The Villages Vacations from $222

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Your The Villages Vacation

Experience the best that The Villages has to offer with a The Villages vacation package. From its golfing to everything else that makes it so fascinating, this neighborhood 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 vacation with Expedia and get to where you're going your way.

The Latest The Villages Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place San Jose Airport

Hyatt Place San Jose Airport

3 out of 5
North San Jose
Save 100% on your flight
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Jose (SJC)
8.8/10 Excellent! (1,403 reviews)
The staff at the front desk was extremely helpful.

Reviewed on Jul 11, 2025

Aqua Breeze Inn

Aqua Breeze Inn

2.5 out of 5
Westside Santa Cruz
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Jose (SJC)
8/10 Very Good! (1,008 reviews)
Pros: good price, nice staff, separate bedroom, very close to the boardwalk and beach, free parking/availability, fridge, microwave, allow pets, good plumbing/hot water. Cons: paper thin walls, uncomfortable beds (can feel the springs), bad WiFi, cheap towels & bedding. It’s definitely a 2-3 star motel but if you’re traveling on a small budget, you’ll appreciate it.

Reviewed on Jul 9, 2025

Shashi Hotel Mountain View Palo Alto

Shashi Hotel Mountain View Palo Alto

5 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Jose (SJC)
9.4/10 Exceptional! (1,010 reviews)
The staff was so accommodating. It was clean and very relaxing! Loved the spa!

Reviewed on Jul 6, 2025

Chaminade Resort & Spa

Chaminade Resort & Spa

4 out of 5
Save 100% on your flight
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Jose (SJC)
8/10 Very Good! (1,003 reviews)
The location was great. The service was hit and miss. The pool was freezing though supposed to be heated and the Hot Tub did not function properly.

Reviewed on Jul 10, 2025

Howard Johnson by Wyndham Santa Cruz Beach Boardwalk

Howard Johnson by Wyndham Santa Cruz Beach Boardwalk

2 out of 5
Westside Santa Cruz
Save 100% on your flight
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Jose (SJC)
7/10 Good! (1,000 reviews)
Place was older but seem clean

Reviewed on Jul 5, 2025

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 featuring heritage architecture

Downtown San Jose

3 out of top 10 points of interest in this area
4/5(936 area reviews)

This city on San Francisco Bay is not only a technology center, but also filled with cultural and historic attractions.

Find hotels in Downtown San Jose

The Villages Hotel Deals

Hyatt Centric Santa Clara Silicon Valley
Hyatt Centric Santa Clara Silicon Valley
3.5 out of 5
3100 Lakeside Dr, Santa Clara, CA
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $159 total per night from Jul 25 to Jul 26
$159 total
Jul 25 - Jul 26
Total includes taxes and fees
8.8/10 Excellent! (1,005 reviews)
Quite noisy
"Newer looking hotel in an industrial area next an abandoned looking construction site. Quite noisy inside. Could hear people talking in adjecent rooms and hallway. We stayed in the top floor and the AC units on the roof sounded like jet engines taking off ...all night. We stayed in a 1 bedroom suit. ..."

Reviewed on Jul 8, 2025

Hyatt Centric Santa Clara Silicon Valley
Maple Tree Inn
Maple Tree Inn
3 out of 5
711 E El Camino Real, Sunnyvale, CA
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $123 total per night from Jul 18 to Jul 19
$123 total
Jul 18 - Jul 19
Total includes taxes and fees
8.8/10 Excellent! (2,078 reviews)
"Great pool. Good breakfast. Great staff."

Reviewed on Jul 9, 2025

Maple Tree Inn
Sonesta Silicon Valley
Sonesta Silicon Valley
4 out of 5
1820 Barber Ln, Milpitas, CA
Fully refundable
$110 nightly
The price is $125 total per night from Jul 18 to Jul 19
$125 total
Jul 18 - Jul 19
Total includes taxes and fees
9/10 Wonderful! (1,509 reviews)
"Clean"

Reviewed on Jul 9, 2025

Sonesta Silicon Valley
See all 1,702 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

Kid Friendly Vacations

Kid Friendly Vacations

Discover the most popular places to visit in The Villages

This is a great place across from the mall where you could eat at a diverse set of restaurants!

Santana Row Shopping Center

4.5/5(119 reviews)

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

4.5/5(569 reviews)

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 showing a waterpark and swimming as well as a large group of people

Raging Waters

5/5(1 review)

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

San Jose: One day Yosemite and Giant Sequoia Tour

San Jose: One day Yosemite and Giant Sequoias Tour

$289
per adult
92% of travellers recommend
San Jose: One day Yosemite and Giant Sequoias Tour
Picture 2 for Activity San Jose: Valley Ghosts Haunted Walking Tour

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

$24
per adult
San Jose Ghost Tour: The Scythe, Sacrifice, & Silhouette
San Jose Earthquakes Football Game at PayPal Park

San Jose Earthquakes Football Game at PayPal Park

$15
per adult
San Jose Earthquakes Football Game at PayPal Park
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.