A coastal town with a beach, rocky shoreline, and a hilly background.

O'Higgins Region Vacations & Trips from $882

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Your O'Higgins Region Vacation

See and do more with a vacation package to O'Higgins Region. Whether you're going for the culture, festivals, history, or something else, our package deals make travel planning simple. A trip to O'Higgins Region wouldn't be complete without exploring some of its best cities, starting with Santa Cruz. A couple of the top attractions here include Lapostolle Clos Apalta Winery and Casino Colchagua. Rancagua should also be on the itineraries of all O'Higgins Region travelers. Visitors to this exciting destination enjoy Parque Safari Chile and Reserva Nacional Rio Cipreses. Expedia has hotels, flights and whatever else you need to help you curate your own tailored O'Higgins Region vacation today.

Top destinations in O'Higgins Region

A coastal town with a beach, rocky shoreline, and a hilly background.
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Pichilemu

Pichilemu

The Latest O'Higgins Region Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A reception desk with a chandelier, a large window with multiple panes, and a wooden floor.
    Jan 11 - Jan 17

    Matildas Hotel Boutique + Flight

    Downtown Santiago
    6 nights
    3.5 star property
    9.4/10 - Exceptional (294 reviews)
    "It was a quiet retreat in one of my favourite city:) lovely staff, and fantastic architecture!"
    Reviewed September 26, 2026
    Roundtrip • San José (SJO) - Santiago (SCL)
    SJO - SCL • 1 stop SCL - SJO • 2 stops
    $1,123
    $882
    per traveler
    found 1 day ago
    Matildas Hotel Boutique
  • A well-lit building with a pool in front, surrounded by greenery.
    Jan 17 - Jan 23

    Casa Bueras Boutique Hotel + Flight

    Downtown Santiago
    5 nights
    4.5 star property
    9.2/10 - Wonderful (568 reviews)
    "Great staff, location and breakfast. Enjoyed our stay here while visiting Ushuaia."
    Reviewed October 30, 2026
    Roundtrip • New York (NYC) - Santiago (SCL)
    JFK - SCL • Nonstop SCL - JFK • 1 stop
    $1,849
    $1,499
    per traveler
    found 1 day ago
    Casa Bueras Boutique Hotel
  • An outdoor patio area with stone arches, seating, and tables.
    Jan 13 - Jan 18

    Aubrey Hotel Boutique + Flight

    Bellavista
    4 nights
    4.0 star property
    9.4/10 - Exceptional (158 reviews)
    "Oriana was extremely helpful, engaged and pleasant. Very comfortable and excellent location."
    Reviewed November 1, 2026
    Roundtrip • Miami (MIA) - Santiago (SCL)
    MIA - SCL • Nonstop SCL - MIA • 1 stop
    $1,564
    $1,286
    per traveler
    found 0 hours ago
    Aubrey Hotel Boutique
  • An indoor swimming pool with a high ceiling, large windows, and multiple seating areas.
    Jan 6 - Jan 10

    Park Plaza Santiago + Flight

    Providencia
    3 nights
    4.0 star property
    8.4/10 - Very good (1,000 reviews)
    Roundtrip • Guatemala City (GUA) - Santiago (SCL)
    GUA - SCL • 1 stop SCL - GUA • 1 stop
    $1,050
    $890
    per traveler
    found 1 day ago
    Park Plaza Santiago
  • A balcony with a table and chairs, a potted plant, and a view of a building with multiple windows.
    Jan 11 - Jan 17

    Moderno depto. en Stgo. cerca del metro + Flight

    Downtown Santiago
    6 nights
    2.0 star property
    Roundtrip • San José (SJO) - Santiago (SCL)
    SJO - SCL • 1 stop SCL - SJO • 2 stops
    $1,080,589
    $924,934
    per traveler
    found 2 hours ago
    Moderno depto. en Stgo. cerca del metro

Discover the most popular places to visit in O'Higgins Region

Lapostolle Clos Apalta Winery

9.4/10 (21 reviews)
You can enjoy a tasting or tour at Lapostolle Clos Apalta Winery during your travels to Santa Cruz. While in this relaxing area, you can savor the wineries and restaurants.
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What to do in O'Higgins Region

Make Your Own Wine & Guided Vineyard Tour

Make Your Own Wine & Guided Vineyard Tour

$46
per adult
0% of travelers recommend
Make Your Own Wine & Guided Vineyard Tour
See all activities in O'Higgins Region

O'Higgins Region Hotel Deals

A traditional building with a tiled roof, a welcoming sign, and a large glass door.

Hotel Vendimia Parador

Hotel Vendimia Parador
3.0 star property
21.8 mi from O'Higgins Region
9.6 out of 10, Exceptional, (92 reviews)
"A bit outdated with lots of old furnishings. Beautiful place with friendly owners and beautiful gardens"
$116 nightly
The price is $116
Nov 30 - Dec 1
Hotel Vendimia Parador
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.
See all properties in O'Higgins Region
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.