Westside Santa Cruz Vacations from $245

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 Westside Santa Cruz Vacation

Book a vacation package to Westside Santa Cruz and enjoy the best of what this picturesque neighborhood has to offer. Noted for its walking, cafes and dining, your next awesome adventure is waiting for you here. Wondering where to go during your trip to Westside Santa Cruz? Nearby attractions such as Santa Cruz Beach Boardwalk, University of California, Santa Cruz and Natural Bridges State Park are great places to start. Expedia can help turn your dream Westside Santa Cruz vacation into reality, no matter your budget or travel plans.

The Latest Westside Santa Cruz Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sonesta San Jose - Milpitas

Sonesta San Jose - Milpitas

$245
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to San Jose (SJC)
8.8/10 Excellent! (1,088 reviews)
Aqua Breeze Inn

Aqua Breeze Inn

Westside Santa Cruz
Save 100% on your flight
$506
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to San Jose (SJC)
8.2/10 Very Good! (1,011 reviews)
Great location. Pretty good overall for the price

Reviewed on Sep 1, 2026

Marbella Lane - 3BR Designer Near Valley Fair

Marbella Lane - 3BR Designer Near Valley Fair

Save 100% on your flight
$979
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Seattle (SEA) to San Jose (SJC)
No reviews
@ Marbella Lane - 4BR Siliconvalley Gempool House

@ Marbella Lane - 4BR Siliconvalley Gempool House

Berryessa
Save 100% on your flight
$1,650
per person
Oct 16 - Oct 19
found 7 hours ago
Roundtrip flight included
Burbank (BUR) to San Jose (SJC)
No reviews
@ Marbella Lane - SJ Designer Home 3BR Ldry+p

@ Marbella Lane - SJ Designer Home 3BR Ldry+p

Save 100% on your flight
$1,259
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Washington (DCA) to San Jose (SJC)
No reviews

Where to stay in Westside Santa Cruz

Find the best Westside Santa Cruz areas and neighborhoods for the activities you enjoy most. Learn more about Westside Santa Cruz
A rocky coastline with waves crashing against the rocks.

Eastside Santa Cruz

1 out of top 10 points of interest in this area

Eastside Santa Cruz is known for its beaches, and you can plan a trip to Monterey Bay and Twin Lakes State Beach while you're in town.

Find hotels in Eastside Santa Cruz
A crowded beach with numerous boats and people.

Pleasure Point

World-renowned surf spot with a strong surf culture, Pleasure Point offers picturesque ocean views along East Cliff Drive and a walkable path with separate bike lanes. Enjoy amenities at Pleasure Point Park and nearby 41st Ave commercial district.

Find hotels in Pleasure Point
A street with a clock tower, a tram, and a building with a sign.

Beach Hill - Beach Flats

Beach Hill - Beach Flats might not have many top sights, but Santa Cruz Beach Boardwalk and Santa Cruz Main Beach are two attractions nearby that you can check out.

Find hotels in Beach Hill - Beach Flats
A beach with people playing and walking.

Upper Seabright

When in Upper Seabright, you can plan a visit to Santa Cruz Beach Boardwalk and Santa Cruz Harbor, some noteworthy sights in the nearby area.

Find hotels in Upper Seabright
A historic building with a distinctive corner turret, surrounded by autumn-colored trees and a clear street.

Downtown Santa Cruz

Unique features of Downtown Santa Cruz include the beaches and restaurants. Make a stop by Pacific Avenue or Santa Cruz Museum of Art and History while you're exploring the area.

Find hotels in Downtown Santa Cruz

Westside Santa Cruz Hotel Deals

La Bahia Hotel and Spa

La Bahia Hotel and Spa

215 Beach Street Santa Cruz CA
Fully refundableReserve now, pay when you stay
$292 nightly
$327 total
Sep 8 - Sep 9
Total with taxes and fees
La Bahia Hotel and Spa
Bay Front Inn Santa Cruz

Bay Front Inn Santa Cruz

325 Pacific Ave Santa Cruz CA
Fully refundableReserve now, pay when you stay
$79 nightly
$93 total
Sep 8 - Sep 9
Total with taxes and fees
7.4/10 Good! (1,013 reviews)
"If your gonna bleach the room make sure to use air fresheners."

Reviewed on Sep 6, 2026

Bay Front Inn Santa Cruz
Seaside Inn & Suites

Seaside Inn & Suites

525 Ocean St Santa Cruz CA
Fully refundableReserve now, pay when you stay
$62 nightly
$72 total
Oct 6 - Oct 7
Total with taxes and fees
Seaside Inn & Suites
See all 1,257 properties in Westside Santa Cruz
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations
Gay Friendly Vacations
LGBTQ Friendly Vacations
LGBTQ Friendly Vacations
Adventure Vacations
Adventure Vacations
Vacations in Month
Where to go when
Where to go when
Honeymoon Vacations
Honeymoon Vacations
Mountain Vacations
Mountain Vacations
Fishing Vacations
Fishing Vacations
Adults Only Vacations
Adults Only Vacations
Waterpark Vacations
Waterpark Vacations
Scuba Diving Vacations
Scuba Diving Vacations
Yoga Vacations
Yoga Vacations
Cheap Vacations
Cheap Vacations
Solo Vacations
Solo Vacations

Stay near popular Westside Santa Cruz attractions

A pier with colorful cable cars, a beach, and a sign that reads "WORLD FAMOUS."
Photo by Adri VDM Photography

Santa Cruz Beach Boardwalk

8.8/10 (6,089 reviews)
Enjoy the thrills at Santa Cruz Beach Boardwalk and find out why people love this theme park in Santa Cruz. Attend a sporting event in this walkable area, or seek out the biking trails.
See properties
A pier extending into the ocean with a roller coaster in the background.

Santa Cruz Wharf

9.0/10 (2,069 reviews)
After visiting Santa Cruz Wharf, make a plan to see the other sights and activities in Santa Cruz. Attend a sporting event in this walkable area, or seek out the surfing spots.
See properties
A natural rock arch formation on a beach with calm waters reflecting the structure.

Natural Bridges State Park

9.0/10 (842 reviews)
You can take time to visit Natural Bridges State Park during your travels to Santa Cruz. Attend a sporting event in this walkable area, or seek out the biking trails.
See properties
A historic half-timbered building with a stone facade, surrounded by trees and a red brick sidewalk.

Ocean Street

8.6/10 (1,332 reviews)
During your visit to Santa Cruz, you can enjoy retail therapy at Ocean Street. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.
See properties
A street with a clock tower, a tram, and a building with a sign.

Pacific Avenue

8.6/10 (951 reviews)
During your visit to Santa Cruz, you can browse for the perfect souvenirs at Pacific Avenue. Wander the beautiful beaches in this family-friendly area.
See properties

University of California Santa Cruz Arboretum

8.4/10 (103 reviews)
Explore the lovely green spaces of University of California Santa Cruz Arboretum and enjoy the surfing in Santa Cruz. Attend a sporting event in this walkable area, or seek out the biking trails.
See properties

Santa Cruz Main Beach

9.0/10 (19 reviews)
Why not spend a lazy afternoon at Santa Cruz Main Beach during your trip to Santa Cruz? Attend a sporting event in this walkable area, or seek out the biking trails.
See properties

Monterey Bay National Marine Sanctuary Exploration Center

8.0/10 (4 reviews)
You can spend an afternoon studying the exhibits at Monterey Bay National Marine Sanctuary Exploration Center during your travels in Santa Cruz. Attend a sporting event in this walkable area, or seek out the surfing spots.
See properties

Things to do

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
Santa Cruz Walking Tour: Discover Downtown & Mission Hill

Santa Cruz Walking Tour: Discover Downtown & Mission Hill

$45
per adult
Santa Cruz Walking Tour: Discover Downtown & Mission Hill
Beginner Surfing Lesson - Pacifica or Santa Cruz

Beginner Surfing Lesson - Pacifica or Santa Cruz

$139
per adult
100% of travellers recommend
Beginner Surfing Lesson - Pacifica or Santa Cruz
See all activities in Santa Cruz
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.