A curving road lined with trees and grass.

San Mateo Vacations from $510

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your San Mateo Vacation

Our vacation packages to San Mateo let you customize your own adventure. Tailor your journey to suit your needs and interests and make the most of your time in this interesting city. A trip to San Mateo is a terrific opportunity to sightsee. Be sure to stop by big-name attractions such as Ravine Gardens State Park, Dunns Creek State Park and Palatka Municipal Golf Course. Whoever you're escaping with and whatever you plan to spend, your dream San Mateo vacation is only clicks away with Expedia.

The Latest San Mateo Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 20 - Jan 24

    The Villas of Amelia Island + Flight

    Fernandina Beach
    4 nights
    4.0 star property
    8.4/10 - Very good (1,288 reviews)
    "We had a wonderful stay at The Omni. They offer so much on the property. I highly recommend staying there. Definitely would go back!"
    Reviewed November 1, 2026
    Roundtrip • New York (EWR) - Jacksonville (JAX)
    EWR - JAX • Nonstop JAX - EWR • Nonstop
    $672
    $510
    per traveler
    found 1 day ago
    The Villas of Amelia Island
  • Dec 27 - Jan 1

    Hammock Beach Golf Resort & Spa + Flight

    Palm Coast
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,001 reviews)
    Roundtrip • New York (EWR) - Jacksonville (JAX)
    EWR - MCO • 1 stop MCO - EWR • 1 stop
    $1,789
    $1,350
    per traveler
    found 1 day ago
    Hammock Beach Golf Resort & Spa
  • Jan 17 - Jan 23

    Hoyt House Amelia Island + Flight

    Fernandina Beach Historic District
    6 nights
    3.5 star property
    9.6/10 - Exceptional (596 reviews)
    Roundtrip • Pittsburgh (PIT) - Jacksonville (JAX)
    PIT - JAX • Nonstop JAX - PIT • 1 stop
    Save 100% on your flight
    $1,386
    $1,066
    per traveler
    found 1 day ago
    Hoyt House Amelia Island
  • Jan 20 - Jan 24

    Seaside Amelia Inn + Flight

    Fernandina Beach
    4 nights
    3.0 star property
    8.8/10 - Excellent (1,160 reviews)
    "Everything from location, staff and room was exceptional!"
    Reviewed October 30, 2026
    Roundtrip • New York (EWR) - Jacksonville (JAX)
    EWR - JAX • Nonstop JAX - EWR • Nonstop
    $676
    $522
    per traveler
    found 1 day ago
    Seaside Amelia Inn
  • Dec 27 - Jan 1

    Landing Apartments Downtown Palm Coast + Flight

    Town Center
    5 nights
    4.0 star property
    9.8/10 - Exceptional (6 reviews)
    "I've stayed in a lot of hotels and this was the most luxurious. Clean, full kitchen, two bedrooms, walk-in closets, and three large flat screen TV and a balcony. I will be returning!!"
    Reviewed October 17, 2026
    Roundtrip • New York (EWR) - Jacksonville (JAX)
    EWR - MCO • 1 stop MCO - EWR • 1 stop
    $1,479
    $1,156
    per traveler
    found 1 day ago
    Landing Apartments Downtown Palm Coast

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 vacation package cost?

Offering great value package deals from $510 on Expedia, you'll be pleasantly surprised at how much a vacation to San Mateo costs! Our packages make travel planning easier and your savings go further.

What are the cheapest months to go to San Mateo?

You can typically find reduced prices and greater availability in January, June and July. Explore our cheap San Mateo vacation packages and you could get some great off-season discounts.

How many days is enough for San Mateo?

Typically, a handful of days is enough to see the major sights during your San Mateo vacation. But if you'd like to have more time to rest or take day tours, think about extending your itinerary.

How to find the best San Mateo package deals?

Begin your search for a San Mateo package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect San Mateo package deal right away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your San Mateo adventure off to a flying start.

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

An Expedia vacation package could land you considerable savings when compared to booking accommodations and flights separately. Better still, you can personalize your San Mateo escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.

When to book a vacation package to San Mateo?

If you're planning a spontaneous San Mateo getaway, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking ahead.

Does Expedia offer Book Now, Pay Later San Mateo vacation packages?

If you're anything like us, you love discovering new places but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your San Mateo trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.