San Jose Vacations & Trips from $998
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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
San Jose de Mayo
Mal Abrigo
The Latest San Jose Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Regency Golf - Hotel Urbano
Punta Carretas
$998
per person
Dec 5 - Dec 12
just found
Roundtrip non-stop flight included
Miami (MIA) to Montevideo (MVD)
8.6/10 Excellent! (951 reviews)
Es una hotel limpio, personal agradable, desayuno variado, y una excelente ubicacion.
Las habitaciones son comodas y poseen heladerita, jarra electrica, microondas y vajilla por si uno quisiera cenar en la habitacion.
Yo no dudo en elegirlo cuando viajo a Montevideo.
Reviewed on Sep 19, 2026
Hotel Cottage
Carrasco
$1,265
per person
Dec 5 - Dec 12
just found
Roundtrip non-stop flight included
Miami (MIA) to Montevideo (MVD)
9/10 Wonderful! (267 reviews)
Everything excellent. The only improvement: add fresh squeezed orange juice to the breakfast. All world class hotels have it regardless of number of stars. All the rest awesome. Thanks!
Reviewed on Sep 30, 2026
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
Dazzler by Wyndham Montevideo
21 de Setiembre 2752 Montevideo
Fully refundableReserve now, pay when you stay
$122 nightly
$124 total
Oct 16 - Oct 17
Costanero Hotel Montevideo - MGallery Collection
Rambla Republica del Peru 1371 Montevideo
Fully refundableReserve now, pay when you stay
$180 nightly
$182 total
Oct 16 - Oct 17
9.6/10 Exceptional! (479 reviews)
"All good perfect"
Reviewed on Sep 28, 2026
Esplendor by Wyndham Montevideo Cervantes
Soriano 868 Montevideo
Fully refundableReserve now, pay when you stay
$89 nightly
$91 total
Oct 30 - Oct 31
8/10 Very Good! (951 reviews)
"Overall, I was disappointed with our stay. We moved to a different hotel after our original reservation was done. The hotel is close to La Ciudad de Viejo, which is nice. The breakfast was good, located on the roof, with a good view and a terrace. There was a working sauna. The things I didn't like ..."
Reviewed on Sep 25, 2026
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 San Jose vacation package cost?
Perhaps less than you imagined — from only $998, 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.
Stay near popular San Jose attractions
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.
Kartodromo Luis Pedro Serra
You can take time to visit Kartodromo Luis Pedro Serra during your travels to San Jose de Mayo. Take in the theater scene while you're in the area.
What to do in San Jose
Traditional and award-winning winery tour in Montevideo
$95
per adult
Tailor-made Montevideo: Private City Tour with a Local
$300
per adult
100% of travellers recommend
Private Wine Tours by Wine Explorers Uruguay
$205
per adult
100% of travellers recommend
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
