Midtown Vacations from $527

Book a Hotel + Flight or Car together to unlock savings

The Latest Midtown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Chaminade Resort & Spa

Chaminade Resort & Spa

4 out of 5
Save 100% on your flight
Price was $708, price is now $527 per person
$527
per person
Nov 14 - Nov 16
found 13 hours ago
Roundtrip flight included
Portland (PDX) to San Jose (SJC)
8/10 Very Good! (1,006 reviews)
Photos on Expedia definitely made this property seem much nicer than it was.

Reviewed on Aug 29, 2025

Aqua Breeze Inn

Aqua Breeze Inn

2.5 out of 5
Westside Santa Cruz
Price was $2,939, price is now $1,353 per person
$1,353
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to San Jose (SJC)
8/10 Very Good! (1,003 reviews)
Short walk to Boardwalk great views

Reviewed on Aug 25, 2025

Motel 6 Santa Cruz, CA

Motel 6 Santa Cruz, CA

2 out of 5
Westside Santa Cruz
Save 100% on your flight
Price was $1,631, price is now $1,094 per person
$1,094
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to San Jose (SJC)
5.8/10 (535 reviews)
Place was good because the Area was ok and somewhat of a walking distance to the boardwalk. Entrance door or door frame had massive gap on top and bottom.

Reviewed on Sep 2, 2025

Shashi Hotel Mountain View Palo Alto

Shashi Hotel Mountain View Palo Alto

5 out of 5
Save 100% on your flight
Price was $774, price is now $531 per person
$531
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to San Jose (SJC)
9.4/10 Exceptional! (1,007 reviews)
We liked the style of everything. Everything was clean and minimalist but modern. The staff was polite and helpful. The AC didn't seem to be controllable. And it worked sub par. Again the scene was nice. It was perfectly located for comfortable walking distance to the Shoreline Ampiatheater. The hotel menu could use better choices. Maybe too fancy for me but mousse liver before heading out was not going to be enough 😭

Reviewed on Sep 1, 2025

La Bahia Hotel and Spa

La Bahia Hotel and Spa

3.5 out of 5
Westside Santa Cruz
Save 100% on your flight
Price was $788, price is now $574 per person
$574
per person
Nov 14 - Nov 16
found 13 hours ago
Roundtrip flight included
Portland (PDX) to San Jose (SJC)
No reviews

Where to stay in Midtown

Find the best Midtown areas and neighborhoods for the activities you enjoy most. Learn more about Midtown
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

Midtown Hotel Deals

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
$137 nightly
The price is $158 total per night from Oct 1 to Oct 2
$158 total
Oct 1 - Oct 2
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Santa Cruz
Ocean Pacific Lodge

Ocean Pacific Lodge

2 out of 5
301 Pacific Avenue, Santa Cruz, CA
$104 nightly
The price is $120 total per night from Sep 23 to Sep 24
$120 total
Sep 23 - Sep 24
Total with taxes and fees
Ocean Pacific Lodge
Chaminade Resort & Spa

Chaminade Resort & Spa

4 out of 5
1 Chaminade Ln, Santa Cruz, CA
Fully refundableReserve now, pay when you stay
$223 nightly
The price is $250 total per night from Sep 14 to Sep 15
$250 total
Sep 14 - Sep 15
Total with taxes and fees
7.8/10 Good! (980 reviews)
"Nice, but slightly overpriced"

Reviewed on Aug 26, 2025

Chaminade Resort & Spa
See all 1,199 properties in Midtown
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 Midtown

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
5-Hour Wilderness Skills & Survival Clinic

5-Hour Wilderness Skills & Survival Clinic

$139
per adult
5-Hour Wilderness Skills & Survival Clinic
Santa Cruz Redwoods Forest Therapy

Santa Cruz Redwoods Forest Therapy

$85
per adult
Santa Cruz Redwoods Forest Therapy
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.