Oakland Estates Vacations from $251

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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.
Holiday Inn Express & Suites San Antonio Medical-Six Flags by IHG

Holiday Inn Express & Suites San Antonio Medical-Six Flags by IHG

2.5 out of 5
Northwest Side
Price was $320, price is now $251 per person
$251
per person
May 8 - May 10
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
7.8/10 Good! (1,076 reviews)
Subject: Concern About How My Issue Was Handled Hello, I would like to share something that happened during my recent visit. I had been waiting patiently for an issue to be resolved with the elevator along with another customer. While we were waiting for help, Paul spoke to me in a way that felt embarrassing, especially because it happened in front of the other customer. I want to say that Liz later stepped in and helped resolve the issue after the fact, and I appreciate her assistance. She handled the situation kindly and helped bring it to a resolution. My concern is mainly about how I was addressed earlier in front of others. It was uncomfortable and discouraging. I simply hope that in the future situations like this can be handled with a little more understanding and privacy. Thank you for taking the time to read this and for considering my concern. Respectfully,

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 $566, price is now $398 per person
$398
per person
May 8 - May 10
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9/10 Wonderful! (1,031 reviews)
Overall good stay. Would definitely stay there again

Reviewed on Mar 9, 2026

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 $1,053, price is now $784 per person
$784
per person
Apr 28 - May 2
found 17 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

Hotel Contessa

Hotel Contessa

4 out of 5
Downtown San Antonio
Price was $687, price is now $537 per person
$537
per person
May 23 - May 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to San Antonio (SAT)
9/10 Wonderful! (3,481 reviews)
Great remodel! Great hospitality!

Reviewed on Mar 14, 2026

Hyatt Regency Hill Country Resort and Villas

Hyatt Regency Hill Country Resort and Villas

4 out of 5
Far West Side
Save 100% on your flight
Price was $1,352, price is now $1,073 per person
$1,073
per person
May 6 - May 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to San Antonio (SAT)
8.8/10 Excellent! (1,001 reviews)
Felt like a vacation. It was perfect

Reviewed on Feb 11, 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(9,525 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
$119 nightly
The price is $141 total per night from Apr 5 to Apr 6
$141 total
Apr 5 - Apr 6
Total with taxes and fees
8/10 Very Good! (6,392 reviews)
Hotel was clean, staff was friendly and location was steps to the Riverwalk. Would stay again!

Reviewed on Mar 15, 2026

Riverwalk Plaza
Sonesta ES Suites San Antonio Downtown Alamo Plaza

Sonesta ES Suites San Antonio Downtown Alamo Plaza

3 out of 5
425 Bonham San Antonio TX
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $112 total per night from Apr 14 to Apr 15
$112 total
Apr 14 - Apr 15
Total with taxes and fees
8.4/10 Very Good! (2,028 reviews)
Room was very clean, staff was super friendly, the location is amazing!

Reviewed on Mar 15, 2026

Sonesta ES Suites San Antonio Downtown Alamo 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
$133 nightly
The price is $185 total per night from Apr 5 to Apr 6
$185 total
Apr 5 - Apr 6
Total with taxes and fees
9.4/10 Exceptional! (2,541 reviews)
The location on the Riverwalk was great & walking to shops & restaurants

Reviewed on Mar 15, 2026

Hotel Valencia Riverwalk
See all 4,755 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

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

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

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

$36
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.