Redwood Oaks Vacations from $416

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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 Oaks Vacation

Your next big journey is just around the corner with a vacation package to Redwood Oaks. Entertainment, relaxation and nonstop good times — you're sure to find it in this neighborhood. Make time for sightseeing on your trip to Redwood Oaks. Pencil in visits to popular nearby attractions such as Woodside Central Shopping Center and Nazareth Ice Oasis. Don't just think about it — turn it into a reality! Secure your ideal Redwood Oaks vacation with Expedia and enjoy traveling your way.

The Latest Redwood Oaks Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Bel Abri Napa Valley Inn

Bel Abri Napa Valley Inn

Central Napa
Save 100% on your flight
$416
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Oakland (OAK)
9.6/10 Exceptional! (1,003 reviews)
Clean. Comfortable. Spacious. an exceptional value in the heart of Napa.

Reviewed on Sep 21, 2026

Duchamp Healdsburg

Duchamp Healdsburg

Save 100% on your flight
$1,376
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
San Diego (SAN) to San Francisco (SFO)
9.4/10 Exceptional! (98 reviews)
Cavallo Point

Cavallo Point

Save 100% on your flight
$539
per person
Nov 12 - Nov 14
found 1 day ago
Roundtrip flight included
San Diego (SAN) to San Francisco (SFO)
9.2/10 Wonderful! (1,002 reviews)
Fairmont Sonoma Mission Inn & Spa

Fairmont Sonoma Mission Inn & Spa

Boyes Hot Springs
Save 100% on your flight
$774
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Oakland (OAK)
8.8/10 Excellent! (1,003 reviews)
Aqua Breeze Inn

Aqua Breeze Inn

Westside Santa Cruz
Save 100% on your flight
$526
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to San Jose (SJC)
8.2/10 Very Good! (1,005 reviews)
This property is very dated, it was fairly clean but, very old hotel. Also, did not like Santa Cruz at all. Drive a few miles further south and stay in Capitola!!

Reviewed on Sep 24, 2026

Where to stay in Redwood Oaks

Find the best Redwood Oaks areas and neighborhoods for the activities you enjoy most. Learn more about Redwood Oaks
A marina with various boats docked, including a yellow and white boat named 'Golden Gate'.

Fisherman's Wharf

1 out of top 10 points of interest in this area

Discover Pier 39, Ghirardelli Square, and the San Francisco Maritime National Historical Park in this bustling tourist hotspot. Savor seafood at family-owned restaurants and explore the sea lion colony, while enjoying convenient cable car access.

A cityscape with tall buildings, palm trees, and red double-decker buses.

Union Square

Major tourist destination in downtown San Francisco, Union Square boasts shopping, hotels, and theaters. Explore department stores, boutiques, and galleries, or catch a performance at various theaters. Enjoy the Dewey Monument and stunning views from nearby hotels. Easily accessible via cable car lines, buses, and subway systems.

A trolley on a street with buildings and a clock tower.

Downtown San Francisco

3 out of top 10 points of interest in this area

Serving as San Francisco's central business district, this area boasts Northern California's two tallest buildings, the Salesforce Tower and Transamerica Pyramid. Explore shopping malls like the Embarcadero Center and enjoy parks such as Sue Biermann Park, all easily accessible via Muni bus and rail lines.

A cityscape with modern skyscrapers, a central park with pathways, and a few people walking.

South of Market

From baseball games to top-notch art exhibits, find endless entertainment in one of San Francisco’s fastest-growing neighborhoods.

A cityscape with a prominent skyscraper, a bridge, and a mix of modern and historic buildings.

Nob Hill

Luxury hotels, historic mansions, and Michelin-starred restaurants abound in this upscale area. Explore Union Square shopping district, Grace Cathedral, and the SF Masonic Auditorium for a taste of culture and history.

Stay near popular Redwood Oaks attractions

Woodside Central Shopping Center

8.2/10 (66 reviews)
You can find the perfect gifts to bring home at Woodside Central Shopping Center during your stay in Redwood City. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties