The Villages Holidays

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Your The Villages Holiday

Experience the best that The Villages has to offer with a The Villages holiday package. From its golfing to everything else that makes it so fascinating, this neighbourhood will delight you from beginning to end. Plan enough time on your itinerary to see renowned nearby sights like Montgomery Hill during your trip to The Villages. Don't just wish for it — make it happen! Secure your perfect The Villages holiday with Expedia and get to where you're going your way.

Our guide on where to stay in The Villages

Find the best The Villages areas and neighborhoods for the activities you enjoy most. Learn more about The Villages
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Downtown San Jose

4 out of top 10 points of interest in this area
4.5/5(5 area reviews)

Known for its fascinating museums and great live music, there's plenty to explore in Downtown San Jose. You can visit top attractions like SAP Center at San Jose and San Pedro Square, and jump on the metro at Santa Clara Station or St James Station to see more of the city.

Find hotels in Downtown San Jose

Our pick of the best The Villages Hotel Deals

Maple Tree Inn

Maple Tree Inn

3 out of 5
711 E El Camino Real, Sunnyvale, CA
Fully refundableReserve now, pay when you stay
The price is AU$169 per night from 4 Oct to 5 Oct
AU$169
4 Oct - 5 Oct
includes taxes & fees
9/10 Wonderful! (2,285 reviews)
"It was a nice motel"

Reviewed on 24 Sept 2025

Maple Tree Inn
Uptown Oasis San Jose Airport

Uptown Oasis San Jose Airport

3 out of 5
1355 N 4th Street, San Jose, CA
Fully refundableReserve now, pay when you stay
The price is AU$141 per night from 28 Sept to 29 Sept
AU$141
28 Sept - 29 Sept
includes taxes & fees
7.8/10 Good! (462 reviews)
"It wad cool. There was a spider. No big deal."

Reviewed on 24 Sept 2025

Uptown Oasis San Jose Airport
Sonesta Silicon Valley

Sonesta Silicon Valley

4 out of 5
1820 Barber Ln, Milpitas, CA
Fully refundable
The price is AU$195 per night from 10 Oct to 11 Oct
AU$195
10 Oct - 11 Oct
includes taxes & fees
9/10 Wonderful! (1,634 reviews)
"Clean big rooms quiet"

Reviewed on 23 Sept 2025

Sonesta Silicon Valley
See all 1,719 properties in The Villages
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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a The Villages holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in The Villages from just . And the more you bundle, the more dollars you save. The holiday of your dreams has never been so affordable.
How do I get a cheap travel package to The Villages?
One word: bundle. Flights, hotels and rental cars — combine whatever you need into a The Villages holiday package and save. Score even more discounts when you add extras such as tours or experiences to your booking. But that's not the only good part. You have the freedom to customize your trip your own way. We offer over 550 air carriers and 1 000 000 hotel options across the world, so that everyone has an opportunity to travel and live out those holiday dreams.
Where should I stay in The Villages?
Most people who visit The Villages include both Winchester Mystery House and San Jose Convention Centre on their bucket lists. Why not select a hotel close to one of these popular attractions?
How far in advance should I book my The Villages holiday?
While not all air carriers release ticket prices early, you can normally start comparing international fares on Expedia up to a year in advance. This is when you'll nab some fantastic bargains. If you've left things to the last minute, you might still get lucky. Sometimes the lowest prices become available only weeks prior to departure.
What does an Expedia The Villages travel package include?
Flights, rental cars and hotels — you'll find them all here. With Expedia, you can create your The Villages package just how you like it. All you have to do is work out what you need. Once you've made your booking, you can add on extras like activities and tours. The more you bundle, the greater the savings!
What should I know before booking a The Villages travel package?
When you book your hotels, flights and car rentals together, you'll walk away with awesome discounts. Whether you're planning a rural escape in a cottage or would rather stay in a cosy apartment in the city, Expedia can make it happen for less.
Can I choose my airline with a The Villages Expedia holiday package?
Yes, and with more than 550 airlines to select from globally, you've got lots of choice. Have a look through the available options and see which airline best fits your budget and needs.
If I'm not able to travel, can I cancel my The Villages holiday package?
Certainly, and we're here to help. You may be able to amend or cancel your The Villages holiday package for free within 24 hours of booking. But you may incur a fee from your airline, hotel or car rental company if you booked more than 24 hours ago. If your travel plans suddenly change, take a look at our Customer Service Portal for more information.

Discover the most popular places to visit in The Villages

Santana Row Shopping Center

Santana Row Shopping Center

During your trip to San Jose, you can find the perfect gifts to bring home at Santana Row Shopping Center. Attend a sporting event or discover the mountain views in this family-friendly area.

Santana Row Shopping Center
Winchester Mystery House

Winchester Mystery House

Wonder about the alleged hauntings and other mysteries as you chart the life of a gun magnate’s widow in this unfinished manor.

Winchester Mystery House
Raging Waters

Raging Waters

Bring your family to Raging Waters and enjoy some excitement at this theme park in San Jose. Discover the top-notch restaurants and great live music in this family-friendly area.

Raging Waters

Activities

Picture 2 for Activity San Jose: Valley Ghosts Haunted Walking Tour

San Jose Ghost Tour: The Scythe, Sacrifice, & Silhouette

AU$48
per adult
San Jose Ghost Tour: The Scythe, Sacrifice, & Silhouette
San Jose: One day Yosemite and Giant Sequoia Tour

San Jose: One day Yosemite and Giant Sequoias Tour

AU$437
per adult
92% of travellers recommend
San Jose: One day Yosemite and Giant Sequoias Tour
Turkish Mosaic Lamp Making Workshop

Turkish Mosaic Lamp Making Workshop

AU$144
per adult
Turkish Mosaic Lamp Making Workshop
See all activities in San Jose
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.