O'Higgins Region Vacations & Trips from $724

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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 river delta, green hills, and a clear sky.

Navidad

Navidad
A vineyard with rows of grapevines.

Santa Cruz

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

Pichilemu

Pichilemu
A river winding through a valley with mountains in the background and a misty atmosphere.

San Vicente

San Vicente
A grassy field with cows grazing, surrounded by trees and mountains in the background.

Rancagua

Rancagua
A vineyard with rows of grapevines in autumn colors.

San Fernando

San Fernando

The Latest O'Higgins Region Vacation Packages

Price found within the past 48 hours. Click for updated prices.
LOFT Hotel by Sommelier Hoteles

LOFT Hotel by Sommelier Hoteles

Downtown Santiago
$724
per person
Dec 9 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
San José (SJO) to Santiago (SCL)
9/10 Wonderful! (275 reviews)
Matildas Hotel Boutique

Matildas Hotel Boutique

Downtown Santiago
$1,396
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip flight included
Panama City (PTY) to Santiago (SCL)
9.4/10 Exceptional! (294 reviews)
It was a quiet retreat in one of my favourite city:) lovely staff, and fantastic architecture!

Reviewed on Sep 26, 2026

Aubrey Hotel Boutique

Aubrey Hotel Boutique

Bellavista
$996
per person
Jan 13 - Jan 17
found 24 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Santiago (SCL)
9.4/10 Exceptional! (153 reviews)
Staff was really helpful especially Braulio if you have any questions he will answer them

Reviewed on Oct 16, 2026

45 by Director

45 by Director

Las Condes
$1,067
per person
Jan 1 - Jan 8
found 22 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Santiago (SCL)
9/10 Wonderful! (511 reviews)
Moderno depto. en Stgo. cerca del metro

Moderno depto. en Stgo. cerca del metro

Downtown Santiago
Save 100% on your flight
$617,040
per person
Jan 13 - Jan 17
found 24 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Santiago (SCL)
No reviews

Find the Best O'Higgins Region Vacation Packages

OHiggins Region Essential Information

Language
Spanish
Currency
Chilean pesos
Local Welcome
¡Hola!
Local Goodbye
Adiós
Closest Airport
Arturo Merino Benitez Airport (SCL)
Top Sights
Punta de Lobos Beach, Lobos Point and Pichilemu Beach

O'Higgins Region Hotel Deals

Vik Chile

Vik Chile

Valle de Millahue San Vicente O'Higgins
$734 nightly
$734 total
Oct 21 - Oct 22
9.2/10 Wonderful! (226 reviews)
"Sofia, Rodrigo, Matteo, Benjamin, Claudio, Chef Camillo, Javier and Fernanda were absolutely the highlight of our stay in terms of kind and genuine staff members. They truly exemplified hospitality. Food quality was excellent. Chef Camillo was truly world-class, amazing attention to detail and truly ..."

Reviewed on Sep 11, 2026

Vik Chile
Santa Cruz Plaza

Santa Cruz Plaza

Plaza De Armas 286 Santa Cruz O'Higgins
Fully refundableReserve now, pay when you stay
$119 nightly
$119 total
Nov 8 - Nov 9
8.8/10 Excellent! (376 reviews)
"Unfortunately our room faced the plaza and loud band until almost midnight! Also at 3 am we were awakened by loud tapping noise that lasted about 20 minutes"

Reviewed on Oct 18, 2026

Santa Cruz Plaza
Hotel Terrado Rancagua

Hotel Terrado Rancagua

290 Avenida Alberto Einstein Rancagua Racagua
Fully refundable
$80 nightly
$80 total
Oct 25 - Oct 26
9/10 Wonderful! (73 reviews)
"Room was clean and the staff was friendly. Very good breakfast buffet. The hotel was connected to the he mall, so plenty of shopping."

Reviewed on Oct 11, 2026

Hotel Terrado Rancagua
See all 291 properties in O'Higgins Region
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.

Stay near popular O'Higgins Region attractions

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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Colchagua Valley Wine Route

9.4/10 (32 reviews)
You can take time to visit Colchagua Valley Wine Route during your travels to Lolol. You can enjoy the wineries while in the area.
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Monticello Grand Casino and Convention Center

8.0/10 (1 review)
Why not try your luck with a visit to Monticello Grand Casino and Convention Center during your visit to Mostazal? Make some time to visit the casinos while you're in the area.
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Pichilemu Beach

9.0/10 (10 reviews)
Why not spend a carefree afternoon at Pichilemu Beach during your travels in Pichilemu? While you're in the area, wander around the natural setting.
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Lobos Point

9.4/10 (8 reviews)
Commune with nature and explore the great outdoors at Lobos Point during your travels in Pichilemu. Stroll along the seaside or discover the area's mountain views.
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Hacienda El Huique

7.0/10 (4 reviews)
You can spend time studying the exhibits at Hacienda El Huique in Palmilla. While in this relaxing area, you can enjoy the wineries.
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Millahue Valley

8.8/10 (12 reviews)
Commune with nature and explore the great outdoors at Millahue Valley during your travels in San Vicente.
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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
Make Your Own Wine & Guided Vineyard Tour
Private VIK winery tour + tasting from Santiago

Private VIK winery tour + tasting from Santiago

$365
per adult
Private VIK winery tour + tasting from Santiago
Private Wine Tour Colchagua Valley

Private Wine Journey Through Colchagua Valley

$450
per adult
Private Wine Journey Through Colchagua Valley
See all activities in O'Higgins Region
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