Oakland Estates Vacations from $612

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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 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 $798, price is now $612 per person
$612
per person
Jun 4 - Jun 8
found 22 hours ago
Roundtrip non-stop flight included
New York (NYC) to San Antonio (SAT)
9.6/10 Exceptional! (84 reviews)
nice locations pretty quiet

Reviewed on Mar 14, 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 $1,289, price is now $919 per person
$919
per person
May 7 - May 11
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Antonio (SAT)
9/10 Wonderful! (1,031 reviews)
Clean room | Amazing staff |

Reviewed on Mar 19, 2026

Club Wyndham La Cascada

Club Wyndham La Cascada

4 out of 5
Downtown San Antonio
Save 100% on your flight
Price was $936, price is now $705 per person
$705
per person
Apr 30 - May 4
just found
Roundtrip non-stop flight included
Philadelphia (PHL) to San Antonio (SAT)
8.4/10 Very Good! (181 reviews)
My family and I had a lovely weekend. The view from my balcony was so beautiful and very peaceful. Overall wonderful stay!

Reviewed on Aug 22, 2025

Hyatt Regency Hill Country Resort and Villas

Hyatt Regency Hill Country Resort and Villas

4 out of 5
Far West Side
Price was $1,405, price is now $1,140 per person
$1,140
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to San Antonio (SAT)
8.8/10 Excellent! (1,003 reviews)
It was a beautiful place, cant wait to go back

Reviewed on Mar 21, 2026

Club Wyndham Riverside Suites

Club Wyndham Riverside Suites

3.5 out of 5
Downtown San Antonio
Price was $1,048, price is now $865 per person
$865
per person
Apr 27 - May 1
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to San Antonio (SAT)
7.6/10 Good! (93 reviews)
Staff was very friendly and easy check in!

Reviewed on Jan 5, 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 - Riverwalk which includes heritage architecture, boating and a river or creek

Downtown San Antonio

4 out of top 10 points of interest in this area
4/5(9,564 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
$100 nightly
The price is $118 total per night from Apr 5 to Apr 6
$118 total
Apr 5 - Apr 6
Total with taxes and fees
8/10 Very Good! (6,418 reviews)
Very nice hotel. And very convenient for walking on the Riverwalk, The Alamo or other nearby attractions.

Reviewed on Mar 24, 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
$170 nightly
The price is $200 total per night from Apr 1 to Apr 2
$200 total
Apr 1 - Apr 2
Total with taxes and fees
9.4/10 Exceptional! (2,571 reviews)
Nice location and nice rooms. The lobby smells amazing so I was hopeful that the lotion and shampoo/conditioner would as well. Not so much. The lotion smelled old so that was disappointing. Otherwise, we had a good stay and would recommend.

Reviewed on Mar 24, 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
$134 nightly
The price is $159 total per night from Apr 13 to Apr 14
$159 total
Apr 13 - Apr 14
Total with taxes and fees
9/10 Wonderful! (1,522 reviews)
Very spacious. Great for the family.

Reviewed on Mar 23, 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 featuring night scenes and a river or creek

River Walk

4.5/5(7,291 reviews)

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

River Walk
Air Force Security Forces K-9 handler, and her military working dog, seek out drugs inside a training house.

Lackland Air Force Base

4.5/5(1,257 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(972 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.