The Villages Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in The Villages
Price found within the past 48 hours. Click for updated prices.
Days Inn & Suites by Wyndham Mountain View
North Whisman
CA $656
per person
Oct 29 - Nov 1
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to San Jose (SJC)
7.2/10 Good! (1,006 reviews)
Weekend breakfast only open between 8-10 so those on business this property is not for you. No clock in the room, no wake up call ability and no courtesy cell phone chargers that might have been left behind by other guests. Ice machine was not working. Conditioner was not filled. No help from front desk and no copy of charges from room provided. I was told to contact 3rd party to check out which was odd. Positive was there is a pool and there is onsite free parking. I felt like I could been better off at a super 8.
Reviewed on Sep 21, 2026
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
Downtown San Jose
5 out of top 10 points of interest in this area
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 Market, and jump on the metro at Santa Clara Station or St James Station to see more of the city.
South San Jose
1 out of top 10 points of interest in this area
Southern region of San Jose, California, featuring a mix of businesses, green spaces, and parks. Explore trails like Coyote Creek and Guadalupe River, or visit parks such as Almaden Quicksilver County Park. Easily accessible via VTA stations and highways.
Willow Glen
Explore this historic downtown with diverse architectural styles, and upscale living. Enjoy shopping and dining in Downtown Willow Glen, and access nearby VTA light rail and Caltrain stations.
West San Jose
1 out of top 10 points of interest in this area
While visiting West San Jose, you might make a stop by sights like Winchester Mystery House and Santana Row Shopping Center.
North San Jose
If you're spending time in North San Jose, check out sights like Samsung Semiconductor Inc or Topgolf San Jose and hop on the metro to see more the city at Cisco Station or Baypointe Station.
The Villages Hotel Deals
Hyatt Place San Jose Airport
82 Karina Court, Airport San Jose CA
Fully refundableReserve now, pay when you stay
CA $189
CA $222 total
Oct 16 - Oct 17
includes taxes & fees
Sonesta Silicon Valley
1820 Barber Ln Milpitas CA
Fully refundableReserve now, pay when you stay
CA $145
CA $166 total
Oct 2 - Oct 3
includes taxes & fees
Wild Palms, a JdV by Hyatt Hotel
910 E Fremont Ave Sunnyvale CA
Fully refundableReserve now, pay when you stay
CA $153
CA $173 total
Sep 25 - Sep 26
includes taxes & fees
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 The Villages vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in The Villages from just CA $636. And the more you bundle, the more dollars you save. The vacation 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 vacation 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 vacation dreams.
Where should I stay in The Villages?
Most people who visit The Villages include both Winchester Mystery House and San Jose Convention Center 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 vacation?
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 cozy apartment in the city, Expedia can make it happen for less.
Can I choose my airline with a The Villages Expedia vacation 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 vacation package?
Certainly, and we're here to help. You may be able to amend or cancel your The Villages vacation 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.
Things to do
Niles History: An Audio Tour of the First Movie Capital
CA $14
per adult
San Francisco to Zion, Bryce, and Grand Canyon 4 Day Tour
CA $1,270
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.