Oakland Estates Vacations from $264

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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.
OYO Inn & Suites Medical Center San Antonio

OYO Inn & Suites Medical Center San Antonio

2 out of 5
Medical Center District
Save 100% on your flight
Price was $355, price is now $264 per person
$264
per person
Apr 23 - Apr 28
found 20 hours ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
7.2/10 Good! (229 reviews)
Staff was courteous and professional and the room is nice.

Reviewed on Dec 29, 2025

Hampton Inn San Antonio Stone Oak

Hampton Inn San Antonio Stone Oak

2.5 out of 5
Uptown
Save 100% on your flight
Price was $424, price is now $280 per person
$280
per person
Apr 23 - Apr 28
found 20 hours ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
8.4/10 Very Good! (788 reviews)
Front clerk old guy was rude, the lady was really nice. Pool dirty look black , breakfast was fantastic , my bathtub when ever we took a shower the water wasn't draining it was stuck . The lady doing breakfast was working by herself on sunday morning did a great job even when some random lady was being rude to her and recording her she still was nice and working hard. This lady went to go have breakfast almost at 10:00 if you want breakfast get up earlier dont need to be rude to the employee's.

Reviewed on Mar 17, 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 $1,082, price is now $751 per person
$751
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Denver (DEN) 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
Save 100% on your flight
Price was $627, price is now $469 per person
$469
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Denver (DEN) 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

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
Price was $839, price is now $632 per person
$632
per person
May 20 - May 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Antonio (SAT)
9/10 Wonderful! (1,504 reviews)
The amenities are awesome but the rooms are showing their age. Paint overspray everywhere, our toilet ran, the shower pull was frozen and the GFCI plug in the bathroom was nonfunctional. They fixed the shower first day but everything else remained. Brautiful setting...

Reviewed on Mar 19, 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! (6,397 reviews)
El staff le falta preparación. Los pasillos sucios. El desayuno mediocre. Expedia me cobró por 3 habitaciones 608.00, cuando llegué al hotel un enrredo horrible.

Reviewed on Mar 19, 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
$165 nightly
The price is $194 total per night from Mar 22 to Mar 23
$194 total
Mar 22 - Mar 23
Total with taxes and fees
9.4/10 Exceptional! (2,555 reviews)
From the moment we arrived everyone from the valet to the hotel staff greeted you with a friendly smile. The location was perfect. The Majestic theater was less then a two minute walk away. Plenty of places to eat or grab a drink. Without thinking twice about it. I would stay here again.

Reviewed on Mar 20, 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
$131 nightly
The price is $155 total per night from Apr 13 to Apr 14
$155 total
Apr 13 - Apr 14
Total with taxes and fees
9/10 Wonderful! (1,520 reviews)
Great area! Makes you feel like you're 100 miles from the city.

Reviewed on Mar 19, 2026

Hyatt Vacation Club at Wild Oak Ranch, San Antonio
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.