hillsborough, this vibrant neighborhood offers stunning waterfront views, bustling city life, and a variety of recreational activities, from sailing to picnicking along the shoreline.
  2. San Mateo County Event Center: Just 5 miles away, this venue is perfect for business events, exhibitions, and conventions, providing modern facilities and a professional atmosphere for networking and collaboration.
  3. Stanford University: Situated 15 miles from Hillsborough, this historic university features beautiful architecture, expansive gardens, and rich cultural experiences, including museums and art galleries.

Things to do recommended for couples

For a romantic getaway in Hillsborough, enjoy a concert at the Bill Graham Civic Auditorium, indulge in relaxation at the Oceanic Foot Spa, or embark on an adventurous day at the University of Surfing. Each experience offers a unique blend of entertainment, wellness, and outdoor fun.

Things to do recommended for families

Families visiting Hillsborough can enjoy an adventurous day at GoKart Racer, just 2 miles away, before indulging in sweet treats at See's Candies, located 5 miles away. For sports enthusiasts, the Chase Center offers exciting events and is 13 miles from Hillsborough, providing a vibrant atmosphere.

Things to do recommended for groups

Experience a day of outdoor fun at Crystal Springs Golf Course, just 1 mile from Hillsborough. Enjoy shopping and family entertainment at Millbrae Square Shopping Center, 2 miles away. For a cultural evening, catch a show at the Orpheum Theatre, located 14 miles from your base.

What do I need to keep in mind when booking a vacation around Hillsborough

When traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Hillsborough with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group activities. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Hillsborough with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Hillsborough: For many, a family vacation wouldn’t be the same without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Hillsborough: If you're searching for vacation rentals that offer discounts for stays of a month or more, you've come to the right place. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay around Hillsborough

Hillsborough, California, offers a delightful blend of outdoor adventures and scenic beauty. Nestled in the heart of Northern California, this charming town features family-friendly neighborhoods, including the picturesque Highlands area. Explore nearby Burlingame for its vibrant urban atmosphere, art scene, and welcoming community. Whether you're looking for stunning homes or simply enjoying the stunning landscapes, Hillsborough provides an unforgettable vacation experience for all types of travelers.

  • San Francisco: Situated approximately 14 miles from Hillsborough, San Francisco is a vibrant city known for its iconic landmarks and diverse culture. Visitors flock to experience its bustling atmosphere, rich history, and stunning outdoor spaces. Explore the famous Golden Gate Park, indulge in shopping at Union Square, or catch a show at one of the many theaters. Don't miss the chance to visit Alcatraz Island or stroll along Fisherman’s Wharf, where you can enjoy fresh seafood and picturesque bay views.
  • Burlingame Hills: Just 0.6 miles from Hillsborough, Burlingame Hills offers a serene retreat with beautiful scenery and outdoor activities. This charming neighborhood is perfect for those looking to escape the hustle and bustle. Enjoy leisurely walks or hikes in the nearby parks, or take in the stunning views of the bay. The local tourist precinct is filled with quaint shops and cafes, making it an ideal spot to relax and unwind while soaking in the picturesque surroundings.
  • Easton Addition: Located a mere 0.7 miles from Hillsborough, Easton Addition is an inviting neighborhood that caters to sports enthusiasts and adventure seekers. With easy access to recreational areas, visitors can partake in a variety of outdoor activities, from hiking to biking. The area also features sports facilities and is close to a national state park, offering ample opportunities for exploration and adventure. Experience the local community and enjoy the vibrant atmosphere as you engage in outdoor fun.

Best time to go to Hillsborough

If you're planning a trip to Hillsborough, it's a good idea to check both the weather and property rates. The warmest month is September. Peak season runs from March to May, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January51.4°F (10.8°C)Light RainMostly SunnyAverageSlightly Low
February52.2°F (11.2°C)Light RainMostly SunnyAverageSlightly Low
March53.4°F (11.9°C)Light RainMostly SunnyHighAverage
April55.8°F (13.2°C)No Rain (Dry)Mostly SunnyHighAverage
May58.1°F (14.5°C)No Rain (Dry)SunnyHighSlightly High
June62.1°F (16.7°C)No Rain (Dry)SunnyAverageSlightly High
July63.1°F (17.3°C)No Rain (Dry)SunnyAverageSlightly High
August64.2°F (17.9°C)No Rain (Dry)SunnyAverageAverage
September64.9°F (18.3°C)No Rain (Dry)SunnyAverageAverage
October62.6°F (17.0°C)No Rain (Dry)SunnyLowSlightly Low
November56.1°F (13.4°C)No Rain (Dry)Mostly SunnyLowAverage
December51.3°F (10.7°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming trip? One effective strategy is to remain flexible with your travel dates, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash™ on your entire booking. Being the planner truly has its benefits! When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash™ on qualifying reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, and easily manage your travel arrangements. You can find all the properties you’ve saved and booked neatly organized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Frequently asked questions

What is the most popular type of vacation rental in Hillsborough?
In Hillsborough, vacation houses are the most popular type of vacation rental, with several available throughout the area. These properties typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and private outdoor spaces, ideal for families or groups looking for comfort and privacy. Nestled in this affluent community, many homes offer scenic views and are conveniently located near parks and recreational areas, providing a serene getaway while still being close to local attractions.
How much does it cost to rent a vacation home in Hillsborough?
Prices for vacation rentals in Hillsborough vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Hillsborough to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Hillsborough vacation house rentals?
You can find great discounts on house rentals in Hillsborough on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Hillsborough?
In Hillsborough, popular rental amenities include fully equipped kitchens, private pools, and hot tubs, making them ideal for travelers seeking comfort and relaxation. Many vacation rentals also feature coffee and tea makers, allowing guests to enjoy warm beverages at their convenience.
Are there any family house rentals in Hillsborough?
In Hillsborough, California, there are several family-friendly house rentals available, making it a great choice for those traveling with children. This upscale community is known for its spacious homes and lush landscapes, providing plenty of room for families to relax and enjoy their stay. Many properties feature large backyards, superb for outdoor play, as well as fully equipped kitchens where families can prepare meals together.

Visitors will appreciate the comfortable living areas, often designed for family gatherings, along with amenities such as Wi-Fi and multiple bedrooms to accommodate everyone. The town's proximity to nearby attractions, including the beautiful parks and recreational areas, adds to its appeal.
Can I rent a vacation home with a pool or hot tub in Hillsborough?
In Hillsborough, there are several vacation homes available for rent that feature both pools and hot tubs. This affluent suburban area is known for its beautiful landscapes and tranquil environment, making it an ideal getaway. Travelers can expect amenities such as private swimming pools, relaxing hot tubs, spacious outdoor patios, and fully equipped kitchens, great for enjoying leisurely days and evenings.
Are there any Hillsborough vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Hillsborough with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay vacation rentals in Hillsborough?
A long-stay vacation rental in Hillsborough is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Hillsborough for a vacation rental?
March marks the beginning of the peak season in Hillsborough, making it an ideal time for travelers looking to enjoy the area's serene beauty and outdoor offerings. From March through May, the climate is pleasantly mild, with temperatures ranging from the low 40s to high 60s Fahrenheit, creating superb conditions for exploring the picturesque landscapes and charming neighborhoods on foot or by bike.

During this vibrant season, visitors can partake in a variety of activities, including leisurely strolls through the local parks or enjoying the blooming gardens that showcase the region's natural beauty. Hillsborough's proximity to the bustling attractions of the San Francisco Bay Area provides a convenient base for day trips, allowing guests to experience both tranquility and adventure.

For those considering a visit that is a bit lighter on the wallet, October is a wonderful month to explore Hillsborough. The fall season brings a unique charm, with cooler temperatures and fewer crowds, allowing for peaceful exploration of the area's scenic vistas and cultural attractions. Plus, the autumn foliage adds a stunning backdrop to your adventures.

Ultimately, whether you choose to visit during the lively peak months or the tranquil shoulder season, Hillsborough offers a wealth of experiences that cater to your preferences for quality and convenience.
How early should I book a Hillsborough vacation rental?
Book your Hillsborough vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Hillsborough?
In Hillsborough, California, visitors can enjoy a serene, upscale environment characterized by beautiful homes and lush landscapes. While the area is primarily residential, travelers can appreciate the stunning architecture of the local mansions and the well-maintained gardens that dot the neighborhood. Nearby, the San Mateo County History Museum in Redwood City offers insights into the region's past, just a short drive away. For outdoor enthusiasts, the nearby Crystal Springs Reservoir provides opportunities for hiking and picnicking with picturesque views.
Can I change or cancel my Hillsborough home rental booking on Vrbo?
To find Hillsborough vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Hillsborough vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.