Oakland Estates Vacations from $426

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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.
Staybridge Suites San Antonio by IHG

Staybridge Suites San Antonio by IHG

3 out of 5
Uptown
Price was $536, price is now $426 per person
$426
per person
Jun 3 - Jun 7
found 14 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to San Antonio (SAT)
8.4/10 Very Good! (1,001 reviews)
Wonderful and pleasant staff.

Reviewed on Feb 18, 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 $1,015, price is now $731 per person
$731
per person
May 20 - May 23
found 3 hours ago
Roundtrip flight included
Los Angeles (LAX) to San Antonio (SAT)
9/10 Wonderful! (1,031 reviews)
Been to this resort every year for years. We usually don’t eat on property except for Signature (amazing) and pool side. This time we decided to stay on property and to be honest not impressed at all. We skipped big breakfast and ate at Henrietta’s not good at all!! Lunch time we ate at Spitfire and had a sandwich. Service was very slow. The sandwich was good except for all the oil saturated on the bread. Dinner we ate Mexican, not impressed at all. I truly feel for the top notch hotel i feel it is the food should be also

Reviewed on Mar 29, 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 $1,123, price is now $849 per person
$849
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip flight included
New York (NYC) 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

Onera Fredericksburg

Onera Fredericksburg

4 out of 5
Price was $1,566, price is now $1,232 per person
$1,232
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip flight included
New York (NYC) to San Antonio (SAT)
9.2/10 Wonderful! (61 reviews)
Outstanding experience! Stayed in the Monolith unit … the feeling of sleeping in the trees was wonderful! Loved relaxing in the hot tub at night while enjoying the star filled sky! The staff was so very helpful. On a scale of 1 to 5 I rate it a10. It exceeded my expectations… I will absolutely stay here again!!

Reviewed on Mar 27, 2026

Tx Home Group- San Antonio

Tx Home Group- San Antonio

2 out of 5
Midtown
Price was $885, price is now $707 per person
$707
per person
May 13 - May 16
found 9 hours ago
Roundtrip non-stop 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! (6,421 reviews)
Had a great time

Reviewed on Mar 30, 2026

Riverwalk Plaza
Hotel Valencia Riverwalk

Hotel Valencia Riverwalk

4.5 out of 5
150 E Houston St San Antonio TX
$150 nightly
The price is $177 total per night from Apr 26 to Apr 27
$177 total
Apr 26 - Apr 27
Total with taxes and fees
9.4/10 Exceptional! (2,595 reviews)
Excellent hotel !! loved the extra touches and location!

Reviewed on Mar 30, 2026

Hotel Valencia Riverwalk
Menger Hotel

Menger Hotel

3.5 out of 5
204 Alamo Plaza San Antonio TX
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $129 total per night from Apr 7 to Apr 8
$129 total
Apr 7 - Apr 8
Total with taxes and fees
9/10 Wonderful! (3,875 reviews)
This hotel was a wonderful departure from the cookie cutter hotels you see now. The history shines through, and it is still very well maintained with modern amenities.

Reviewed on Mar 30, 2026

Menger Hotel
See all 4,735 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.
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All Inclusive Vacations
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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

San Antonio Zoo Any Day Ticket including ZooLights

San Antonio Zoo Any Day Ticket

$30
per adult
96% of travellers recommend
San Antonio Zoo Any Day Ticket
SEA LIFE San Antonio

SEA LIFE San Antonio

$28
per adult
78% of travellers recommend
SEA LIFE San Antonio
San Antonio Old Town Trolley Hop-on Hop-Off Tour

San Antonio Old Town Trolley Hop-on Hop-Off Tour

$54
per adult
92% of travellers recommend
San Antonio Old Town Trolley Hop-on Hop-Off Tour
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.