San Jose Vacations & Trips from $1,061

Book a Hotel + Flight or Car together to unlock savings

Photo by Alejandro Ferrari

Your San Jose Vacation

Design the adventure you've always desired with a customized San Jose vacation package. A good starting point is San Jose de Mayo, where you can experience history, culture and many other highlights. Your trip to San Jose wouldn't be complete without checking out some of its best cities, starting with Juan Soler, Mal Abrigo and Ciudad del Plata. From the moment you book your San Jose vacation to the second you come back home, Expedia will be with you every step of the way.

Top destinations in San Jose

Ruta 11,uruguay
FlightsFlightsHotelsHotels

San Jose de Mayo

San Jose de Mayo

The Latest San Jose Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Regency Rambla Design Apart Hotel

Regency Rambla Design Apart Hotel

3.5 out of 5
Carrasco
Price was $1,237, price is now $1,061 per person
$1,061
per person
Feb 9 - Feb 13
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Montevideo (MVD)
16.8/10 Exceptional! (385 reviews)
Regency Park Hotel

Regency Park Hotel

4 out of 5
Price was $3,033, price is now $2,575 per person
$2,575
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Montevideo (MVD)
17.6/10 Exceptional! (228 reviews)
Tiene que continuar C la profesionalización del personal (son muy amables y respetuosos pero necesitan más entrenamiento El inmueble necesita una puesta al día (ej de noche no había agua caliente Pero la propiedad es hermosa ,

Reviewed on Aug 25, 2025

Sofitel Montevideo Casino Carrasco and Spa

Sofitel Montevideo Casino Carrasco and Spa

5 out of 5
Carrasco
Price was $1,487, price is now $1,263 per person
$1,263
per person
Feb 9 - Feb 13
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Montevideo (MVD)
18/10 Exceptional! (580 reviews)
The room looks a bit old, the curtains were detached on one side, and the electricity in my room stopped working one day so I had to change rooms.

Reviewed on Sep 22, 2025

HOTEL CENTENARIO

HOTEL CENTENARIO

3 out of 5
Price was $1,927, price is now $1,647 per person
$1,647
per person
Feb 9 - Feb 13
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Montevideo (MVD)
No reviews
Costanero Hotel Montevideo - MGallery Collection

Costanero Hotel Montevideo - MGallery Collection

5 out of 5
Pocitos
Price was $3,464, price is now $2,979 per person
$2,979
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Montevideo (MVD)
19.2/10 Exceptional! (311 reviews)
Really nice an modern hotel right next to the beach! I can recommend.

Reviewed on Sep 23, 2025

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

Best Places to Vacation in San Jose

1. Plan your dream getaway to San Jose de Mayo

San Jose de Mayo is a charming destination in Uruguay, perfect for a cultural vacation. The city boasts a unique atmosphere, with its rich history and vibrant local culture. Visitors can immerse themselves in the local theater scene, as the city is known for its theatrical productions. In addition to theater, there are plenty of activities for travelers to enjoy, such as destination activities and sightseeing tours. Whether exploring the historic landmarks or indulging in the local cuisine, San Jose de Mayo offers a delightful cultural experience for travelers seeking an authentic Uruguayan vacation.

  • The peak season is from February to April
  • The off-peak season is from October to December

Find the Best San Jose Vacation Packages

San Jose Essential Information

Language
Spanish
Currency
Uruguayan pesos
Local Welcome
¡Hola!
Local Goodbye
Adiós
Closest Airport
Carrasco Intl. Airport (MVD)
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a San Jose vacation package cost?
Perhaps less than you imagined — from only $1,061, in fact! By combining flights, hotels and car rentals into a customized vacation package, your trip to San Jose is only clicks away.
How do I get a cheap travel package to San Jose?
It's as simple as bundling. Flights, rental cars and hotels — combine whatever you need into a San Jose vacation package to save loads of cash. Score even more discounts when you add extras such as experiences or tours to your booking. But that's not the only impressive part. You have the freedom to tailor your trip your own way. We offer over 550 partner airlines and 1,000,000 hotels throughout the world, so that everyone has a chance to travel and live out those vacation dreams.
How far in advance should I book my San Jose vacation?
Search Expedia to compare international airfares as soon as possible. You can normally purchase a ticket up to 12 months before departure. If it's too early for your preferred air carrier, or you've left things to the last minute, don't worry. The lowest prices to San Jose sometimes appear within weeks of departure.
What does an Expedia San Jose travel package include?
Flights, hotels and rental cars, or any combination of them — it's your pick! Whether you're headed to San Jose with the family or traveling with your friends, there's a bundle to match your budget and style. Once you've made your booking, why not add on some tours and experiences?
What should I know before booking a San Jose travel package?
When you book your hotels, flights and car rentals together, you'll score incredible discounts. Whether you're planning a mountain getaway in a cabin or prefer to stay in a fancy hotel in the city, Expedia will help make it happen.
Can I choose my airline with a San Jose Expedia vacation package?
Yes, you can. We offer more than 550 airline partners across the globe, so go with the carrier that's a good fit for your travel preferences.
Does Expedia offer Book Now, Pay Later San Jose vacation packages?
Expedia works with online lender Affirm to help ease any financial stress related to your trip. This may be useful if your reason for travel has arisen suddenly. Book Now, Pay Later and spread the price of your flight and hotel package over multiple installments.
If I'm not able to travel, can I cancel my San Jose vacation package?
Don't worry if you're rethinking your San Jose vacation package — you can cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We totally understand your circumstances can change suddenly, so make your way to our Customer Service Portal if that occurs. When you're ready to make changes, we'll be here to help.

Discover the most popular places to visit in San Jose

Bartolome Maccio Theater

You can get tickets for a performance at Bartolome Maccio Theater during your stay in San Jose de Mayo. Take in the theater scene while you're in the area.

Bartolome Maccio Theater

What to do in San Jose

Visit to Winery Historic in Montevideo

Traditional and award-winning winery tour in Montevideo

$97
per adult
Traditional and award-winning winery tour in Montevideo
Montevideo Tailor-Made Experience — Private Tour with a Local

Montevideo Tailor-Made Experience — Private Tour with a Local

$252
per adult
100% of travellers recommend
Montevideo Tailor-Made Experience — Private Tour with a Local
Visit 2 wineries in a day

Visit 2 wineries in a day

$280
per adult
Visit 2 wineries in a day
See all activities in San Jose
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.