Redwood Estates Vacation Packages
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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.
Top Redwood Estates Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Bartlett Hotel and Guesthouse
Union Square
CA $505
per person
Oct 7 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
8/10 Very good! (1,007 reviews)
First time getting a hotel so I was a bit nervous but they were able to help me with all my questions and made my stay so much
Reviewed on Sep 1, 2026
Treehouse Hotel Silicon Valley
CA $2,812
per person
Oct 4 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Francisco (SFO)
9.8/10 Exceptional! (148 reviews)
Spent my partners birthday weekend here. Loved the outdoor feel indoors. I upgraded our room to a 1 bedroom cabin. My 6yr old said it’s her favorite hotel so far, and she’s experienced some fancy hotels when we travel. The pool is spacious and every little detail in our room to the restaurant, I felt like so much thought was put into everything. We will be returning for a staycation soon. I highly recommend.
Reviewed on Sep 2, 2026
Stanford Court San Francisco
Downtown San Francisco
CA $625
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Francisco (SFO)
9/10 Wonderful! (1,608 reviews)
Location of this hotel was great with regards to Cable Car access as you have tracks on both California and Powell streets going both directions making easy access to Fisherman's Wharf, China Town, Little Italy and many other hot spots. Hotel staff were very helpful with recommendations on where to eat, have drinks, etc. That said, the hotel bar was a nice active place to finish the evenings out in so we could plan the next day. Met lots of interesting people from around the globe there.
Reviewed on Sep 2, 2026
Ready to book your vacation to Redwood Estates?
Redwood Estates Hotel Deals
Wild Palms, a JdV by Hyatt Hotel
910 E Fremont Ave Sunnyvale CA
Fully refundableReserve now, pay when you stay
CA $141
CA $158 total
Sep 11 - Sep 12
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"Clean facilities, helpful and friendly staff and wonderful amenities!"
Reviewed on Sep 2, 2026
Sonesta Silicon Valley
1820 Barber Ln Milpitas CA
Fully refundableReserve now, pay when you stay
CA $146
CA $167 total
Sep 12 - Sep 13
includes taxes & fees
La Bahia Hotel and Spa
215 Beach Street Santa Cruz CA
CA $406
CA $533 total
Sep 27 - Sep 28
includes taxes & fees
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.
What to do in Redwood Estates
Beach Hill to Historic Downtown Santa Cruz Loop
CA $62
per adult
Stanford University Personalized Self-Guided App Tour
CA $7
per traveller
Santa Cruz Walking Tour: Discover Downtown & Mission Hill
CA $62
per adult
Frequently asked questions
How much does a Redwood Estates vacation package cost?
You can pick up a vacation package to this popular destination from CA $505 on Expedia. But how much your vacation to Redwood Estates costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Redwood Estates?
You can generally find reduced prices and greater availability in January, February and April. Browse our cheap Redwood Estates vacation packages and you could land some great off-season deals.
How many days is enough for Redwood Estates?
Redwood Estates vacations can be as short or long as you like, but to get a real feel for this destination, we reckon 4 days is about right. In this timeframe, you can fit in headline attractions like Regale Winery and Vineyards and Villa del Monte Winery along with lesser-known spots. Don't skip cool areas such as Lexington Hills and Holy City either. If you plan wisely, you can even take a day trip or two from Redwood Estates too.
How to find the best Redwood Estates package deals?
Bagging a cheap Redwood Estates package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Redwood Estates package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Redwood Estates vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Redwood Estates vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Redwood Estates?
If you're planning a spontaneous Redwood Estates trip, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Redwood Estates?
- Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Redwood Estates.
- Set your budget: Consider costs such as flights, transportation and food when calculating how much to set aside for your trip to Redwood Estates. Then, select a hotel that suits your budget, whether that's a wallet-friendly option or a more upscale retreat.
- Decide how long to go for: Now that you're more familiar with Redwood Estates, you can work out the perfect length of your vacation. Create a draft itinerary and allocate enough time to cover everything you want to see.
- Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a personalized Redwood Estates vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
