Circles Vacations from $355

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Your Circles Vacation

Booking a Circles vacation package is a good way to know the ins and outs of this neighborhood. From its must-see spots to its little-known secrets, you won't be short of adventures. Your trip to Circles wouldn't be complete without a visit to popular attractions nearby such as Santa Cruz Beach Boardwalk, University of California, Santa Cruz and Natural Bridges State Park. Expedia will help put your travel plans into action. Book your perfect Circles vacation now.

The Latest Circles Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott Fremont Silicon Valley

Residence Inn by Marriott Fremont Silicon Valley

3 out of 5
Glenmoor
Price was $487, price is now $355 per person
$355
per person
Feb 14 - Feb 18
found 16 hours ago
Roundtrip flight included
Chicago (CHI) to San Jose (SJC)
8.4/10 Very Good! (368 reviews)
Gym missing all weights below 30#. Had tread mills. No weight machines just a bench.

Reviewed on Sep 25, 2025

@ Marbella Lane - 3BR Designer Near Valley Fair

@ Marbella Lane - 3BR Designer Near Valley Fair

3 out of 5
Save 100% on your flight
Price was $2,063, price is now $1,301 per person
$1,301
per person
Feb 7 - Feb 9
found 15 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to San Jose (SJC)
No reviews
Holiday Inn San Jose - Silicon Valley by IHG

Holiday Inn San Jose - Silicon Valley by IHG

3 out of 5
Rosemary
Save 100% on your flight
Price was $1,404, price is now $1,004 per person
$1,004
per person
Feb 1 - Feb 6
found 13 hours ago
Roundtrip flight included
Chicago (CHI) to San Jose (SJC)
8.2/10 Very Good! (1,107 reviews)
Hotel was clean, nice lobby. My only beef is not getting a receipt emailed to me by hotel or Expedia, forcing me to track it down.

Reviewed on Nov 24, 2025

Global Luxury Suites San Jose Downtown

Global Luxury Suites San Jose Downtown

4 out of 5
Downtown San Jose
Save 100% on your flight
Price was $964, price is now $695 per person
$695
per person
Jan 16 - Jan 19
found 16 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to San Jose (SJC)
6.6/10 (29 reviews)
The room was in good condition, amenities were fine. Biggest issue was the location of the room to San Pedro Square. Unless the windows and doors are replaced there is a major noise issue in this unit - every night of the week there is live music, on Thurs-Sat there is music until 2:00am. This is very impactful to sleep

Reviewed on Oct 28, 2025

SpringHill Suites by Marriott San Jose Airport

SpringHill Suites by Marriott San Jose Airport

3 out of 5
Rosemary
Price was $535, price is now $388 per person
$388
per person
Jan 16 - Jan 19
found 16 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to San Jose (SJC)
9.2/10 Wonderful! (1,002 reviews)
Nice clean hotel with a comfortable bed.A little difficult to find. Not a fan of the room layout with the clear glass doors. If someone uses the bathroom at night, it lights up the whole bedroom.

Reviewed on Oct 23, 2025

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Limited-time deals: Save up to 50% on select hotels.
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Where to stay in Circles

Find the best Circles areas and neighborhoods for the activities you enjoy most. Learn more about Circles
Santa Cruz showing general coastal views and views as well as an individual male

Westside Santa Cruz

7 out of top 10 points of interest in this area
4/5(2,586 area reviews)

Westside Santa Cruz is known for its stunning beaches, and with sights like Monterey Bay and Pacific Avenue, you won't get bored spending a day wandering around this part of Santa Cruz.

Find hotels in Westside Santa Cruz

Circles Hotel Deals

Hotel Paradox, Autograph Collection

Hotel Paradox, Autograph Collection

4 out of 5
611 Ocean St Santa Cruz CA
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $126 total per night from Dec 3 to Dec 4
$126 total
Dec 3 - Dec 4
Total with taxes and fees
8.6/10 Excellent! (1,128 reviews)
Clean rooms, great stay, nice amenities, courteous staff, restaurant food fresh and tasty!

Reviewed on Nov 26, 2025

Hotel Paradox, Autograph Collection
La Quinta Inn & Suites by Wyndham Santa Cruz

La Quinta Inn & Suites by Wyndham Santa Cruz

3 out of 5
550 2nd St Santa Cruz CA
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $132 total per night from Dec 7 to Dec 8
$132 total
Dec 7 - Dec 8
Total with taxes and fees
9.2/10 Wonderful! (1,237 reviews)
Great location and both the rooms and facility very clean. When we did use the TV, channel selection not good. Better off just remove the TV.

Reviewed on Nov 29, 2025

La Quinta Inn & Suites by Wyndham Santa Cruz
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
$249 nightly
The price is $284 total per night from Dec 3 to Dec 4
$284 total
Dec 3 - Dec 4
Total with taxes and fees
9.2/10 Wonderful! (1,006 reviews)
Gorgeous view! Clean room, nice staff, location right on the beach, pool, hot tub.

Reviewed on Nov 29, 2025

Dream Inn Santa Cruz
See all 1,146 properties in Circles
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

Discover the most popular places to visit in Circles

Another beautiful sunset 🌇

Santa Cruz Beach Boardwalk

Enjoy the thrill rides with your kiddos at Santa Cruz Beach Boardwalk as part of your trip to Santa Cruz. Attend a sporting event in this walkable area, or seek out the biking trails.

Santa Cruz Beach Boardwalk
The place where you can't stay straight.

Mystery Spot

Find out about the history of Santa Cruz with a stop at Mystery Spot. Attend a sporting event in this walkable area, or seek out the surfing spots.

Mystery Spot
Santa Cruz Wharf

Santa Cruz Wharf

Explore the waterfront of Santa Cruz Wharf and enjoy activities such as surfing in Santa Cruz. Attend a sporting event in this walkable area, or seek out the biking trails.

Santa Cruz Wharf

Things to do

Rock Climbing 2 - Beyond the Basics

Outdoor Rock Climbing - Level 2

$119
per adult
Outdoor Rock Climbing - Level 2
Beginner Surf Lesson in Santa Cruz

Beginner Surf Lesson in Santa Cruz

$129
per adult
Beginner Surf Lesson in Santa Cruz
5-Hour Wilderness Skills & Survival Clinic

5-Hour Wilderness Skills & Survival Clinic

$139
per adult
5-Hour Wilderness Skills & Survival Clinic
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.