Oakland Estates Vacations from $486

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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 Resort at Schlitterbahn

The Resort at Schlitterbahn

3.5 out of 5
Eastside
Price was $623, price is now $486 per person
$486
per person
May 22 - May 25
found 14 hours ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
8.6/10 Excellent! (1,007 reviews)
I loved the location. Be sure to check for the water park before booking because it doesn’t run all year long. The nature and river was beautiful and could see deers from our rooms even during the day.

Reviewed on Mar 22, 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 $1,727, price is now $1,249 per person
$1,249
per person
Jun 7 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Antonio (SAT)
9/10 Wonderful! (1,031 reviews)
Clean room | Amazing staff |

Reviewed on Mar 19, 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 $1,348, price is now $1,020 per person
$1,020
per person
Jun 7 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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

The Inn at Market Square

The Inn at Market Square

3 out of 5
Downtown San Antonio
Price was $956, price is now $736 per person
$736
per person
May 5 - May 7
found 4 hours ago
Roundtrip flight included
Boston (BOS) to San Antonio (SAT)
4/10 (661 reviews)
It was all good staff and room

Reviewed on Feb 17, 2026

Hotel Contessa

Hotel Contessa

4 out of 5
Downtown San Antonio
Price was $1,218, price is now $968 per person
$968
per person
Jun 7 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Antonio (SAT)
9/10 Wonderful! (3,491 reviews)
The hotel, staff, drinks and food are excellent.. the only thing they don’t have a little store inside that sells amenities and it’s self parking outside and the charge 30 bucks a night

Reviewed on Mar 22, 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! (6,403 reviews)
I had to call the front desk to get the room cleaned after 2 days I not having room service.

Reviewed on Mar 21, 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! (2,562 reviews)
Fun times

Reviewed on Mar 21, 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
$133 nightly
The price is $158 total per night from Apr 13 to Apr 14
$158 total
Apr 13 - Apr 14
Total with taxes and fees
9/10 Wonderful! (1,521 reviews)
Great hotel with very clean, comfortable rooms and excellent attention to detail. The staff was incredibly friendly, professional, and always willing to help with a smile. They made our stay feel welcoming and stress-free. Highly recommended — we will definitely be coming back!

Reviewed on Mar 21, 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

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.