Oakland Estates Vacations from $315

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Menger Hotel

Menger Hotel

3.5 out of 5
Downtown San Antonio
Price was $423, price is now $315 per person
$315
per person
Jun 8 - Jun 11
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9/10 Wonderful! (3,826 reviews)
Old hotel with lots of charm, great location. Bathroom was very small but beds were comfortable.

Reviewed on Apr 2, 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 $809, price is now $568 per person
$568
per person
May 28 - May 31
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

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 $733, price is now $526 per person
$526
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9/10 Wonderful! (1,504 reviews)
Only issue I had was we had to move our cookout indoors because I had to call the front desk several times to have our grill fired up, when he finally came he didn't have the lighter and the grill utensils.

Reviewed on Mar 31, 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 $899, price is now $653 per person
$653
per person
Jun 8 - Jun 11
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
8.8/10 Excellent! (1,001 reviews)
It was a beautiful hotel, easy check in, ans centrally located.

Reviewed on Mar 15, 2026

Hotel Contessa

Hotel Contessa

4 out of 5
Downtown San Antonio
Save 100% on your flight
Price was $595, price is now $443 per person
$443
per person
Jun 8 - Jun 11
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9/10 Wonderful! (3,491 reviews)
Nice location, friendly staff, room was okay but not as clean as I am used to from previous stays there. Had to wait an hour past Check-in time for room to be ready- not worth the almost $500 we paid for one night stay (with valet parking).

Reviewed on Mar 30, 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

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
$93 nightly
The price is $110 total per night from Apr 6 to Apr 7
$110 total
Apr 6 - Apr 7
Total with taxes and fees
8.4/10 Very Good! (2,077 reviews)
Very nice room with great attached parking garage. Close to Riverwalk.

Reviewed on Mar 31, 2026

Sonesta ES Suites San Antonio Downtown Alamo Plaza
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! (6,407 reviews)
The rooms and bathrooms are old and need some repairs

Reviewed on Apr 1, 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
$171 nightly
The price is $202 total per night from Apr 5 to Apr 6
$202 total
Apr 5 - Apr 6
Total with taxes and fees
9.4/10 Exceptional! (2,607 reviews)
Wonderful, close to everything, right on Riverwalk

Reviewed on Apr 2, 2026

Hotel Valencia Riverwalk
See all 4,821 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

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: 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
The Undead: Zombie Apocalypse Escape Room at Extreme Escape

The Undead: Zombie Apocalypse Escape Room at Extreme Escape

$32
per adult
The Undead: Zombie Apocalypse Escape Room at Extreme Escape
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.