The Villages Vacation Packages

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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

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Top Holiday Package Deals in The Villages

Price found within the past 48 hours. Click for updated prices.
ROYAL INN

ROYAL INN

2 out of 5
Price was CA $1,125, price is now CA $954 per person
CA $954
per person
Jul 25 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Jose (SJC)
7.2/10 Good! (144 reviews)
Esta muy limpia y muy amplia

Reviewed on May 7, 2026

Shashi Hotel Mountain View Palo Alto

Shashi Hotel Mountain View Palo Alto

5 out of 5
Price was CA $3,602, price is now CA $2,795 per person
CA $2,795
per person
Jul 24 - Jul 31
found 16 hours ago
Roundtrip flight included
Montreal (YMQ) to San Jose (SJC)
9.4/10 Exceptional! (1,403 reviews)
Love the welcome glass of champagne! Easy walking to CHM and the theater and Zareens! Beautiful and swanky hotel.

Reviewed on Jun 19, 2026

@ Marbella Lane - SJ Designer Home 12-min to Levi's

@ Marbella Lane - SJ Designer Home 12-min to Levi's

3 out of 5
Price was CA $2,911, price is now CA $2,290 per person
CA $2,290
per person
Aug 28 - Aug 31
found 15 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to San Jose (SJC)
No reviews
Sonesta Silicon Valley

Sonesta Silicon Valley

4 out of 5
Price was CA $2,234, price is now CA $1,858 per person
CA $1,858
per person
Jul 24 - Jul 31
found 16 hours ago
Roundtrip flight included
Montreal (YMQ) to San Jose (SJC)
9.2/10 Wonderful! (2,000 reviews)
so far so gorgeous! i was upgraded to a suite due to being an expedia member. this place is so professional, so beautiful. clean, sleek, wow. the ladies at the front desk were incredibly informative and helpful without even needing to ask (so rare, honestly) and as was the bartender maria! you get a free drink for less than 12$, but u do need to pay a 75$ pet fee and an overnight parking fee. still! i loved this place! im definitely going to seek out more sonesta properties next time im out and about! even the keycards had astrological fun facts and on the bed was a cute bedtime journaling prompt.

Reviewed on Jun 21, 2026

The Ameswell Hotel

The Ameswell Hotel

4.5 out of 5
Price was CA $2,859, price is now CA $2,391 per person
CA $2,391
per person
Jul 24 - Jul 31
found 16 hours ago
Roundtrip flight included
Montreal (YMQ) to San Jose (SJC)
9.6/10 Exceptional! (1,311 reviews)
The pool was well maintained and a great hang out spot. It is worth taking a trip to the bar and having a margarita by the pool. The rooms were also super clean and comfortable. Every single staff member I encountered was kind and helpful.

Reviewed on Jun 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

Downtown San Jose

4 out of top 10 points of interest in this area
4.5/5(31 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

The Villages Hotel Deals

Wild Palms, a JdV by Hyatt Hotel

Wild Palms, a JdV by Hyatt Hotel

3 out of 5
910 E Fremont Ave Sunnyvale CA
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Jul 3 to Jul 4
CA $135
CA $152 total
Jul 3 - Jul 4
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"TV was not working."

Reviewed on Jun 22, 2026

Wild Palms, a JdV by Hyatt Hotel
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 $131 per night from Jul 3 to Jul 4
CA $131
CA $148 total
Jul 3 - Jul 4
includes taxes & fees
9/10 Wonderful! (2,831 reviews)
"A great place to stay."

Reviewed on Jun 22, 2026

Maple Tree Inn
Holiday Inn San Jose - Silicon Valley by IHG

Holiday Inn San Jose - Silicon Valley by IHG

3 out of 5
1350 N 1st Street San Jose CA
Fully refundable
The price is CA $174 per night from Jul 3 to Jul 4
CA $174
CA $200 total
Jul 3 - Jul 4
includes taxes & fees
8.2/10 Very Good! (1,123 reviews)
"The room was very strong cigar odor we had to open the window to vent the air also they charged for parking and that wasn’t clarify in the reservation too expensive $440 for 2 nights never again"

Reviewed on Jun 22, 2026

Holiday Inn San Jose - Silicon Valley by IHG
See all 1,569 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 $954. 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

You can browse for souvenirs with a trip to Santana Row Shopping Center, a favorite shopping spot in San Jose. 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 $42
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.