A vineyard with rows of grapevines.

Santa Cruz Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

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

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

Top Santa Cruz vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Sept 24 - Sept 27

    Hotel Panamericano + Flight

    Downtown Santiago
    2 nights
    3.0 star property
    8.6/10 - Excellent (233 reviews)
    "Excelente hotel"
    Reviewed July 24, 2026
    Roundtrip Toronto (YTO) - Santiago (SCL)
    YYZ - SCL2 stops SCL - YYZ2 stops
    CA $1,089
    CA $1,005
    per traveller
    found 1 day ago
    Hotel Panamericano
  • Sept 24 - Sept 27

    Aubrey Hotel Boutique + Flight

    Bellavista
    2 nights
    4.0 star property
    9.4/10 - Exceptional (151 reviews)
    "Room was excellent. Had a problem at checkout. Major language barrier"
    Reviewed February 18, 2026
    Roundtrip Toronto (YTO) - Santiago (SCL)
    YYZ - SCL2 stops SCL - YYZ2 stops
    CA $1,236
    CA $1,073
    per traveller
    found 1 day ago
    Aubrey Hotel Boutique
  • Sept 24 - Sept 27

    Hotel Sommelier Agustinas + Flight

    Downtown Santiago
    2 nights
    3.0 star property
    8.6/10 - Excellent (256 reviews)
    "Good location for visiting the sights of the central city. The room was very spacious, with a small kitchen and living space separate from the bedroom. The breakfast had a good range and was well stocked. The rooftop bar was a good spot for a refreshment after a day exploring the sights. The only negative was that our we could hear the noise from the bar in our 5th floor room."
    Reviewed May 12, 2026
    Roundtrip Toronto (YTO) - Santiago (SCL)
    YYZ - SCL2 stops SCL - YYZ2 stops
    CA $1,128
    CA $1,007
    per traveller
    found 1 day ago
    Hotel Sommelier Agustinas
  • Sept 24 - Sept 27

    Casa Bueras Boutique Hotel + Flight

    Downtown Santiago
    2 nights
    4.5 star property
    9.2/10 - Wonderful (552 reviews)
    "Excellent location. The room was spotless, spacious, and very comfortable. The interior design was impeccable, and the boutique hotel itself is absolutely beautiful. The breakfast was also excellent, with a great selection of delicious options."
    Reviewed August 3, 2026
    Roundtrip Toronto (YTO) - Santiago (SCL)
    YYZ - SCL2 stops SCL - YYZ2 stops
    CA $1,150
    CA $1,063
    per traveller
    found 1 day ago
    Casa Bueras Boutique Hotel
  • Sept 24 - Sept 27

    Hotel Boutique Castillo Rojo + Flight

    Bellavista
    2 nights
    4.0 star property
    9.6/10 - Exceptional (756 reviews)
    "Wonderful hotel! We absolutely loved our stay. The staff are the friendliest people and everyone was so kind and welcoming."
    Reviewed July 29, 2026
    Roundtrip Toronto (YTO) - Santiago (SCL)
    YYZ - SCL2 stops SCL - YYZ2 stops
    CA $1,159
    CA $1,071
    per traveller
    found 1 day ago
    Hotel Boutique Castillo Rojo

Discover the most popular places to visit in Santa Cruz

What to do in Santa Cruz

Santa Cruz Hotel Deals

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.

Frequently Asked Questions

How much does a Santa Cruz vacation package cost?

You can pick up a vacation package to this popular destination from CA $1,005 on Expedia. However, how much your vacation to Santa Cruz costs will depend on the length of stay, season and hotel choice.

What are the cheapest months to go to Santa Cruz?

You can usually find lower rates and better availability in May, July and September. Check out our cheap Santa Cruz vacation packages and you could land some excellent off-season deals.

How many days is enough for Santa Cruz?

Usually, a handful of days is enough for a Santa Cruz vacation. With a carefully crafted itinerary, you can visit all the leading attractions such as Laura Hartwig Winery, as well as explore some hidden treasures along the way.

Is it worth booking a vacation package to Santa Cruz?

Santa Cruz has everything you need for the perfect break — history, culture and festivals are just the start. Whether you want to visit sights like Plaza de Armas and Museo de Colchagua, or take the path less travelled, you'll have plenty to explore on your Santa Cruz vacation.

How to find the best Santa Cruz package deals?

Use Expedia's filters to help you find some of the best Santa Cruz package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Santa Cruz package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.

Is it cheaper to book a Santa Cruz vacation as a package?

Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component separately. And you'll still get the flexibility to create a customized Santa Cruz vacation by choosing your preferred accommodation type, airline and car class.

When to book a vacation package to Santa Cruz?

If you've got your Santa Cruz travel dates locked in, book as early as you can to score some fantastic deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for setting off on a whim.

How to plan a trip to Santa Cruz?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Santa Cruz.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and food to airfares and activities. Your hotel will likely be the biggest expense during your trip to Santa Cruz.
  3. Work out your trip length: Think about how long you'd like to spend exploring Santa Cruz. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodations: Once you've nailed down your dates and duration, lock in the right Santa Cruz vacation package for you.