Woodside Vacations from $418

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Your Woodside Vacation

Known for its nature and hiking, Woodside draws visitors from all corners of the globe. Let our Woodside vacation packages give you a glimpse into this neighborhood and everything it has to offer. Get your trip to Woodside off to a great start by exploring some of its nearby attractions, such as Huddart Park and Edgewood Park & Natural Preserve. Expedia is here to help put your plans into action. Book your ideal Woodside vacation now.

The Latest Woodside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Stevenson Monterey

The Stevenson Monterey

2.5 out of 5
Downtown Monterey
Save 100% on your flight
Price was $705, price is now $418 per person
$418
per person
Feb 4 - Feb 11
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Francisco (SFO)
8.8/10 Excellent! (1,004 reviews)
Friendly staff, clean room, parking on site, great location.

Reviewed on Dec 2, 2025

The Phoenix Hotel

The Phoenix Hotel

3 out of 5
Downtown San Francisco
Price was $1,125, price is now $567 per person
$567
per person
Jan 6 - Jan 13
found 1 day ago
Roundtrip flight included
Burbank (BUR) to San Francisco (SFO)
9/10 Wonderful! (1,004 reviews)
Excellent customer service, aesthetic fantastic, beautiful details, one of a kind. You have to stay here at least once! Culturally iconic.

Reviewed on Nov 30, 2025

Montage Healdsburg

Montage Healdsburg

5 out of 5
Price was $2,060, price is now $1,086 per person
$1,086
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Burbank (BUR) to San Francisco (SFO)
9.6/10 Exceptional! (113 reviews)
Clean room, kind and helpful staff. Nice ambiance in vineyard.

Reviewed on Nov 30, 2025

Hotel Julian

Hotel Julian

3 out of 5
Downtown San Francisco
Save 100% on your flight
Price was $1,492, price is now $913 per person
$913
per person
Jan 12 - Jan 14
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Francisco (SFO)
8.6/10 Excellent! (559 reviews)
Staff were great, the rooms ac wasn’t really cooling b

Reviewed on Nov 25, 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 $1,710, price is now $1,066 per person
$1,066
per person
Jan 19 - Jan 26
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to San Jose (SJC)
No reviews

Black Friday Sale

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Woodside Hotel Deals

Best Western Plus Grosvenor Airport Hotel

Best Western Plus Grosvenor Airport Hotel

3 out of 5
380 S Airport Boulevard South San Francisco CA
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $108 total per night from Dec 19 to Dec 20
$108 total
Dec 19 - Dec 20
Total with taxes and fees
8.4/10 Very Good! (1,688 reviews)
Everything was great

Reviewed on Nov 27, 2025

Best Western Plus Grosvenor Airport Hotel
Bay Landing San Francisco Airport Hotel

Bay Landing San Francisco Airport Hotel

3 out of 5
1550 Bayshore Hwy Burlingame CA
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $170 total per night from Jan 2 to Jan 3
$170 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
9/10 Wonderful! (4,741 reviews)
The room was cleanly and spacious. I had a small refrigerator and a microwave. The staff was very friendly and helpful.

Reviewed on Nov 30, 2025

Bay Landing San Francisco Airport Hotel
Crowne Plaza San Francisco Airport by IHG

Crowne Plaza San Francisco Airport by IHG

3.5 out of 5
1177 Airport Blvd Burlingame CA
Fully refundable
$87 nightly
The price is $99 total per night from Dec 18 to Dec 19
$99 total
Dec 18 - Dec 19
Total with taxes and fees
7.6/10 Good! (2,504 reviews)
Great

Reviewed on Nov 30, 2025

Crowne Plaza San Francisco Airport by IHG
See all 3,175 properties in Woodside
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Kid Friendly Vacations

Discover the most popular places to visit in Woodside

The historic Fox Theatre in Redwood City that opened in 1929 and was remodeled in 1950. The Moorish feel and style on the inside and the Gothic feel on the outside clearly tells why this iconic place was inducted to the National Register of Historic Places.

Fox Theatre

You can enjoy a show at Fox Theatre during your trip to Redwood City. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Fox Theatre
You can fin the oldest trees in this park

Marlin Park

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

Marlin Park

Filoli

Find out about the history of Redwood City when you spend time at Filoli. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Filoli

Things to do

Two Flight Indoor Skydiving Experience

Two Flight Indoor Skydiving Experience

$120
per traveler
Two Flight Indoor Skydiving Experience
Silicon Valley Tech Tour

Silicon Valley Tech Tour

$185
per adult
Silicon Valley Tech Tour
Rock Climbing 2 - Beyond the Basics

Outdoor Rock Climbing - Level 2

$119
per adult
Outdoor Rock Climbing - Level 2
See all activities in Redwood City
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.