Midtown Vacations from $273

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The Latest Midtown Vacation Packages

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

Sonesta San Jose - Milpitas

Save 100% on your flight

$273

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to San Jose (SJC)

8.8/10 Excellent! (1,088 reviews)

@ Marbella Lane - 4BR Siliconvalley Gempool House

Berryessa

Save 100% on your flight

$1,988

per person

Nov 8 - Nov 14

found 1 day ago

Roundtrip flight included

San Diego (SAN) to San Jose (SJC)

No reviews

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

Save 100% on your flight

$1,677

per person

Nov 8 - Nov 14

found 1 day ago

Roundtrip flight included

San Diego (SAN) to San Jose (SJC)

No reviews

Aqua Breeze Inn

Westside Santa Cruz

Save 100% on your flight

$506

per person

Oct 30 - Nov 2

found 17 hours 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

Save 100% on your flight

$979

per person

Oct 26 - Oct 30

found 9 hours ago

Roundtrip flight included

Seattle (SEA) 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

A coastal cityscape with a beach, pier, and amusement park.

Westside Santa Cruz

6 out of top 10 points of interest in this area

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.

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.

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.

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.

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.

Midtown Hotel Deals

La Bahia Hotel and Spa

215 Beach Street Santa Cruz CA

Fully refundableReserve now, pay when you stay

$296 nightly

$332 total

Sep 9 - Sep 10

Total with taxes and fees

9.6/10 Exceptional! (465 reviews)

"Super charming classic hotel with a friendly staff, great pool and jacuzzi. Awesome views from the balcony. Just wish it wasn't so extremely expensive"

Reviewed on Sep 4, 2026

Chaminade Resort & Spa

1 Chaminade Ln Santa Cruz CA

Fully refundableReserve now, pay when you stay

$219 nightly

$250 total

Sep 7 - Sep 8

Total with taxes and fees

Bay Front Inn Santa Cruz

325 Pacific Ave Santa Cruz CA

Fully refundableReserve now, pay when you stay

$73 nightly

$86 total

Sep 10 - Sep 11

Total with taxes and fees

7.4/10 Good! (1,011 reviews)

"Place has a great location easy walk to boardwalk. Very affordable. Be aware more rooms than parking spots. If you want to check in early before 3 it will cost $25 and that's if the girl will open the door even if she sees you. There was a line of people waiting to check in around 6 and she wouldnt ..."

Reviewed on Sep 4, 2026

See all 1,244 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.