Oakland Estates Vacations from $489

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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.
Tx Home Group- San Antonio

Tx Home Group- San Antonio

3 out of 5
Midtown
Price was $655, price is now $489 per person
$489
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to San Antonio (SAT)
10/10 Exceptional! (2 reviews)
Great place to stay. Host really made you feel comfortable and welcomed.

Reviewed on Jul 28, 2025

Tapatio Springs Hill Country Resort

Tapatio Springs Hill Country Resort

4 out of 5
Price was $861, price is now $617 per person
$617
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to San Antonio (SAT)
8.6/10 Excellent! (797 reviews)
Rooms need to be updated

Reviewed on Aug 27, 2025

TimberRose B&B

TimberRose B&B

3.5 out of 5
Price was $985, price is now $718 per person
$718
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to San Antonio (SAT)
9.8/10 Exceptional! (58 reviews)
The property is peaceful and so cozy. Located perfectly between the wine trail and downtown, it is the IDEAL setting! All the conveniences of home, clean, comfortable and a true relaxation destination.

Reviewed on Jan 2, 2024

Albert Hotel

Albert Hotel

4 out of 5
Fredericksburg Historic District
Price was $1,352, price is now $1,044 per person
$1,044
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to San Antonio (SAT)
9.2/10 Wonderful! (160 reviews)
Very convenient location. The room was very nice but it was very noisy. Can hear everyone in the hallway and next door in the other rooms.

Reviewed on Aug 25, 2025

Onera Fredericksburg

Onera Fredericksburg

2 out of 5
Save 100% on your flight
Price was $1,672, price is now $1,318 per person
$1,318
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to San Antonio (SAT)
9.2/10 Wonderful! (18 reviews)
I loved the rooms setting with the wide windows offering a wonderful view to wildlife nature. Also loved the private hot tube right outside the room.

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

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 refundable
$134 nightly
The price is $159 total per night from Sep 15 to Sep 16
$159 total
Sep 15 - Sep 16
Total with taxes and fees
9/10 Wonderful! (952 reviews)
"The hotel was very nice, quiet, and clean, providing a comfortable stay. The staff was friendly and welcoming, which made the experience even better. I would recommend this hotel to anyone looking for a relaxing and pleasant stay."

Reviewed on Aug 27, 2025

Hyatt Vacation Club at Wild Oak Ranch, San Antonio
Riverwalk Plaza

Riverwalk Plaza

4 out of 5
100 Villita Street, Dwyer/Main Plaza, San Antonio, TX
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $117 total per night from Sep 1 to Sep 2
$117 total
Sep 1 - Sep 2
Total with taxes and fees
8/10 Very Good! (5,746 reviews)
"Everything is ok"

Reviewed on Aug 26, 2025

Riverwalk Plaza
Spark By Hilton San Antonio Northwest near Six Flags

Spark By Hilton San Antonio Northwest near Six Flags

3 out of 5
6755 North Loop 1604 West, San Antonio, TX
Fully refundableReserve now, pay when you stay
$60 nightly
The price is $71 total per night from Sep 7 to Sep 8
$71 total
Sep 7 - Sep 8
Total with taxes and fees
7.8/10 Good! (1,511 reviews)
"The room was clean and a/c worked very well. The only bad things is that the hallways are hot except for the 1st floor hallway."

Reviewed on Aug 25, 2025

Spark By Hilton San Antonio Northwest near Six Flags
See all 4,595 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
Lackland Air Force Base

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
Six Flags Fiesta Texas

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 entertainment choices in this family-friendly area.

Six Flags Fiesta Texas

Things to do

San Antonio: Discovery Tour at Natural Bridge Caverns

San Antonio: Discovery Tour at Natural Bridge Caverns

$36
per adult
92% of travellers recommend
San Antonio: Discovery Tour at Natural Bridge Caverns
SEA LIFE San Antonio

SEA LIFE San Antonio

$25
per adult
78% of travellers recommend
SEA LIFE San Antonio
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.