Oakland Estates Vacations from $265

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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.
San Antonio Marriott Northwest Medical Center

San Antonio Marriott Northwest Medical Center

3.5 out of 5
Medical Center District
Save 100% on your flight
Price was $393, price is now $265 per person
$265
per person
May 7 - May 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
8.6/10 Excellent! (1,003 reviews)
My stay at the hotel was excellent. It was my lady’s birthday and they sent a special package for her. Truly appreciate the gesture, the hotel staff and cleanliness of the room. I will definitely be back when next we visit San Antonio.

Reviewed on Mar 4, 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 $1,629, price is now $1,049 per person
$1,049
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9/10 Wonderful! (1,026 reviews)
Staff friendly. Feel safe with a guarded community. Clean rooms. Beautiful grounds with pools and fire pits. Hot tub not working for a while but staff worked hard to get it up and running within 24 hours.

Reviewed on Mar 1, 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 $679, price is now $459 per person
$459
per person
Apr 18 - Apr 21
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
8.8/10 Excellent! (1,000 reviews)
Lobby was absolutely beautiful!

Reviewed on Feb 23, 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 $573, price is now $396 per person
$396
per person
May 7 - May 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9/10 Wonderful! (1,477 reviews)
A lite resort feel that is affordable.

Reviewed on Mar 4, 2026

Menger Hotel

Menger Hotel

3.5 out of 5
Downtown San Antonio
Save 100% on your flight
Price was $569, price is now $394 per person
$394
per person
May 7 - May 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9/10 Wonderful! (3,794 reviews)
Our stay was awesome!

Reviewed on Mar 1, 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
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

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: 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.