Choose from 29 vacation rentals located in Woodside, California. Top filters in Woodside include Internet / Wifi, Kitchen / Kitchenette, and Parking. Prices range from $72 to $2,770 per night. Our most popular vacation rental types near Woodside are Condo and Hotel.

Top vacation rentals in Woodside

Property grounds
4.8
Outstanding(29 Reviews)
House
 in Redwood City
3 bed 2 bath home in heart of Silicon Valley
8 guests · 3 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Air conditioner

This inviting House in Woodside can fit your needs for many types of vacations, at $313 per night.

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Property view
5.0
Outstanding(10 Reviews)
Bed and Breakfast
 in Woodside
Stonewood Private Luxury Guest House
4 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

Looking to create some memories in Woodside? Look no further than our Bed and Breakfast, Stonewood Private Luxury Guest House. Enjoy top-rated amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Property view
4.0
Good(No Reviews)
Vacation rental
 in Woodside
Exquisite Estately Villa
Garden · Pool · Kitchen / Kitchenette

Vacation rental in Woodside, for $93 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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Property view
3.5
Average(1 Review)
House
 in Palo Alto
Log-Cabin Home Retreat - Walk to Restaurants Trails Hiking & Biking
Pets allowed · Kitchen / Kitchenette · Internet / Wifi

Soak up the beauty of Woodside in our House, Log-Cabin Home Retreat - Walk to Restaurants Trails Hiking & Biking. With a range of amenities such as Fireplace, Internet / Wifi and Laundry, you'll feel right at home.

$$$$
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Search by amenity

Vacation rentals with internet & wifi in Woodside

Living room
4.5
Excellent(4 Reviews)
Bed and Breakfast
 in Woodside
Lovely, peaceful and close to everything!
6 guests · 2 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Internet / Wifi

This Bed and Breakfast for $450 in Woodside, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Enjoy the spa with breathtaking sunset views!
5.0
Outstanding(6 Reviews)
Villa
 in Woodside
Exquisite Estately Villa
6 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

Nestled in Woodside, this Villa is perfect for your next vacation. Enjoy Exquisite Estately Villa's top-rated amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Private kitchen
4.8
Outstanding(7 Reviews)
House
 in Woodside
Exquisite luxury executive 2-suite cottage
6 guests · 2 bedrooms · 3 baths
Garden · Pool · Kitchen / Kitchenette

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Woodside, at $913 per night for your next great vacation.

$$$$
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Living area
5.0
Outstanding(3 Reviews)
Condo
 in Woodside
Estately Plausibility of Simplicity
4 guests · 1 bedroom · 1 bath
Garden · Pool · Kitchen / Kitchenette

This Condo in Woodside, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Woodside

Woodside travel guide

Let us help you plan your perfect Woodside vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Woodside, and more.

Frequently asked questions

What is the price range for rentals in Woodside?

Vacation rentals in Woodside have a price range between $72-$2,770. The average price for rentals in Woodside is $325 per night.

What are the top things to do in Woodside, CA?

Woodside, CA is home to many exciting attractions and activities. From hiking and biking to exploring the local history and culture, there is something for everyone to enjoy. Here are the top things to do in Woodside, CA:

  • Hiking and biking through the hills and trails
  • Exploring the Woodside Store and Museum
  • Visiting the Filoli Historic House and Garden
  • Tasting wine at the Woodside Vineyards and Winery

What are the most popular vacation rental amenities in Woodside, CA?

The most popular vacation rental amenities in Woodside, CA include:

  • WiFi
  • Air conditioning
  • Parking
  • Hot tub
  • Swimming pool

WiFi is the top amenity, as it allows travelers to stay connected during their stay. Air conditioning is also popular, especially during the warm summer months. Many vacation rentals also offer parking, so guests can easily get around without needing to rent a car. Hot tubs are a great way to relax and unwind after a long day of sightseeing. Lastly, swimming pools are a great way to cool off during the hot summer days.

Where is Woodside, CA?

Woodside, CA is a small town located in San Mateo County, California. It is situated between Redwood City and San Francisco, and is known for its rural atmosphere, horse trails, and expansive estates. It is located about 20 miles south of San Francisco in the mid-Peninsula region of the San Francisco Bay Area.

What are the best neighborhoods to visit in Woodside, CA?

The best neighborhoods to visit in Woodside, CA are:

  • Emerald Hills
  • Woodside Glens
  • Woodside Highlands

Emerald Hills offers a great view of the San Francisco Bay, Woodside Glens is a great place to explore nature, and Woodside Highlands is the perfect place to enjoy the local culture.

What are the popular shopping destinations in Woodside, CA?

Woodside, CA is home to some of the best shopping destinations. Here are some of the most popular:

  • Woodside Village Shopping Center
  • Woodside Plaza
  • Woodside Shopping Center

Is Woodside, CA safe to travel to?

Woodside, CA is a safe place to travel to. Here are a few safety tips to keep in mind while visiting:
  • Be aware of your surroundings
  • Stay in well-lit and populated areas
  • Keep your valuables secure

What is the culture like in Woodside, CA?

Woodside, CA is a small community located in the San Francisco Bay Area. It's known for its strong sense of community, its natural beauty, and its commitment to preserving its rural atmosphere. Here are five points that describe the culture in Woodside:

  • Small-town atmosphere: Woodside is a tight-knit community with a strong sense of community and pride.
  • Outdoor activities: Woodside is home to many parks and trails, making it ideal for outdoor activities such as hiking, biking, and horseback riding.
  • Local events: Woodside hosts a number of annual festivals and events that bring the community together.
  • Commitment to preservation: Woodside is committed to preserving its rural atmosphere and is home to a number of local farms and ranches.
  • Cultural diversity: Woodside is home to a diverse population of people from all over the world.

Where can I find affordable accommodation in Woodside, CA?

Woodside, CA offers a variety of affordable accommodation options. Here are four of the best:

  • The Woodside Inn - a cozy and affordable inn located in the heart of the city.
  • The Woodside Hotel - a budget-friendly hotel with modern amenities.
  • The Woodside Apartments - a comfortable and affordable apartment complex located near downtown.
  • The Woodside Hostel - a great place to stay for those on a tight budget.

No matter your budget or accommodation needs, Woodside, CA has something for everyone.

How can I get around in Woodside, CA?

You can get around in Woodside, CA by:

  • Taking public transportation (Caltrain, SamTrans, and BART)
  • Walking or cycling
  • Renting a car or using ride sharing services (Uber, Lyft, etc.)

What are the must-visit tourist attractions in Woodside, CA?

Woodside, CA is a great place to visit, with plenty of attractions to explore. Here are some of the must-visit tourist attractions in Woodside:

  • Filoli Estate
  • Huddart Park
  • Alice's Restaurant
  • Woodside Store

The Filoli Estate is a stunning 654-acre estate with beautiful gardens and a historic mansion. Huddart Park is a great place for a picnic or a hike, and Alice's Restaurant is a popular spot for breakfast and lunch. Finally, the Woodside Store is a great place to grab a snack or souvenir.

What do I need to know before visiting Woodside, CA?

Before visiting Woodside, CA, it is important to know that the town is located in San Mateo County, and is known for its rural beauty and high-end residential real estate. Here are some other details to consider before visiting:

  • Woodside is home to several parks, including Wunderlich Park and Huddart Park.
  • The town is known for its equestrian community, and offers a variety of horseback riding opportunities.
  • Woodside is a popular destination for tech entrepreneurs and business leaders.

What are the most popular vacation rental amenities in Woodside?

  • Internet / Wifi
  • Kitchen / Kitchenette
  • Parking

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