Cupertino Vacation Packages
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Your Cupertino Vacation
A great way to experience this interesting city is with a customized Cupertino vacation package. Stay in the neighborhood of South San Jose, which is good for culture, golfing and mountain biking or go someplace else — our packages are all about you. Fill your itinerary with tours of Californias Great America, Winchester Mystery House and Santa Clara University, some of the attractions you simply have to see during a trip to Cupertino. Your ideal Cupertino vacation is just a few clicks away. Explore accommodations, flights and more on Expedia for a getaway that's tailored just for you.
Top Cupertino Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Motel 6 Santa Cruz, CA
Westside Santa Cruz
Price was CA $3,291, price is now CA $2,244 per person
CA $2,244
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to San Jose (SJC)
6/10 (581 reviews)
The room was dirty and I'm very sure the bed sheets/blankets washed.
Reviewed on Nov 15, 2025
Cliff Crest Bed & Breakfast
Westside Santa Cruz
Price was CA $2,392, price is now CA $1,662 per person
CA $1,662
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to San Jose (SJC)
8.2/10 Very Good! (73 reviews)
It was a great stay , the couple that runs it , Constantine and Adriana are awesome , it was a great room and a good breakfast, will be back,
Reviewed on Dec 28, 2025
La Bahia Hotel and Spa
Westside Santa Cruz
Price was CA $3,070, price is now CA $2,332 per person
CA $2,332
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to San Jose (SJC)
9.6/10 Exceptional! (44 reviews)
Great amenities, very comfortable beds, and beautiful property!
Reviewed on Feb 2, 2026
Capitola Venetian Hotel
Price was CA $2,661, price is now CA $2,028 per person
CA $2,028
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to San Jose (SJC)
8.6/10 Excellent! (775 reviews)
There was no one at front desk when I got there just after 7 p.m. I had to call and wait for someone to come. However, the person who checked me in after arriving. Was, very courteous, accommodating, and professiona. The bathtub didn’t have a stopper, though. So, I had to improvise to block the water from draining. Just to have a bath. But, I did receive a Much larger than one I booked. Which was a nice surprise! Of course, the location of the hotel is amazing! Beautiful area. And, I got a late checkout which was very nice! I give 4.5 stars. Enjoyed my stay.
Reviewed on Feb 6, 2026
Cupertino Hotel Deals
Aloft Cupertino
10165 N De Anza Blvd Cupertino CA
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Feb 20 to Feb 21
CA $140
CA $157 total
Feb 20 - Feb 21
includes taxes & fees
8.6/10 Excellent! (1,017 reviews)
A
Reviewed on Feb 5, 2026
Hilton Garden Inn Cupertino
10741 N Wolfe Rd Cupertino CA
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Feb 14 to Feb 15
CA $167
CA $187 total
Feb 14 - Feb 15
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Staff is amazing! Coffee in the lobby in the morning. The room was clean. The food was so so.
Reviewed on Feb 5, 2026
Juniper Hotel Cupertino, Curio Collection by Hilton
10050 S De Anza Blvd Cupertino CA
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Feb 27 to Feb 28
CA $148
CA $166 total
Feb 27 - Feb 28
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Room, food, staff. All great
Reviewed on Feb 2, 2026
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.
What to do in Cupertino
San Jose Ghost Tour: The Scythe, Sacrifice, & Silhouette
CA $44
per adult
The Escape Game San Jose: Epic 60-Minute Adventure at Valley Fair
CA $64
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
