Redwood Estates Vacations from $656

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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.
Uptown Oasis San Jose Airport

Uptown Oasis San Jose Airport

3 out of 5
Rosemary
Price was $1,078, price is now $656 per person
$656
per person
Jul 23 - Jul 27
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to San Jose (SJC)
8/10 Very Good! (701 reviews)
Staff was nice. Pool and hot tub dirty. Asked for towels at 930 am and didn’t get them until the afternoon.

Reviewed on May 19, 2026

La Bahia Hotel and Spa

La Bahia Hotel and Spa

4.5 out of 5
Westside Santa Cruz
Save 100% on your flight
Price was $1,502, price is now $935 per person
$935
per person
Jul 2 - Jul 5
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to San Jose (SJC)
9.6/10 Exceptional! (266 reviews)
The room had beautiful furnishings and it was very clean. The bed was extremely comfortable. The pool area and bar staff were excellent. All staff were friendly and helpful. I would definitely stay again.

Reviewed on May 11, 2026

Marbella Lane - 3BR Designer Home 12-min to Levi's

Marbella Lane - 3BR Designer Home 12-min to Levi's

3 out of 5
Save 100% on your flight
Price was $5,141, price is now $3,275 per person
$3,275
per person
Jul 23 - Jul 27
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to San Jose (SJC)
No reviews
The Stevenson Monterey

The Stevenson Monterey

2.5 out of 5
Downtown Monterey
Save 100% on your flight
Price was $1,375, price is now $921 per person
$921
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to San Francisco (SFO)
8.8/10 Excellent! (1,017 reviews)
Good location and great for the late night arrival I needed.

Reviewed on May 18, 2026

1 Hotel San Francisco

1 Hotel San Francisco

5 out of 5
Downtown San Francisco
Save 100% on your flight
Price was $1,343, price is now $902 per person
$902
per person
Jul 24 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to San Francisco (SFO)
9.2/10 Wonderful! (540 reviews)
Amazing ambiance. Great staff and Daily Breakfast.

Reviewed on Apr 10, 2026

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Discover the most popular places to visit in Redwood Estates

Vasona Park is a park located in Los Gatos, California; Shutterstock ID 110237099; Purchase Order: -

Vasona Lake County Park

3.5/5(3 reviews)

Vasona Lake County Park is just one of the places to see in Los Gatos, so why not enjoy the other things to explore during your travels? Discover the mountain views and shops in this family-friendly area.

Vasona Lake County Park
Vernal falls along the Mist Trail in Yosemite National Park in autumn

Castle Rock Falls

Enjoy the mountain views and explore Castle Rock Falls, a lovely green space in Los Gatos. Check out the shops and wineries in this family-friendly area.

Castle Rock Falls
Regale Winery and Vineyards

Regale Winery and Vineyards

You can enjoy a tasting or tour at Regale Winery and Vineyards during your travels to Los Gatos. Amble around this family-friendly area's beautiful beaches, or seek out the biking trails.

Regale Winery and Vineyards

What to do in Redwood Estates

Santa Cruz Beach Hill to Mission Hill Loop Via Downtown

Beach Hill to Historic Downtown Santa Cruz Loop

$45
per adult
Beach Hill to Historic Downtown Santa Cruz Loop
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
See all activities in Redwood Estates

Redwood Estates Hotel Deals

Dream Inn Santa Cruz

Dream Inn Santa Cruz

4 out of 5
175 W Cliff Dr Santa Cruz CA
Fully refundableReserve now, pay when you stay
$246 nightly
The price is $280 total per night from May 21 to May 22
$280 total
May 21 - May 22
Total with taxes and fees
9.4/10 Exceptional! (1,010 reviews)
"Beautiful hotel, perfect walking location to pier and wharf"

Reviewed on May 18, 2026

Dream Inn Santa Cruz
Maple Tree Inn

Maple Tree Inn

3 out of 5
711 E El Camino Real Sunnyvale CA
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $95 total per night from May 29 to May 30
$95 total
May 29 - May 30
Total with taxes and fees
9/10 Wonderful! (2,745 reviews)
"I stayed there over a week ago and they still haven’t returned my deposit. I’ve tried to call them and the phone call won’t go through I’m really upset. I need my money."

Reviewed on May 18, 2026

Maple Tree Inn
Hyatt Place San Jose Airport

Hyatt Place San Jose Airport

3 out of 5
82 Karina Court, Airport San Jose CA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $127 total per night from May 29 to May 30
$127 total
May 29 - May 30
Total with taxes and fees
9/10 Wonderful! (1,578 reviews)
"Please dont give regular guest handicap rooms shower heads are not built for us"

Reviewed on May 19, 2026

Hyatt Place San Jose Airport
See all 2,548 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 $656 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.