A coastal landscape with a sandy beach, rocky cliffs, and the ocean.

San Mateo Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in San Mateo

Find the best San Mateo areas for the activities you enjoy most. Learn more about San Mateo
Learn more about San Mateo

Downtown San Mateo

City centre San Mateo blends business energy with Japanese cultural influences. The commercial heart of the city buzzes with office buildings and banks by day. Along B Street and 3rd Avenue, diverse restaurants and entertainment venues create a lively atmosphere for visitors and locals alike. Explore the tranquil Japanese Garden with its koi ponds and traditional landscaping. Catch a film at Cinemark Century San Mateo 12 after shopping at unique boutiques. The neighborhood's walkable streets make it easy to discover authentic Japanese eateries and modern cafes.

North Central

North Central offers a peaceful retreat in San Mateo with tree-lined streets and charming homes. This residential haven provides authentic suburban living just minutes from major attractions. You'll find budget-friendly accommodation compared to nearby San Francisco. The convenient location gives easy access to the entire Bay Area. The area connects travellers to San Francisco and Silicon Valley via nearby Caltrain and highways. Take a short drive to enjoy Coyote Point Park or the Japanese Garden. While quiet at night, you'll appreciate the clean streets and welcoming community atmosphere.

Highlands-Baywood Park

Highlands-Baywood Park offers a peaceful retreat in San Mateo where tree-lined streets and well-kept homes create a quintessential American suburban scene. The area parks invite visitors to enjoy playgrounds, walking paths, and open green spaces away from city noise. Children's laughter and birdsong provide the soundtrack to this residential haven. The area's quiet charm makes it perfect for morning jogs or evening strolls under mature oak trees. While shopping and dining options are limited within the area, city centre San Mateo's attractions are just a short drive away. Crystal Springs Golf Course and Hillsdale Shopping Centre sit nearby for added convenience.

Sugarloaf

This peaceful San Mateo area offers a serene retreat with tree-lined streets and mountain views. Sugarloaf's well-maintained homes create an authentic suburban California experience away from tourist crowds. Hiking trails on nearby Sugarloaf Mountain provide outdoor recreation for nature lovers. Families appreciate the quiet residential setting and easy access to Hillsdale Shopping Centre just outside the area. While Sugarloaf itself has minimal dining or retail options, San Mateo's city centre is a short drive away. The lush landscaping and mountain vistas make this area perfect for travellers seeking a genuine suburban escape.

Hillsdale

Hillsdale blends suburban calm with convenient Bay Area connections. This family-friendly San Mateo area centers around its massive shopping centre and modern Caltrain station. Quiet residential streets with well-maintained homes provide a peaceful retreat from urban bustle. Outdoor enthusiasts can explore Bay Meadows Park and other local green spaces. The San Mateo County Event Centre hosts festivals and live music throughout the year. With easy access to Highway 101, you're just a short ride from San Francisco and Silicon Valley attractions.

Discover the most popular places to visit in San Mateo

San Mateo Hotel Deals

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently Asked Questions

How much does a San Mateo holiday package cost?

You'll find cheap prices on Expedia for your San Mateo escape. However, factors like the hotel choice, length of stay and season will determine how much your holiday to San Mateo costs.

What are the cheapest months to go to San Mateo?

You're likely to find lower prices and greater availability in December, January and February. Explore our cheap San Mateo holiday packages and you could get some great off-season deals.

How many days is enough for San Mateo?

We'd recommend booking a San Mateo holiday for at least 3 days. This gives you plenty of time to check off key attractions such as CuriOdyssey and Coyote Point Park, as well as check out neighbourhoods like East San Mateo and Shoreview. You could even slot in a day trip (or two) from San Mateo.

Is it worth booking a holiday package to San Mateo?

Whether you're planning to check out attractions like Coyote Point Park and Hillsdale Shopping Centre, or eager to experience its top-notch history and culture, a San Mateo holiday guarantees an unforgettable adventure. Book your trip with Expedia and discover why San Mateo is such a good holiday destination.

How to find the best San Mateo package deals?

Finding a cheap San Mateo package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, add a few filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most economical San Mateo package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.

Is it cheaper to book a San Mateo holiday as a package?

You can enjoy significant savings on your next San Mateo escape by booking a tailored holiday package. Click on the "Package" heading, then select your travel dates and destination to see some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.

When to book a holiday package to San Mateo?

If you're planning a spur-of-the-moment San Mateo getaway, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking well in advance.

How to plan a trip to San Mateo?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit San Mateo.
  2. Set your budget: Consider expenses like flights, meals and transportation when calculating how much to set aside for your trip to San Mateo. Then, select a hotel that suits your budget, whether that's an affordable stay or a high-end getaway.
  3. Work out your trip length: Consider how much time you want to spend exploring San Mateo. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick a San Mateo holiday package that brings all your bookings together.