Oakland Estates Vacations from $325

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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 $412, price is now $325 per person
$325
per person
May 6 - May 9
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to San Antonio (SAT)
7.8/10 Good! (1,082 reviews)
The receiving staff was awesome, greeted me and made me very comfortable since I got the 3 hour early, directed me to have lunch while securing my suitcase. On my return, she booked me in two hours early. The room, very spacious and clean and the breakfast was not bad. Would love for them to add a restaurant to the property and service.

Reviewed on Mar 17, 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 $1,238, price is now $856 per person
$856
per person
Apr 26 - May 2
found 13 hours 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

The Continental, powered by Placemakr - Downtown - Market Square

The Continental, powered by Placemakr - Downtown - Market Square

3.5 out of 5
Downtown San Antonio
Price was $938, price is now $695 per person
$695
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9.6/10 Exceptional! (84 reviews)
nice locations pretty quiet

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
Price was $1,139, price is now $858 per person
$858
per person
May 30 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to San Antonio (SAT)
9/10 Wonderful! (1,031 reviews)
Overall good stay. Would definitely stay there again

Reviewed on Mar 9, 2026

The Inn at Market Square

The Inn at Market Square

3 out of 5
Downtown San Antonio
Price was $1,527, price is now $1,171 per person
$1,171
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to San Antonio (SAT)
4/10 (661 reviews)
It was all good staff and room

Reviewed on Feb 17, 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
$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! (6,386 reviews)
Very clean room. Amazing location

Reviewed on Mar 18, 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! (2,554 reviews)
1st time visitors to San Antonio. The hotel is perfectly located to the River Walk & The Alamo, and very walkable. Our biggest complaint is with the room temperature. It was very warm & made sleeping and getting ready in a ventless bathroom quite uncomfortable.

Reviewed on Mar 18, 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! (1,517 reviews)
This is my third time staying here and I have definitely noticed a few things have changed and not for the better. Just seemed to me the customer has to suffer with minimal housekeeping and not the customer service there was before.

Reviewed on Mar 18, 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

4.5/5(7,278 reviews)

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

4.5/5(1,254 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(970 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

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.