Oakland Estates Vacations from $390

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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 $504, price is now $390 per person
$390
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Chicago (CHI) to San Antonio (SAT)
7.8/10 Good! (1,081 reviews)
Hotel property was very clean and the location was easy access to everything. Customer service was HORRIBLE. Every shift and including the kitchen staff was horrible

Reviewed on Mar 10, 2026

Signia by Hilton La Cantera Resort & Spa

Signia by Hilton La Cantera Resort & Spa

4 out of 5
La Cantera District
Price was $853, price is now $633 per person
$633
per person
Apr 30 - May 2
found 15 hours ago
Roundtrip flight included
Chicago (CHI) to San Antonio (SAT)
9/10 Wonderful! (1,026 reviews)
Overall good stay. Would definitely stay there again

Reviewed on Mar 9, 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 $872, price is now $651 per person
$651
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Antonio (SAT)
8.8/10 Excellent! (1,002 reviews)
Lobby was absolutely beautiful!

Reviewed on Feb 23, 2026

 Landing Apartments San Antonio Northeast

 Landing Apartments San Antonio Northeast

3 out of 5
Price was $1,096, price is now $841 per person
$841
per person
May 20 - May 27
found 22 hours ago
Roundtrip flight included
Chicago (CHI) to San Antonio (SAT)
No reviews
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 $961, price is now $750 per person
$750
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Chicago (CHI) to San Antonio (SAT)
9/10 Wonderful! (1,490 reviews)
The pool was nice and staff was friendly. We enjoyed our stay. We just wished the weather was better. It rained the entire trip but the staff was accommodating with other activities.

Reviewed on Mar 9, 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

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 7 to Apr 8
$110 total
Apr 7 - Apr 8
Total with taxes and fees
8.4/10 Very Good! (2,024 reviews)
Well they do charge for parking. There’s that. I guess since they are downtown San Antonio. Or you can frantically look for parking on the street that you have to pay for but free on Sunday. Quaint location, I must say with short walking distance to everything. Banks, the Alamo, food, shopping, the ...

Reviewed on Mar 10, 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
$119 nightly
The price is $141 total per night from Apr 5 to Apr 6
$141 total
Apr 5 - Apr 6
Total with taxes and fees
8/10 Very Good! (6,426 reviews)
Excellent!

Reviewed on Mar 10, 2026

Riverwalk Plaza
Crockett Hotel

Crockett Hotel

3 out of 5
320 Bonham San Antonio TX
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $146 total per night from Mar 31 to Apr 1
$146 total
Mar 31 - Apr 1
Total with taxes and fees
8.8/10 Excellent! (2,610 reviews)
Very close to The Alamo, restaurants and the River Walk. Valet parking was great. Staff super friendly.

Reviewed on Mar 9, 2026

Crockett Hotel
See all 4,717 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.