Oakland Estates Vacations from $276

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
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 $390, price is now $276 per person
$276
per person
Apr 14 - Apr 17
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9.6/10 Exceptional! (81 reviews)
Very impressed with this place. Had everything you need!! With just 10 minues walk from the river aswell. !! ONLY Recormendation is curtains for night time !!

Reviewed on Mar 3, 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 $647, price is now $428 per person
$428
per person
Apr 18 - Apr 21
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
8.8/10 Excellent! (1,002 reviews)
Lobby was absolutely beautiful!

Reviewed on Feb 23, 2026

The Inn at Market Square

The Inn at Market Square

3 out of 5
Downtown San Antonio
Save 100% on your flight
Price was $1,979, price is now $1,425 per person
$1,425
per person
Apr 11 - Apr 17
found 1 day ago
Roundtrip flight included
New York (NYC) to San Antonio (SAT)
4/10 (660 reviews)
It was all good staff and room

Reviewed on Feb 17, 2026

Hotel Contessa

Hotel Contessa

4 out of 5
Downtown San Antonio
Price was $660, price is now $494 per person
$494
per person
May 14 - May 17
found 7 hours ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9/10 Wonderful! (3,475 reviews)
Did not experience the pool

Reviewed on Mar 7, 2026

Signia by Hilton La Cantera Resort & Spa

Signia by Hilton La Cantera Resort & Spa

4 out of 5
La Cantera District
Price was $1,091, price is now $830 per person
$830
per person
May 14 - May 17
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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

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

Sonesta ES Suites San Antonio Downtown Alamo Plaza

Sonesta ES Suites San Antonio Downtown Alamo Plaza

3 out of 5
425 Bonham San Antonio TX
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $99 total per night from Mar 10 to Mar 11
$99 total
Mar 10 - Mar 11
Total with taxes and fees
8.4/10 Very Good! (2,018 reviews)
Nice staff and clean rooms.

Reviewed on Mar 7, 2026

Sonesta ES Suites San Antonio Downtown Alamo Plaza
Crockett Hotel

Crockett Hotel

3 out of 5
320 Bonham San Antonio TX
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $140 total per night from Mar 16 to Mar 17
$140 total
Mar 16 - Mar 17
Total with taxes and fees
8.8/10 Excellent! (2,605 reviews)
The staff went above and beyond to bake our stay wonderful!

Reviewed on Mar 7, 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
$142 nightly
The price is $166 total per night from Apr 5 to Apr 6
$166 total
Apr 5 - Apr 6
Total with taxes and fees
9.4/10 Exceptional! (2,534 reviews)
Nice but kinda a dark ole renovated hotel - very little room for drop off outside, convenient to river walk , but we’d rather not be in the heart of it contessa is better option

Reviewed on Mar 7, 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

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 family-friendly 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 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

$36
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.