Circles Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Circles

Price found within the past 48 hours. Click for updated prices.
Aqua Breeze Inn

Aqua Breeze Inn

2.5 out of 5
Westside Santa Cruz
Price was CA $1,191, price is now CA $866 per person
CA $866
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to San Jose (SJC)
8/10 Very Good! (1,002 reviews)
Nice people. Easy location. Comfy beds.

Reviewed on Feb 6, 2026

@ Marbella Lane - 4BR Siliconvalley Gempool House

@ Marbella Lane - 4BR Siliconvalley Gempool House

3 out of 5
Berryessa
Price was CA $3,527, price is now CA $2,566 per person
CA $2,566
per person
Apr 5 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to San Jose (SJC)
No reviews
@ Marbella Lane - Elegant Home in SJ

@ Marbella Lane - Elegant Home in SJ

3 out of 5
Willow Glen
Price was CA $2,656, price is now CA $1,981 per person
CA $1,981
per person
Apr 5 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to San Jose (SJC)
No reviews
@ Marbella Lane - Alluring & Spacious 3BR Home

@ Marbella Lane - Alluring & Spacious 3BR Home

3 out of 5
Cambrian
Price was CA $2,327, price is now CA $1,742 per person
CA $1,742
per person
Apr 5 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to San Jose (SJC)
No reviews
Shashi Hotel Mountain View Palo Alto

Shashi Hotel Mountain View Palo Alto

5 out of 5
Price was CA $1,284, price is now CA $997 per person
CA $997
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to San Jose (SJC)
9.4/10 Exceptional! (1,297 reviews)
Clean room and staff were friendly and prepared to make our stay comfortable. The robes and slippers added to the comfort. Highly recommend this hotel.

Reviewed on Feb 20, 2026

Where to stay in Circles

Find the best Circles areas and neighborhoods for the activities you enjoy most. Learn more about Circles
This is a small state park at the northern end of Santa Cruz' scenic West Cliff Drive and a little over a mile from the Boardwalk, wharf and Main Beach. A couple of times a year you can see Monarch butterflies during their migration. They are not in the numbers of years past, but you'll still see some. If you walk north towards the rocks during low tide you will find some amazing tidepools full of sea anenomes, sea urchins, starfish, crabs, hermit crabs, and all sorts of marine life. The tidepools are on a ledge, so the tide needs to be quite high

Westside Santa Cruz

7 out of top 10 points of interest in this area
4/5(34 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

Seacliff Inn Aptos, Tapestry Collection by Hilton

Seacliff Inn Aptos, Tapestry Collection by Hilton

3.5 out of 5
7500 Old Dominion Court Aptos CA
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Mar 31 to Apr 1
CA $164
CA $190 total
Mar 31 - Apr 1
includes taxes & fees
8.6/10 Excellent! (1,086 reviews)
No. Room had spider net on ceiling and corners and dust on AC unit also had bad smell when unit started to run.

Reviewed on Mar 2, 2026

Seacliff Inn Aptos, Tapestry Collection by Hilton
Chaminade Resort & Spa

Chaminade Resort & Spa

4 out of 5
1 Chaminade Ln Santa Cruz CA
Fully refundableReserve now, pay when you stay
8.2/10 Very Good! (1,008 reviews)
It is a really great place to feel you're escaping the rigours of life.

Reviewed on Mar 2, 2026

Get rates
Chaminade Resort & Spa
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
The price is CA $142 per night from Mar 5 to Mar 6
CA $142
CA $165 total
Mar 5 - Mar 6
includes taxes & fees
8.6/10 Excellent! (1,224 reviews)
The rooms need a lot of help. The fact that they have pets allowed in the rooms, makes it feel dirty. They try to make it feel current and clean by having laminate floors, which in turn makes it feel old and dirty instead. The rooms are not cozy at all. The bed was comfortable, the staff was nice. ...

Reviewed on Mar 2, 2026

Hotel Paradox, Autograph Collection
See all 1,167 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
Family Vacations
Family Vacations

Frequently asked questions

How much does a Circles vacation package cost?
Starting from only CA $866, a package is your portal to low-priced travel. Create your own Circles trip by picking from our wide range of airfares, hotels and rental cars.
How do I get a cheap travel package to Circles?
Browse and lock in everything in one place with our Circles vacation packages. You'll find deals on hotels, flights and more that'll keep your bank account happy and adventurous side satisfied. And, with more than 550 partner airlines and 1,000,000 properties worldwide to pick from, you have countless opportunities to mix and match your own way.
Where should I stay in Circles?
Take the leg work out of sightseeing by staying right around the corner from Circles's iconic attractions. Santa Cruz Beach Boardwalk and Mystery Spot are two visitor favorites.
How far in advance should I book my Circles vacation?
While not all airlines release tickets early, it's usually possible to compare international flights on Expedia up to a year in advance. This is the time you'll bag some incredible bargains. If you've left things to the last minute, there's a chance you could get lucky. Sometimes the lowest prices emerge only weeks before departure.
What does an Expedia Circles travel package include?
Expedia has all you need to lock in Circles getaway, but what goes into your package is up to you. Choose from any combination of rental cars, hotels and flights. Searching for a few activities to keep you on the move? Once you've made your booking, you can add them on too. No matter your style or budget, there's a deal to meet your needs.
What should I know before booking a Circles travel package?
Our prices are already low. However, you'll score even more bargains if you book your flights, hotels and car rentals together. With an Expedia package, you'll always get transparent pricing and lots of choice.
Can I choose my airline with a Circles Expedia vacation package?
With a vacation package, you're the boss. Whether you'd like to fly to Circles in business or coach, simply select from the available airline options. Expedia has access to over 550 airline partners throughout the world.
If I'm not able to travel, can I cancel my Circles vacation package?
Yes, you can cancel your Circles booking if your travel plans have changed. Whether you'll incur a penalty or not depends on your airline, hotel or car rental company. You may be able to cancel or change free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Circles

Gotta ride this 100 year old wooden roller Coaster on the Santa Cruz Beach Boardwalk

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
Sunrise at Walton Lighthouse

Santa Cruz Harbor

Explore the waterfront in Santa Cruz with a trip to Santa Cruz Harbor. While you're in the area, stroll along the beautiful beaches.

Santa Cruz Harbor
T4D055 Sunset, Cowell Beach, Santa Cruz, California, United States

Cowell's Beach

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

Cowell's Beach

Things to do

Self Guided UC Santa Cruz Walking Tour: Unlock Secret Stories

UC Santa Cruz: Personalized Self-Guided App Tour

CA $7
per traveller
UC Santa Cruz: Personalized Self-Guided App Tour
Capitola Private 2-Hour Walking Tour

Capitola Private Personalized Self-Guided App Tour

CA $7
per traveller
Capitola Private Personalized Self-Guided App Tour
Meet Capitola Wine Bar owners!

Capitola Friday Night Food Tour

CA $177
per adult
100% of travellers recommend
Capitola Friday Night Food Tour
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.