East San Mateo Vacations from $375

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Your East San Mateo Vacation

Book an East San Mateo vacation package and discover the rhythm and way of life of this interesting neighborhood. With all your travel plans worked out, the only thing you need to worry about here is having a great time. Your trip to East San Mateo wouldn't be complete without exploring top attractions nearby such as Coyote Point Park, Hillsdale Shopping Center and Poplar Creek Golf Course. Stop dreaming and start doing. When it's time to lock in your ideal vacation to East San Mateo, Expedia will help get you there.

The Latest East San Mateo Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Fitzgerald Hotel

Fitzgerald Hotel

3 out of 5
Union Square
Save 100% on your flight
Price was $656, price is now $375 per person
$375
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip flight included
Burbank (BUR) to San Francisco (SFO)
15.6/10 Exceptional! (485 reviews)
I enjoyed my stay at The Fitzgerald. Its located at a very convenient area in Union Square and there are a wide variety of restaurants near by. Im aware this is an old building; however, the staff does a great job in cleaning, you can chose to have housekeeping every day. Had a mini fridge and a full bathroom (with tub), which was very convenient. There's also free continental breakfast from.7am to 10am.

Reviewed on Nov 24, 2025

San Carlos Inn

San Carlos Inn

2 out of 5
Price was $852, price is now $439 per person
$439
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to San Francisco (SFO)
14/10 Exceptional! (316 reviews)
room could have been cleaner fridge and micro wave were not spotless

Reviewed on Nov 21, 2025

Montage Healdsburg

Montage Healdsburg

5 out of 5
Price was $2,099, price is now $1,109 per person
$1,109
per person
Feb 12 - Feb 15
found 18 hours ago
Roundtrip flight included
Burbank (BUR) to San Francisco (SFO)
19.2/10 Exceptional! (113 reviews)
Overall, the property was beautiful. However, we had an issue with black beetles in our restroom. I notified the front desk after killing three of them myself and all they did was spray a menthol cleaning agent around the tub. In the morning, I woke up to five or six of them under the bathmat. This ruined room as I am deadly terrified of bugs. At checkout, I did let them know about this and they comped my parking which I feel was an understatement considering what an inconvenience it was to smash black bugs all night. Sad to say that I was not very comfortable.

Reviewed on Nov 2, 2025

Hotel Healdsburg

Hotel Healdsburg

4 out of 5
Save 100% on your flight
Price was $1,471, price is now $844 per person
$844
per person
Dec 26 - Dec 30
found 8 hours ago
Roundtrip flight included
Los Angeles (LAX) to San Francisco (SFO)
18.4/10 Exceptional! (427 reviews)
Nice Hotel close to everything. Valet took care of us everyday. Bartender could use a little help in customer service, was a little rude on a couple occasions. All in all great stay and a nice hotel

Reviewed on Nov 23, 2025

@ Marbella Lane - 3BR Designer Near Valley Fair

@ Marbella Lane - 3BR Designer Near Valley Fair

3 out of 5
Save 100% on your flight
Price was $2,974, price is now $1,713 per person
$1,713
per person
Feb 4 - Feb 7
found 2 hours ago
Roundtrip flight included
Carlsbad (CLD) to San Jose (SJC)
No reviews

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Where to stay in East San Mateo

Find the best East San Mateo areas and neighborhoods for the activities you enjoy most. Learn more about East San Mateo
Union Square which includes a high rise building and a city

Union Square

4/5(5,164 area reviews)

Major tourist destination in downtown San Francisco, Union Square boasts shopping, hotels, and theaters. Explore department stores, boutiques, and galleries, or catch a performance at various theaters. Enjoy the Dewey Monument and stunning views from nearby hotels. Easily accessible via cable car lines, buses, and subway systems.

Find hotels in Union Square

East San Mateo Hotel Deals

Holiday Inn Hotel & Suites San Mateo-San Francisco SFO by IHG

Holiday Inn Hotel & Suites San Mateo-San Francisco SFO by IHG

3 out of 5
330 N Bayshore Blvd San Mateo CA
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $84 total per night from Dec 11 to Dec 12
$84 total
Dec 11 - Dec 12
Total with taxes and fees
7.8/10 Good! (1,009 reviews)
the room was so spacuous and clean. the beds werr really comfy and the hotel staff was very friendly. would defi stay here again

Reviewed on Nov 23, 2025

Holiday Inn Hotel & Suites San Mateo-San Francisco SFO by IHG
Hilton San Francisco Financial District

Hilton San Francisco Financial District

4 out of 5
750 Kearny St San Francisco CA
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $119 total per night from Dec 14 to Dec 15
$119 total
Dec 14 - Dec 15
Total with taxes and fees
8.6/10 Excellent! (2,019 reviews)
Best ever thank you

Reviewed on Nov 17, 2025

Hilton San Francisco Financial District
Holiday Inn Golden Gateway by IHG

Holiday Inn Golden Gateway by IHG

3.5 out of 5
1500 Van Ness Ave San Francisco CA
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $132 total per night from Nov 30 to Dec 1
$132 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (4,867 reviews)
There wasnt much in the direct vicinity of the hotel but great location for public transport and the hotel has wonderful views and modern clean rooms. I wish the lobby was upgraded but the staff was grear!

Reviewed on Nov 24, 2025

Holiday Inn Golden Gateway by IHG
See all 5,039 properties in East San Mateo
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.
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Discover the most popular places to visit in East San Mateo

Los Prados Park

Los Prados Park is just one of the places to see in San Mateo, so why not enjoy the other things to explore during your travels? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Los Prados Park

Shoreview Park

After visiting Shoreview Park, make a plan to see the other sights and activities in San Mateo. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Shoreview Park

Parkside Aquatic Park

Parkside Aquatic Park is just one of the places to see in San Mateo, so why not enjoy the other things to explore during your travels? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Parkside Aquatic Park

Things to do

The Golden Hour

2hr. SUNSET Sailing Experience on San Francisco Bay

$149
per adult
2hr. SUNSET Sailing Experience on San Francisco Bay
Napa, Sonoma and Exclusive Battery Spencer Small Group Wine Tasting Tour

Napa, Sonoma and Exclusive Battery Spencer Small Group Wine Tasting Tour

$138
per traveler
Napa, Sonoma and Exclusive Battery Spencer Small Group Wine Tasting Tour
Stanford University Campus Adventure

Stanford University Campus Adventure

$10
per adult
Stanford University Campus Adventure
See all activities in San Francisco
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.