Redwood Estates Vacations from $343

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 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 Redwood Estates Vacation

When a break in the city is calling, answer it with a vacation package to Redwood Estates. The neighborhood of South San Jose, which is great for culture, golfing and mountain biking, makes a wonderful base for your adventures. If your trip to Redwood Estates includes some sightseeing, hit up famous attractions like Testarossa Winery, Old Town Los Gatos and Vasona Lake County Park. Don't put off exploring this destination any longer. The ultimate Redwood Estates vacation is a couple of clicks away with Expedia.

The Latest Redwood Estates vacation packages

Price found within the past 48 hours. Click for updated prices.
Fitzgerald Hotel
Bay Landing San Francisco Airport Hotel
Hotel Riu Plaza Fisherman's Wharf
The Phoenix Hotel
Parc 55 San Francisco - A Hilton Hotel
Don't see what you're looking for?
See all available trips from Columbus to Redwood Estates
View all trips

Discover the most popular places to visit in Redwood Estates

What to do in Redwood Estates

Redwood Estates Hotel Deals

The Domain Hotel

The Domain Hotel

4 out of 5
1085 E El Camino Real, Sunnyvale, CA
$109 nightly
The price is $123 total per night from Dec 5 to Dec 6
$123 total
Dec 5 - Dec 6
Total with taxes and fees
8/10 Very Good! (1,326 reviews)
Staff was superb in taking care of needs but I feel the hotel staff could work on cleanliness a bit more Microwave and breakfast tables need to be cleaned after each use by staff - there was a puddle of oily water before I used the microwave; breakfast tables should be cleaned after each use I understand ...

Reviewed on Nov 10, 2025

The Domain Hotel
Maple Tree Inn

Maple Tree Inn

3 out of 5
711 E El Camino Real Sunnyvale CA
9/10 Wonderful! (2,382 reviews)
amazing!

Reviewed on Nov 11, 2025

Maple Tree Inn
Sonesta Select San Jose Airport

Sonesta Select San Jose Airport

3 out of 5
1727 Technology Dr San Jose CA
8.6/10 Excellent! (1,583 reviews)
Should have more option for all meals of the day.

Reviewed on Nov 13, 2025

Sonesta Select San Jose Airport
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.

Find the Best Redwood Estates Vacation Packages

Redwood Estates Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Norman Y. Mineta San Jose Intl. Airport (SJC)
Top Sights
Testarossa Winery, Regale Winery and Vineyards and Loma Prieta Winery

More vacations you might like

Frequently asked questions

How much does a Redwood Estates vacation package cost?
Offering great value package deals from $343 on Expedia, you'll be thrilled with how little a vacation to Redwood Estates costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Redwood Estates?
January, October and December are great times to look for cheap Redwood Estates vacation packages. Traveling in less busy periods means you can usually find reduced prices on flights and accommodations.
How many days is enough for Redwood Estates?
With a well-organized itinerary, you can easily hit the top Redwood Estates sights in a few days. But if you prefer to discover hidden gems or go on day tours, consider booking your Redwood Estates vacation for longer.
How to find the best Redwood Estates package deals?
Use Expedia's filter tool to help you find some fabulous Redwood Estates package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Redwood Estates package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Redwood Estates vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations separately. Better still, you can personalize your Redwood Estates trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Redwood Estates?
If you have your Redwood Estates vacation dates locked in, book early to grab some outstanding deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Redwood Estates vacation packages?
Your Redwood Estates getaway should be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

Explore a world of travel with Expedia

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