Circles Vacations from $546

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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.
Sonesta Silicon Valley

Sonesta Silicon Valley

4 out of 5
Save 100% on your flight
per person
Aug 10 - Aug 16
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Jose (SJC)
9/10 Wonderful! (1,510 reviews)
Very quiet and clean

Reviewed on Jun 27, 2025

Aqua Breeze Inn

Aqua Breeze Inn

2.5 out of 5
Westside Santa Cruz
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Ontario (ONT) to San Jose (SJC)
8/10 Very Good! (1,008 reviews)
Clean and very close to the boardwalk

Reviewed on Jul 1, 2025

@ Marbella Lane - 3BR Designer Near Valley Fair

@ Marbella Lane - 3BR Designer Near Valley Fair

3 out of 5
Save 100% on your flight
per person
Aug 1 - Aug 8
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) to San Jose (SJC)
No reviews
Chaminade Resort & Spa

Chaminade Resort & Spa

4 out of 5
Save 100% on your flight
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Ontario (ONT) to San Jose (SJC)
8/10 Very Good! (1,003 reviews)
Beautiful views, nice hiking trails, pools, hot tubs, sauna, steam bath, spa services. Really wonderful place to relax, we enjoyed it thoroughly.

Reviewed on Jun 30, 2025

Sonesta San Jose - Milpitas

Sonesta San Jose - Milpitas

3.5 out of 5
Save 100% on your flight
per person
Aug 10 - Aug 16
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Jose (SJC)
8.4/10 Very Good! (1,003 reviews)
Room is clean. Greatly appreciated Javier’s excellent assistance when i was check-in on 6/25. The location is easy to access highway or nearby destinations. Some great Asian food restaurants are just across street with walking distance. Highly recommended!

Reviewed on Jun 26, 2025

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 Santa Cruz Beach Boardwalk and Monterey Bay, 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
$169 nightly
The price is $194 total per night from Jul 6 to Jul 7
$194 total
Jul 6 - Jul 7
Total includes taxes and fees
8.4/10 Very Good! (1,012 reviews)
"Loved the bar"

Reviewed on Jun 29, 2025

Hotel Paradox, Autograph Collection
Dream Inn Santa Cruz
Dream Inn Santa Cruz
4 out of 5
175 W Cliff Dr, Santa Cruz, CA
$319 nightly
The price is $362 total per night from Jul 7 to Jul 8
$362 total
Jul 7 - Jul 8
Total includes taxes and fees
9.2/10 Wonderful! (1,006 reviews)
"Location is perfect for a weekend at the beach!"

Reviewed on Jun 29, 2025

Dream Inn Santa Cruz
Courtyard by Marriott Santa Cruz
Courtyard by Marriott Santa Cruz
3 out of 5
313 Riverside Avenue, Santa Cruz, CA
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $194 total per night from Jul 6 to Jul 7
$194 total
Jul 6 - Jul 7
Total includes taxes and fees
8.2/10 Very Good! (842 reviews)
"The hotel location is fantastic if the Boardwalk is your focus, literally one block away. The room was large with a sitting area. We traveled with our two kids and the sofa bed was useful. There was enough space for a twin blowup mattress too. There's a pool, although we didnt use but saw olentyy ..."

Reviewed on Jun 25, 2025

Courtyard by Marriott Santa Cruz
See all 1,152 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

4.5/5(2,013 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.

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

Mystery Spot

4/5(639 reviews)

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

4.5/5(85 reviews)

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

Beginner Surf Lesson in Santa Cruz

Beginner Surf Lesson in Santa Cruz

$129
per adult
Beginner Surf Lesson in Santa Cruz
Santa Cruz Redwoods Forest Therapy

Santa Cruz Redwoods Forest Therapy

$85
per adult
Santa Cruz Redwoods Forest Therapy
Bay Area Rock Climbing

Beginner Outdoor Rock Climbing - Bay Area

$119
per adult
Beginner Outdoor Rock Climbing - Bay Area
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.