Oakland Estates Vacations from $129

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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.
GO2 Inn & Suites by Relianse

GO2 Inn & Suites by Relianse

2.5 out of 5
Harlandale
Save 100% on your flight
Price was $222, price is now $129 per person
$129
per person
May 23 - May 26
found 3 hours ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
2.6/10 (8 reviews)
When we arrived to the property there was a sign on the door that said they had limited availability due to being under construction. However the area felt unsafe the manager did state they had no rooms available. That it was a system error on behalf Expedia she did not understand why they allowed me to book. She then gave me a letter stating I canceled the room. Instead of stating why we did not stay there the letter stated other wise. Just crossing my fingers I don’t get charged by the property. Other than that it is under construction this would be for someone that is single if they decide to stay there.

Reviewed on Aug 11, 2025

Signia by Hilton La Cantera Resort & Spa

Signia by Hilton La Cantera Resort & Spa

4 out of 5
La Cantera District
Price was $1,520, price is now $753 per person
$753
per person
Jun 11 - Jun 17
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9/10 Wonderful! (1,024 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

Tx Home Group- San Antonio

Tx Home Group- San Antonio

2 out of 5
Midtown
Save 100% on your flight
Price was $682, price is now $413 per person
$413
per person
Jun 15 - Jun 17
found 1 day ago
Roundtrip flight included
Denver (DEN) 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

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
Save 100% on your flight
Price was $542, price is now $329 per person
$329
per person
May 23 - May 26
found 3 hours ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9/10 Wonderful! (1,541 reviews)
The check in process needs improvement. Waited in long line to be told our room wasn’t ready. Then another line with the concierge to get our parking pass. Then yet another line at 4:00 to get our room key. All total about an hour. Seems lengthly and unnecessary. And to top it off the room keys didn’t work so had to go back to get new ones. An apology would have been nice.

Reviewed on Apr 6, 2026

The Continental, powered by Placemakr - Downtown - Market Square

The Continental, powered by Placemakr - Downtown - Market Square

3.5 out of 5
Downtown San Antonio
Save 100% on your flight
Price was $1,052, price is now $708 per person
$708
per person
Jun 11 - Jun 17
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9.6/10 Exceptional! (84 reviews)
I loved the amenities of the room.

Reviewed on Apr 6, 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 12 to Apr 13
$117 total
Apr 12 - Apr 13
Total with taxes and fees
8/10 Very Good! (6,428 reviews)
Slow service at restaurant.

Reviewed on Apr 6, 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
$85 nightly
The price is $100 total per night from May 7 to May 8
$100 total
May 7 - May 8
Total with taxes and fees
8.4/10 Very Good! (2,091 reviews)
The room was clean but definitely had a extremely strong men's musk cologne type smell in it, which made you think they might be hiding something as far as cleanliness, or mold scent or something like that. The hotel parking was crazy, for me because they claimed to have parking for oversized vehicles ...

Reviewed on Apr 5, 2026

Sonesta ES Suites San Antonio Downtown Alamo Plaza
Drury Plaza Hotel San Antonio Riverwalk

Drury Plaza Hotel San Antonio Riverwalk

3 out of 5
105 S Saint Marys Street San Antonio TX
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $151 total per night from Apr 12 to Apr 13
$151 total
Apr 12 - Apr 13
Total with taxes and fees
9.4/10 Exceptional! (4,441 reviews)
Staff was absolutely amazing. While this stay was a bit pricey compared to others on our trip-the location made up for it. We appreciate the old pictures showing the transformation of the building from a historic bank into a classy hotel. Ended up booking an additional Drury stay in Louisiana just ...

Reviewed on Apr 6, 2026

Drury Plaza Hotel San Antonio Riverwalk
See all 4,832 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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Kid Friendly Vacations

Discover the most popular places to visit in Oakland Estates

River Walk

River Walk

4.5/5(7,401 reviews)

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

River Walk
River Walk in San Antonio, Texas

Lackland Air Force Base

4.5/5(1,270 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 acclaimed theater scene and entertainment choices 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: Botanical Garden Admission Ticket

San Antonio: Botanical Garden Admission Ticket

$18
per adult
San Antonio: Botanical Garden Admission Ticket
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.