The Villages Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    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

Top Holiday Package Deals in The Villages

Price found within the past 48 hours. Click for updated prices.
Aloft Cupertino

Aloft Cupertino

3 out of 5
Price was CA $1,120, price is now CA $914 per person
CA $914
per person
Jul 23 - Jul 27
found 2 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Jose (SJC)
8.8/10 Excellent! (1,009 reviews)
This place was exceptional and surprisingly because of the low price. Definitely stay here again

Reviewed on May 5, 2026

Shashi Hotel Mountain View Palo Alto

Shashi Hotel Mountain View Palo Alto

5 out of 5
Price was CA $2,568, price is now CA $1,844 per person
CA $1,844
per person
Jun 11 - Jun 14
found 18 hours ago
Roundtrip flight included
Calgary (YYC) to San Jose (SJC)
9.4/10 Exceptional! (1,362 reviews)
Clean room since cleaned every night we were there

Reviewed on May 4, 2026

Avatar Hotel Santa Clara, Tapestry Collection by Hilton

Avatar Hotel Santa Clara, Tapestry Collection by Hilton

3.5 out of 5
Price was CA $1,450, price is now CA $1,149 per person
CA $1,149
per person
Jul 23 - Jul 27
found 2 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Jose (SJC)
8.8/10 Excellent! (279 reviews)
Excelente servicio y precio el personal muy amable

Reviewed on Apr 19, 2026

Chase Suite Hotel Newark-Fremont

Chase Suite Hotel Newark-Fremont

3.5 out of 5
Price was CA $1,183, price is now CA $1,020 per person
CA $1,020
per person
Jul 23 - Jul 27
found 2 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Jose (SJC)
8.6/10 Excellent! (1,004 reviews)
The breakfast was delicious, offering something new each day for a hot breakfast. My only complaint was the mattress for the pullout bed was terrible, old and very worn. We were unable to use the pullout bed which we were planning on using! Overall it was a nice place to stay!

Reviewed on May 5, 2026

The Ameswell Hotel

The Ameswell Hotel

4.5 out of 5
Price was CA $1,352, price is now CA $1,199 per person
CA $1,199
per person
Jul 23 - Jul 27
found 2 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Jose (SJC)
9.6/10 Exceptional! (1,251 reviews)
I always love staying here Staff is amazing

Reviewed on May 4, 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

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 San Pedro Square and San Jose Museum of Art, 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

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 CA $138 per night from May 15 to May 16
CA $138
CA $155 total
May 15 - May 16
includes taxes & fees
9/10 Wonderful! (2,728 reviews)
This is my go-to place every time I need to come down to Sunnyvale. Always welcoming, never a problem.

Reviewed on May 5, 2026

Maple Tree Inn
Hyatt Place San Jose Airport

Hyatt Place San Jose Airport

3 out of 5
82 Karina Court, Airport San Jose CA
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from May 16 to May 17
CA $179
CA $206 total
May 16 - May 17
includes taxes & fees
9/10 Wonderful! (1,542 reviews)
Very bright and friendly accommodations. Staff was helpful. Breakfast was great. Highly recommend.

Reviewed on May 5, 2026

Hyatt Place San Jose Airport
Sonesta San Jose - Milpitas

Sonesta San Jose - Milpitas

3.5 out of 5
777 Bellew Dr Milpitas CA
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from May 23 to May 24
CA $143
CA $163 total
May 23 - May 24
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
Stay was pretty good, I was skeptical at first looking at the yelp reviews but no complaints about our stay. Would definitely stay here again plus they have really hot water which is a plus

Reviewed on May 5, 2026

Sonesta San Jose - Milpitas
See all 1,597 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $914. 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.

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 enjoy retail therapy 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

Things to do

LEGOLAND Discovery Center Bay Area

LEGOLAND Discovery Center Bay Area

CA $39
per adult
LEGOLAND Discovery Center Bay Area
Picture 2 for Activity San Jose: Valley Ghosts Haunted Walking Tour

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

CA $44
per adult
San Jose Ghost Tour: The Scythe, Sacrifice, & Silhouette
Special Ops: Mysterious Market

The Escape Game San Jose: Epic 60-Minute Adventure at Valley Fair

CA $65
per adult
The Escape Game San Jose: Epic 60-Minute Adventure at Valley Fair
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.