Redwood Estates Vacations from $403

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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.

The Latest Redwood Estates vacation packages

Price found within the past 48 hours. Click for updated prices.
Aqua Breeze Inn

Aqua Breeze Inn

2.5 out of 5
Westside Santa Cruz
Save 100% on your flight
Price was $688, price is now $403 per person
$403
per person
Sep 22 - Sep 26
found 14 hours ago
Roundtrip flight included
Los Angeles (LAX) to San Jose (SJC)
8.2/10 Very Good! (1,007 reviews)
This was the perfect motel to stay at for our trip to Santa Cruz. It was clean, the beds were comfortable and it was so close to all the amenities, The staff was wonderful too.

Reviewed on Jul 1, 2026

Stanford Court San Francisco

Stanford Court San Francisco

4 out of 5
Downtown San Francisco
Save 100% on your flight
Price was $1,025, price is now $535 per person
$535
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip flight included
Carlsbad (CLD) to San Francisco (SFO)
9/10 Wonderful! (1,462 reviews)
We opted for a premier king room. The view was exceptional. The staff was so helpful, kind, and accommodating. We will definitely be back!

Reviewed on Jul 2, 2026

Hotel Riu Plaza Fisherman's Wharf

Hotel Riu Plaza Fisherman's Wharf

4 out of 5
Fisherman's Wharf
Save 100% on your flight
Price was $1,465, price is now $800 per person
$800
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip flight included
Carlsbad (CLD) to San Francisco (SFO)
9/10 Wonderful! (7,477 reviews)
Ideal location to stay to explore The City

Reviewed on Jul 3, 2026

The Jay, Autograph Collection

The Jay, Autograph Collection

4 out of 5
Downtown San Francisco
Save 100% on your flight
Price was $1,726, price is now $953 per person
$953
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip flight included
Carlsbad (CLD) to San Francisco (SFO)
9.4/10 Exceptional! (438 reviews)
the credit card machine was not working properly at checkin- instead of trying to resolve it the host was acting like it was my cards that were not working.

Reviewed on Jun 29, 2026

Beacon Grand, A Union Square Hotel

Beacon Grand, A Union Square Hotel

4 out of 5
Union Square
Save 100% on your flight
Price was $1,174, price is now $679 per person
$679
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip flight included
Carlsbad (CLD) to San Francisco (SFO)
9/10 Wonderful! (2,106 reviews)
Great place with cool bar at the top

Reviewed on Jun 30, 2026

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What to do in Redwood Estates

Private Walking Tour in Stanford University

Stanford University Personalized Self-Guided App Tour

$5
per traveler
Stanford University Personalized Self-Guided App Tour
Picture 2 for Activity San Jose: Valley Ghosts Haunted Walking Tour

San Jose Ghost Tour: The Scythe, Sacrifice, & Silhouette

$32
per adult
San Jose Ghost Tour: The Scythe, Sacrifice, & Silhouette
Self Guided Walking Tour in Agnews Historic Park

Agnews Historic Park Personalized Self-Guided App Tour

$5
per traveler
Agnews Historic Park Personalized Self-Guided App Tour
See all activities in Redwood Estates

Redwood Estates Hotel Deals

Wild Palms, a JdV by Hyatt Hotel

Wild Palms, a JdV by Hyatt Hotel

3 out of 5
910 E Fremont Ave Sunnyvale CA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $105 total per night from Jul 17 to Jul 18
$105 total
Jul 17 - Jul 18
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
"The continental breakfast is great! It’s a city eclectic boutique hotel, with a nice pool, spa, fitness center and small game room. The rooms are ok. A little outdated. No smart TVs. The staff were nice but some seemed maybe new or in training. Very family friendly. Great location. We would stay ..."

Reviewed on Jun 29, 2026

Wild Palms, a JdV by Hyatt Hotel
Sonesta Silicon Valley

Sonesta Silicon Valley

4 out of 5
1820 Barber Ln Milpitas CA
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $114 total per night from Jul 4 to Jul 5
$114 total
Jul 4 - Jul 5
Total with taxes and fees
9.2/10 Wonderful! (2,012 reviews)
"Great place to stay! Will definitely be booking again!"

Reviewed on Jul 3, 2026

Sonesta Silicon Valley
La Bahia Hotel and Spa

La Bahia Hotel and Spa

4.5 out of 5
215 Beach Street Santa Cruz CA
Fully refundableReserve now, pay when you stay
$419 nightly
The price is $470 total per night from Jul 5 to Jul 6
$470 total
Jul 5 - Jul 6
Total with taxes and fees
9.6/10 Exceptional! (365 reviews)
"Watch out some of the rooms are road facing and if you don't pay attention they might want you to take that up"

Reviewed on Jul 2, 2026

La Bahia Hotel and Spa
See all 2,531 properties in Redwood Estates
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

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Frequently asked questions

How much does a Redwood Estates vacation package cost?
Offering great value package deals from $403 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.

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