Oakland Estates Vacations from $726

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.
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 $1,024, price is now $726 per person
$726
per person
May 8 - May 14
found 2 days ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Antonio (SAT)
9/10 Wonderful! (1,541 reviews)
So peaceful! Great resort and has amazing pools!

Reviewed on Apr 4, 2026

Tx Home Group- San Antonio

Tx Home Group- San Antonio

2 out of 5
Midtown
Save 100% on your flight
Price was $1,134, price is now $824 per person
$824
per person
May 30 - Jun 3
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) 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

Signia by Hilton La Cantera Resort & Spa

Signia by Hilton La Cantera Resort & Spa

4 out of 5
La Cantera District
Price was $1,472, price is now $1,075 per person
$1,075
per person
May 26 - May 30
found 2 hours ago
Roundtrip flight included
Chicago (CHI) 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

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 $1,086, price is now $813 per person
$813
per person
Jun 4 - Jun 8
found 9 hours ago
Roundtrip flight included
Chicago (CHI) 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

WorldMark New Braunfels

WorldMark New Braunfels

3 out of 5
Gruene
Price was $1,050, price is now $787 per person
$787
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to San Antonio (SAT)
9.6/10 Exceptional! (196 reviews)
This trip was amazing! We liked that the property, rooms & everything in general was very clean, and the staff was very professional. We also enjoyed the fitness center, pool & hot tub. And we were within walking distance of the Gruene historical district, restaurants and shops. We plan to return for a repeat soon!

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

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
$94 nightly
The price is $111 total per night from May 5 to May 6
$111 total
May 5 - May 6
Total with taxes and fees
8.4/10 Very Good! (2,080 reviews)
Great location, parking is expensive but most places are, we parked elsewhere for cheaper. Good breakfast and pool area.

Reviewed on Apr 4, 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
$98 nightly
The price is $116 total per night from Apr 6 to Apr 7
$116 total
Apr 6 - Apr 7
Total with taxes and fees
8/10 Very Good! (6,415 reviews)
Nice but an older building. Great location.

Reviewed on Apr 4, 2026

Riverwalk Plaza
Crockett Hotel

Crockett Hotel

3 out of 5
320 Bonham San Antonio TX
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $96 total per night from Apr 5 to Apr 6
$96 total
Apr 5 - Apr 6
Total with taxes and fees
8.8/10 Excellent! (2,622 reviews)
Loved the restaurant food and drinks, easy to walk to places

Reviewed on Apr 3, 2026

Crockett Hotel
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.
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(7,401 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 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: 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.