Title: Woodside Vacation Packages 2026 from $427 | Expedia.com

[Woodside Travel Guide](https://expedia.com/Redwood-City-Woodside.dx179364)[Hotels in Woodside](https://expedia.com/Woodside-Redwood-City-Hotels.0-n179364-0.Travel-Guide-Filter-Hotels)[Flights to Redwood City](https://expedia.com/Cheap-Flights-To-Redwood-City.d9465.Travel-Guide-Flights)[Things to do in Redwood City](https://expedia.com/Things-To-Do-In-Redwood-City.d9465.Travel-Guide-Activities)[Car Rentals in Woodside](https://expedia.com/Car-Rentals-In-Woodside.d179364.Car-Rental-Guide)

![](https://images.trvl-media.com/place/179364/1f571892-47c5-44aa-9987-5a18a8d35130.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Woodside Vacations from $427

## Book a Hotel + Flight or Car together to unlock savings

## 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](https://www.expedia.com/Huddart-Park-Redwood-City.d6183209.Vacation-Attraction) and [Edgewood Park & Natural Preserve](https://www.expedia.com/Edgewood-Park-Natural-Preserve-Farm-Hills.d553248635997928026.Vacation-Attraction). 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.

![Hotel Riu Plaza Fisherman's Wharf](https://images.trvl-media.com/lodging/1000000/30000/24700/24625/75f20517_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Fisherman's Wharf

Fisherman's Wharf

Save 100% on your flight

$427

per person

May 7 - May 10

found 1 day ago

Roundtrip flight included

Carlsbad (CLD) to San Francisco (SFO)

9/10 Wonderful! (7,413 reviews)

Great place, clean, amazing breakfast. Will come back for sure

Reviewed on Mar 19, 2026

![1 Hotel San Francisco](https://images.trvl-media.com/lodging/2000000/1140000/1138300/1138217/60488ea7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 1 Hotel San Francisco

Downtown San Francisco

Save 100% on your flight

$1,097

per person

Apr 23 - Apr 27

found 7 hours ago

Roundtrip flight included

Dallas (DFW) to San Francisco (SFO)

9.2/10 Wonderful! (516 reviews)

Great staff & very clean facility

Reviewed on Mar 14, 2026

![Appellation Healdsburg](https://images.trvl-media.com/lodging/119000000/118740000/118739000/118738917/e8f2b209_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Appellation Healdsburg

Save 100% on your flight

$1,403

per person

Jun 4 - Jun 9

just found

Roundtrip flight included

New York (JFK) to San Francisco (SFO)

9/10 Wonderful! (53 reviews)

Everything was clean, comfortable, and stylish.

Reviewed on Mar 11, 2026

![Sonoma Sunshine by Avantstay Countryside Views](https://images.trvl-media.com/lodging/100000000/99670000/99666300/99666249/7d04b552_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sonoma Sunshine by Avantstay Countryside Views

Save 100% on your flight

$4,088

per person

Jun 4 - Jun 9

just found

Roundtrip flight included

New York (JFK) to San Francisco (SFO)

No reviews

![Montage Healdsburg](https://images.trvl-media.com/lodging/58000000/57180000/57174000/57173926/09c9e897_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Montage Healdsburg

Save 100% on your flight

$4,130

per person

Jun 4 - Jun 9

just found

Roundtrip flight included

New York (JFK) to San Francisco (SFO)

9.6/10 Exceptional! (131 reviews)

This hotel was amazing. Like a cabin in the woods. Beautiful property, room, and location. Exceptional service.

Reviewed on Mar 4, 2026

## Woodside Hotel Deals

![Bay Landing San Francisco Airport Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1110800/1110785/b6378346_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Bay Landing San Francisco Airport Hotel

1550 Bayshore Hwy Burlingame CA

Fully refundableReserve now, pay when you stay

$179 nightly

$202 total

Apr 2 - Apr 3

Total with taxes and fees

9/10 Wonderful! (4,826 reviews)

Friendly staff, very clean and quiet.

Reviewed on Mar 19, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F2%2F2026&endDate=4%2F3%2F2026&selected=1110785&PinnedHotelID=1110785&HadPinnedHotel=true&regionId=179364)

![Best Western Plus Grosvenor Airport Hotel](https://images.trvl-media.com/lodging/1000000/10000/7700/7635/bfe2c1f2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Best Western Plus Grosvenor Airport Hotel

380 S Airport Boulevard South San Francisco CA

Fully refundableReserve now, pay when you stay

$107 nightly

$126 total

Apr 3 - Apr 4

Total with taxes and fees

8.4/10 Very Good! (1,733 reviews)

Near airport but property not clean. They also charge for parking.

Reviewed on Mar 19, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F3%2F2026&endDate=4%2F4%2F2026&selected=7635&PinnedHotelID=7635&HadPinnedHotel=true&regionId=179364)

![Travelodge by Wyndham San Francisco Airport North](https://images.trvl-media.com/lodging/1000000/20000/17000/16955/864c4988_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Travelodge by Wyndham San Francisco Airport North

326 S Airport Blvd South San Francisco CA

Fully refundableReserve now, pay when you stay

$60 nightly

$72 total

Mar 29 - Mar 30

Total with taxes and fees

6/10 (3,335 reviews)

Dirty room with a lot of mold

Reviewed on Mar 19, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=16955&PinnedHotelID=16955&HadPinnedHotel=true&regionId=179364)

[See all 3,261 properties in Woodside](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F21%2F2026&endDate=3%2F22%2F2026&regionId=179364)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Kid Friendly Vacations

[](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

LGBTQ Friendly Vacations

[](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adventure Vacations

[](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click)

![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Where to go when

[](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Honeymoon Vacations

[](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Mountain Vacations

[](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Fishing Vacations

[](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adults Only Vacations

[](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Waterpark Vacations

[](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Scuba Diving Vacations

[](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Yoga Vacations

[](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Cheap Vacations

[](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Solo Vacations

[](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click)

### Discover the most popular places to visit in Woodside

![Beautiful view of the garden with white tulips and the clock tower, Filoli Garden](https://images.trvl-media.com/place/502568/e228ec95-7b01-4053-8995-a62ef151ea21.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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. 

[](https://expedia.com/Filoli-Redwood-City.d502568.Vacation-Attraction)

![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.](https://images.trvl-media.com/place/9465/42ffefdd-d084-4060-b9f3-d0512baf388d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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. 

[](https://expedia.com/Fox-Theatre-Downtown-Redwood-City.d553248635359189571.Vacation-Attraction)

![Aerial view of the Miller Sweeney Bridge And Fruitvale Railroad Bridge , showing the intricate metalwork and surrounding cityscape., Alameda, California, USA](https://images.trvl-media.com/place/553248621532640401/92420f52-abca-42db-8b2d-9226e23a0036.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### The Foundry

Catch an event at The Foundry, and enjoy other activities in Redwood City such as hiking. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area. 

[](https://expedia.com/The-Foundry-Friendly-Acres.d553248621532640401.Vacation-Attraction)

### Things to do

![Private Walking Tour in Stanford University ](https://mediaim.expedia.com/localexpert/46749478/62859780-e196-4c1f-8ba7-a221f671a6bf.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Stanford University Personalized Self-Guided App Tour

$5

per traveler

[](https://expedia.com/things-to-do/stanford-university-personalized-self-guided-app-tour.a46749478.activity-details)

![Two Flight Indoor Skydiving Experience ](https://mediaim.expedia.com/localexpert/2573266/645e65ca-17f1-4b08-85bc-c2bd84f2f5f2.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Two Flight Indoor Skydiving Experience

$125

per traveler

**80%** of travellers recommend

[](https://expedia.com/things-to-do/two-flight-indoor-skydiving-experience.a2573266.activity-details)

![Silicon Valley Tech Tour](https://mediaim.expedia.com/localexpert/475414/6027414a-4e5f-4c87-9d71-79d7d86452e5.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Silicon Valley Tech Tour

$185

per adult

[](https://expedia.com/things-to-do/silicon-valley-tech-tour.a475414.activity-details)

[See all activities in Redwood City](https://expedia.com/things-to-do/search?rid=179364)

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