Oakland Estates Vacations from $872

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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.
Landing New Braunfels

Landing New Braunfels

4 out of 5
Price was $1,120, price is now $872 per person
$872
per person
May 17 - May 23
found 1 day ago
Roundtrip flight included
New York (NYC) to San Antonio (SAT)
No reviews
Meyer Hotel

Meyer Hotel

2 out of 5
Save 100% on your flight
Price was $1,356, price is now $984 per person
$984
per person
Apr 28 - May 3
found 19 hours ago
Roundtrip non-stop flight included
New York (NYC) to San Antonio (SAT)
9.2/10 Wonderful! (346 reviews)
Room had small issues but bed was comfortable. Staff were reallu nice

Reviewed on Feb 23, 2026

Hill Country Herb Garden

Hill Country Herb Garden

4 out of 5
Save 100% on your flight
Price was $1,358, price is now $1,031 per person
$1,031
per person
May 17 - May 23
found 1 day ago
Roundtrip flight included
New York (NYC) to San Antonio (SAT)
9.8/10 Exceptional! (217 reviews)
Clean room, amenities. Nice location. The refrigerator in the room was extremely noisy, this was the only downfall.

Reviewed on Feb 28, 2026

Signia by Hilton La Cantera Resort & Spa

Signia by Hilton La Cantera Resort & Spa

4 out of 5
La Cantera District
Price was $1,364, price is now $1,042 per person
$1,042
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Antonio (SAT)
9/10 Wonderful! (1,029 reviews)
Service was amazing, the bus driver probably made the entire trip for us super special The only downside is almost every single restaurant and bar that they advertise was closed

Reviewed on Feb 21, 2026

The Menagerie

The Menagerie

2 out of 5
Fredericksburg Historic District
Price was $1,268, price is now $975 per person
$975
per person
Apr 28 - May 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Antonio (SAT)
8.6/10 Excellent! (7 reviews)
This is now my go to place for visiting Fredericksburg. The room was outstanding, probably the best room I’ve ever stand in on a trip. The staff is friendly and helpful. This should’ve everyone’s place for visiting wine country.

Reviewed on Feb 16, 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

TownePlace Suites by Marriott San Antonio Northwest

TownePlace Suites by Marriott San Antonio Northwest

3 out of 5
5014 Prue Rd San Antonio TX
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $101 total per night from Mar 22 to Mar 23
$101 total
Mar 22 - Mar 23
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
Staff was courteous - room was for handicapped people. So when you showered water was all over the floor. Slippery and had to use towels so we wouldn’t fall . Ran out of towel paper , had to ask staff for more . Breakfast was good / decent.

Reviewed on Feb 25, 2026

TownePlace Suites by Marriott San Antonio Northwest
Crockett Hotel

Crockett Hotel

3 out of 5
320 Bonham San Antonio TX
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $129 total per night from Mar 4 to Mar 5
$129 total
Mar 4 - Mar 5
Total with taxes and fees
8.8/10 Excellent! (2,596 reviews)
Room was clean and comfortable. But there was a lot of outside noise, especially on Saturday night.

Reviewed on Mar 2, 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
$135 nightly
The price is $158 total per night from Mar 8 to Mar 9
$158 total
Mar 8 - Mar 9
Total with taxes and fees
9.4/10 Exceptional! (2,516 reviews)
This hotel is amazing. The Mexican restaurant next to the hotel was highly recommended by the hotel staff and was an excellent choice. The River Walk was adjacent to the hotel and was so much fun.

Reviewed on Mar 2, 2026

Hotel Valencia Riverwalk
See all 4,789 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

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

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

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.