Oakland Estates Vacations from $227

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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.
Oyo Hotel San Antonio Lackland AFB/Seaworld Hwy 90 W

Oyo Hotel San Antonio Lackland AFB/Seaworld Hwy 90 W

2 out of 5
Price was $304, price is now $227 per person
$227
per person
May 5 - May 9
found 17 hours ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
6.6/10 (408 reviews)
Office Had The Greatest Hospitality That I Have Ever Received In Any 5 Star Hotel Not To Mention Their Staff Was Wonderful And Very Quick To Get You Any Amenities Required. The Rooms Where So Spotless That You Could Even Eat Off The Floor.I Highly Recommend This OYO Motel.Thanks Again To The Management & Employees.Keep Up The Good Work.Sincerely, Happy Guest # 117

Reviewed on Jan 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 $696, price is now $497 per person
$497
per person
May 5 - May 9
found 17 hours ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
8.8/10 Excellent! (1,004 reviews)
It was a beautiful hotel, easy check in, ans centrally located.

Reviewed on Mar 15, 2026

Tx Home Group- San Antonio

Tx Home Group- San Antonio

2 out of 5
Midtown
Save 100% on your flight
Price was $798, price is now $573 per person
$573
per person
May 5 - May 9
found 17 hours ago
Roundtrip flight included
Denver (DEN) 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

The Continental, powered by Placemakr - Downtown - Market Square

The Continental, powered by Placemakr - Downtown - Market Square

3.5 out of 5
Downtown San Antonio
Price was $809, price is now $610 per person
$610
per person
Apr 24 - Apr 26
found 1 hour ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9.6/10 Exceptional! (84 reviews)
nice locations pretty quiet

Reviewed on Mar 14, 2026

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 $351, price is now $265 per person
$265
per person
May 5 - May 9
found 17 hours ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
7.8/10 Good! (1,082 reviews)
Dirty towels left in the bathroom.

Reviewed on Mar 19, 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(9,564 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

Riverwalk Plaza

Riverwalk Plaza

4 out of 5
100 Villita Street San Antonio TX
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $118 total per night from Apr 5 to Apr 6
$118 total
Apr 5 - Apr 6
Total with taxes and fees
8/10 Very Good! (6,412 reviews)
Good hospitable staff.

Reviewed on Mar 23, 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
$162 nightly
The price is $191 total per night from Mar 31 to Apr 1
$191 total
Mar 31 - Apr 1
Total with taxes and fees
9.4/10 Exceptional! (2,570 reviews)
This hotel is always clean and the staff is always extremely helpful. I’ll be back again for sure!

Reviewed on Mar 23, 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
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $159 total per night from Apr 13 to Apr 14
$159 total
Apr 13 - Apr 14
Total with taxes and fees
9/10 Wonderful! (1,521 reviews)
Great hotel with very clean, comfortable rooms and excellent attention to detail. The staff was incredibly friendly, professional, and always willing to help with a smile. They made our stay feel welcoming and stress-free. Highly recommended — we will definitely be coming back!

Reviewed on Mar 21, 2026

Hyatt Vacation Club at Wild Oak Ranch, San Antonio
See all 4,743 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(7,291 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(1,257 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(972 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

$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.