Oakland Estates Vacations from $388

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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
Save 100% on your flight
Price was $543, price is now $388 per person
$388
per person
May 5 - May 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
7.8/10 Good! (1,027 reviews)
Staff was great and breakfast was a family hit (included in the stay) good area and clean rooms. Blinds were broken, tv channels where limited, building is fairly outdated and aged. The building layout is cramped and inconvenient. Only real negative to hold against them though was the shower head was abysmal in terms of functionality and water pressure.

Reviewed on Feb 10, 2026

 Landing Apartments San Antonio Northeast

 Landing Apartments San Antonio Northeast

3 out of 5
Save 100% on your flight
Price was $806, price is now $544 per person
$544
per person
May 5 - May 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
No reviews
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 $783, price is now $539 per person
$539
per person
May 5 - May 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9.6/10 Exceptional! (56 reviews)
Everything was excellent.

Reviewed on Feb 9, 2026

Menger Hotel

Menger Hotel

3.5 out of 5
Downtown San Antonio
Save 100% on your flight
Price was $581, price is now $402 per person
$402
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9/10 Wonderful! (3,521 reviews)
The hotel was beyond my expectations. The rooms were clean, friendly staff, very well maintained.

Reviewed on Feb 16, 2026

Club Wyndham La Cascada

Club Wyndham La Cascada

4 out of 5
Downtown San Antonio
Save 100% on your flight
Price was $1,031, price is now $739 per person
$739
per person
May 5 - May 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
8.4/10 Very Good! (180 reviews)
My family and I had a lovely weekend. The view from my balcony was so beautiful and very peaceful. Overall wonderful stay!

Reviewed on Aug 22, 2025

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

Crockett Hotel

Crockett Hotel

3 out of 5
320 Bonham San Antonio TX
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $111 total per night from Mar 2 to Mar 3
$111 total
Mar 2 - Mar 3
Total with taxes and fees
8.8/10 Excellent! (2,562 reviews)
Great location. Historic feeling.

Reviewed on Feb 17, 2026

Crockett Hotel
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
$145 nightly
The price is $171 total per night from Mar 8 to Mar 9
$171 total
Mar 8 - Mar 9
Total with taxes and fees
9.4/10 Exceptional! (2,479 reviews)
A great hotel experience all the way around! Friendly, considerate and helpful staff everywhere. Beautiful seating spaces, restaurant, patio and bar. The rooms as well were spacious, clean, quiet and comfortable. It was a perfect spot on the riverwalk!

Reviewed on Feb 17, 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
$121 nightly
The price is $143 total per night from Feb 22 to Feb 23
$143 total
Feb 22 - Feb 23
Total with taxes and fees
9/10 Wonderful! (1,453 reviews)
This is a timeshare scam . Do not fall for it , do not go to the presentation .

Reviewed on Feb 16, 2026

Hyatt Vacation Club at Wild Oak Ranch, San Antonio
See all 4,797 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 walkable 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 lively festivals and acclaimed theater scene in this family-friendly area.

Six Flags Fiesta Texas

Things to do

San Antonio: Tower of the Americas Entry Ticket

San Antonio: Tower of the Americas Entry Ticket

$21
per adult
San Antonio: Tower of the Americas Entry Ticket
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.