Oakland Estates Vacations from $459

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Your Oakland Estates Vacation

Our Oakland Estates vacation packages are a speedy and practical way to plan and book your next retreat. Uncover the true character of this unique neighborhood without the burden of planning it all yourself. When it's time to get out and explore, you'll find loads of popular attractions nearby including University of Texas Health and Science Center at San Antonio, Huebner Oaks and Oak Hills Country Club. Tick off one or all during your trip to Oakland Estates. No matter your travel goals or budget, booking your dream Oakland Estates vacation is a cinch with Expedia.

The Latest Oakland Estates Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The St. Anthony, A Luxury Collection Hotel, San Antonio

The St. Anthony, A Luxury Collection Hotel, San Antonio

4.5 out of 5
Downtown San Antonio
Price was $608, price is now $459 per person
$459
per person
May 19 - May 21
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to San Antonio (SAT)
8.8/10 Excellent! (1,004 reviews)
It was a beautiful hotel, easy check in, ans centrally located.

Reviewed on Mar 15, 2026

Signia by Hilton La Cantera Resort & Spa

Signia by Hilton La Cantera Resort & Spa

4 out of 5
La Cantera District
Save 100% on your flight
Price was $1,033, price is now $672 per person
$672
per person
May 8 - May 12
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to San Antonio (SAT)
9/10 Wonderful! (1,031 reviews)
Clean room | Amazing staff |

Reviewed on Mar 19, 2026

Hyatt Vacation Club at Wild Oak Ranch, San Antonio

Hyatt Vacation Club at Wild Oak Ranch, San Antonio

3.5 out of 5
Far West Side
Save 100% on your flight
Price was $990, price is now $710 per person
$710
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to San Antonio (SAT)
9/10 Wonderful! (1,504 reviews)
great pools perfect place for families

Reviewed on Mar 25, 2026

The Continental, powered by Placemakr - Downtown - Market Square

The Continental, powered by Placemakr - Downtown - Market Square

3.5 out of 5
Downtown San Antonio
Price was $724, price is now $542 per person
$542
per person
May 13 - May 17
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to San Antonio (SAT)
9.6/10 Exceptional! (84 reviews)
Parking is a bit frustrating, but cheaper than other places

Reviewed on Mar 27, 2026

Tx Home Group- San Antonio

Tx Home Group- San Antonio

2 out of 5
Midtown
Price was $1,296, price is now $1,000 per person
$1,000
per person
May 20 - May 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Antonio (SAT)
10/10 Exceptional! (6 reviews)
Nightclub area; noisy at night at times; no close shopping; highway driving across town. Initial instructions were confusing but host was great. Pool and gym access; good for active people.

Reviewed on Mar 14, 2026

Where to stay in Oakland Estates

Find the best Oakland Estates areas and neighborhoods for the activities you enjoy most. Learn more about Oakland Estates
Downtown San Antonio

Downtown San Antonio

4 out of top 10 points of interest in this area
4/5(9,632 area reviews)

Explore the heart of San Antonio with top attractions like the Alamo and River Walk, or enjoy kayaking and bicycling to the World Heritage Missions. Discover historic sites, theaters, and shopping at Rivercenter, all easily accessible by public transit.

Find hotels in Downtown San Antonio

Oakland Estates Hotel Deals

Riverwalk Plaza

Riverwalk Plaza

4 out of 5
100 Villita Street San Antonio TX
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $117 total per night from Apr 5 to Apr 6
$117 total
Apr 5 - Apr 6
Total with taxes and fees
8/10 Very Good! (6,405 reviews)
.

Reviewed on Mar 27, 2026

Riverwalk Plaza
Hotel Valencia Riverwalk

Hotel Valencia Riverwalk

4.5 out of 5
150 E Houston St San Antonio TX
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $197 total per night from Apr 1 to Apr 2
$197 total
Apr 1 - Apr 2
Total with taxes and fees
9.4/10 Exceptional! (2,581 reviews)
Lovely rooms, attentive staff, great location. Thoroughly enjoyed our three night stay!

Reviewed on Mar 26, 2026

Hotel Valencia Riverwalk
Hyatt Vacation Club at Wild Oak Ranch, San Antonio

Hyatt Vacation Club at Wild Oak Ranch, San Antonio

3.5 out of 5
9700 West Military Drive San Antonio TX
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $147 total per night from Apr 13 to Apr 14
$147 total
Apr 13 - Apr 14
Total with taxes and fees
9/10 Wonderful! (1,526 reviews)
great pools perfect place for families

Reviewed on Mar 25, 2026

Hyatt Vacation Club at Wild Oak Ranch, San Antonio
See all 4,743 properties in Oakland Estates
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 Oakland Estates

River Walk

River Walk

4.5/5(7,392 reviews)

When you visit San Antonio, this neighborhood will keep you entertained for days, from morning coffee to an evening theater performance.

River Walk
An Air Force Security Forces K-9 handler, and his military working dog, track an armed assailant into a trailer home and prepare to take the perpetrator down by force.

Lackland Air Force Base

4.5/5(1,269 reviews)

Lackland Air Force Base is just one of the places to see in San Antonio, so why not enjoy the other things to explore during your travels? Discover the entertainment venues and shops in this family-friendly area.

Lackland Air Force Base
Roller Coaster

Six Flags Fiesta Texas

4.5/5(981 reviews)

Enjoy the rides and games at Six Flags Fiesta Texas and see why this is a favorite theme park in San Antonio. Experience the entertainment choices and lively festivals in this family-friendly area.

Six Flags Fiesta Texas

Things to do

Picture 1 for Activity San Antonio: Twisted Trails Zip Rails, Ropes & Climbing Wall

San Antonio: Twisted Trails Zip Rails, Ropes & Climbing Wall

$42
per adult
San Antonio: Twisted Trails Zip Rails, Ropes & Climbing Wall
San Antonio: Fredericksburg Wineries Day Trip with Tastings

San Antonio: Fredericksburg Wineries Day Trip with Tastings

$179
per adult
100% of travellers recommend
San Antonio: Fredericksburg Wineries Day Trip with Tastings
San Antonio: Discovery Tour at Natural Bridge Caverns

San Antonio: Discovery Tour at Natural Bridge Caverns

$38
per adult
98% of travellers recommend
San Antonio: Discovery Tour at Natural Bridge Caverns
See all activities in San Antonio
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.