San Jose Vacations & Trips from $1,095

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 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

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

Uruguay, Streets of Colonia Del Sacramento in historic center (Barrio Historico)
FlightsFlightsHotelsHotels

San Jose de Mayo

San Jose de Mayo
Colonia del Sacramento Lighthouse, Uruguay
FlightsFlightsHotelsHotels

Mal Abrigo

Mal Abrigo

The Latest San Jose Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Regency Golf - Hotel Urbano

Regency Golf - Hotel Urbano

4 out of 5
Punta Carretas
Price was $1,239, price is now $1,095 per person
$1,095
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Montevideo (MVD)
8.6/10 Excellent! (908 reviews)
The hotel was really nice, wonderful staff, clean and comfortable room. Breakfast was good. I will come back.

Reviewed on Mar 26, 2026

Regency Park Hotel

Regency Park Hotel

4 out of 5
Price was $1,319, price is now $1,131 per person
$1,131
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Montevideo (MVD)
8.8/10 Excellent! (238 reviews)
Clean rooms, friendly staff, great location. Will stay again.

Reviewed on Mar 4, 2026

Regency Way Montevideo Hotel

Regency Way Montevideo Hotel

3.5 out of 5
Pocitos
Price was $1,249, price is now $1,100 per person
$1,100
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Montevideo (MVD)
8.8/10 Excellent! (1,001 reviews)
Bathroom broken and had bad odors, floor dirty I was so disappointed.

Reviewed on Apr 9, 2026

Charco Hotel

Charco Hotel

3.5 out of 5
Barrio Histórico
Price was $1,475, price is now $1,304 per person
$1,304
per person
May 21 - May 24
found 1 hour ago
Roundtrip non-stop flight included
Chicago (ORD) to Montevideo (MVD)
9.6/10 Exceptional! (268 reviews)
Very nice boutique hotel. 9 rooms. Very nice dining area with ocean view and good local wines. Near the ferry terminal and easy walking distance to the old town. Clean and good AC.

Reviewed on Feb 23, 2026

Own Montevideo

Own Montevideo

4 out of 5
Punta Carretas
Price was $1,261, price is now $1,121 per person
$1,121
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Montevideo (MVD)
8.8/10 Excellent! (566 reviews)
Great location , walking distance to boardwalk , shopping center & restaurants. Great staff & decent breakfast.

Reviewed on Mar 3, 2026

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)

San Jose Hotel Deals

Hotel Montevideo - Leading Hotels of the World

Hotel Montevideo - Leading Hotels of the World

5 out of 5
2905 José Benito Lamas Montevideo
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $187 total per night from Apr 13 to Apr 14
$187 total
Apr 13 - Apr 14
9.6/10 Exceptional! (497 reviews)
A really nice vintage hotel in the center of Montevideo!

Reviewed on Apr 10, 2026

Hotel Montevideo - Leading Hotels of the World
Dazzler by Wyndham Montevideo

Dazzler by Wyndham Montevideo

3.5 out of 5
21 de Setiembre 2752 Montevideo
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $110 total per night from Apr 13 to Apr 14
$110 total
Apr 13 - Apr 14
8.2/10 Very Good! (1,007 reviews)
The breakfast was very poor , there is no. variation , always the same , no god ham , always the same cakes

Reviewed on Mar 27, 2026

Dazzler by Wyndham Montevideo
Palladium Business Hotel

Palladium Business Hotel

3.5 out of 5
Tomás de Tezanos 1146 Montevideo
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $67 total per night from May 3 to May 4
$67 total
May 3 - May 4
8.4/10 Very Good! (625 reviews)
Every thing was fantastic

Reviewed on Mar 7, 2026

Palladium Business Hotel
See all 261 properties in San Jose
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.
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 $1,095, 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

Montevideo Tailor-Made Experience — Private Tour with a Local

Tailor-made Montevideo: Private City Tour with a Local

$210
per adult
100% of travellers recommend
Tailor-made Montevideo: Private City Tour with a Local
Traditional and award-winning winery tour in Montevideo

Traditional and award-winning winery tour in Montevideo

$108
per adult
Traditional and award-winning winery tour in Montevideo
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.