Oakland Estates Vacations from $282

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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.
Crockett Hotel

Crockett Hotel

3 out of 5
Downtown San Antonio
Save 100% on your flight
Price was $395, price is now $282 per person
$282
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
8.8/10 Excellent! (2,622 reviews)
The hotel location was great, literally next door to the Alamo, easy walk to Riverwalk and other sites. The hotel rooms themselves are clean enough, but kinda tired. Valet parking is expensive ($50/night) and the app really wants you to pay a $7 tip for them to drive it a few feet from the lot. I’m happy to tip my valet, and this seemed excessive for a place that touts in and out privileges as a perk of the valet parking. The onsite tavern was hopping every night, and it was a fun atmosphere.

Reviewed on Apr 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 $1,115, price is now $724 per person
$724
per person
May 26 - May 30
found 5 hours ago
Roundtrip flight included
Chicago (CHI) to San Antonio (SAT)
8.8/10 Excellent! (1,001 reviews)
It was a beautiful hotel, easy check in, ans centrally located.

Reviewed on Mar 15, 2026

WorldMark New Braunfels

WorldMark New Braunfels

3 out of 5
Gruene
Save 100% on your flight
Price was $467, price is now $333 per person
$333
per person
Jun 24 - Jun 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9.6/10 Exceptional! (196 reviews)
This trip was amazing! We liked that the property, rooms & everything in general was very clean, and the staff was very professional. We also enjoyed the fitness center, pool & hot tub. And we were within walking distance of the Gruene historical district, restaurants and shops. We plan to return for a repeat soon!

Reviewed on Mar 14, 2026

The Kendall

The Kendall

3.5 out of 5
Save 100% on your flight
Price was $518, price is now $377 per person
$377
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Antonio (SAT)
9.6/10 Exceptional! (696 reviews)
This is our place to stay in Boerne. Great location with lots to do in walking distance: restaurants, walking trails, park, etc.

Reviewed on Apr 3, 2026

Signia by Hilton La Cantera Resort & Spa

Signia by Hilton La Cantera Resort & Spa

4 out of 5
La Cantera District
Price was $1,472, price is now $1,075 per person
$1,075
per person
May 26 - May 30
found 9 hours ago
Roundtrip flight included
Chicago (CHI) to San Antonio (SAT)
9/10 Wonderful! (1,024 reviews)
Been to this resort every year for years. We usually don’t eat on property except for Signature (amazing) and pool side. This time we decided to stay on property and to be honest not impressed at all. We skipped big breakfast and ate at Henrietta’s not good at all!! Lunch time we ate at Spitfire and had a sandwich. Service was very slow. The sandwich was good except for all the oil saturated on the bread. Dinner we ate Mexican, not impressed at all. I truly feel for the top notch hotel i feel it is the food should be also

Reviewed on Mar 29, 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 San Antonio

Downtown San Antonio

4 out of top 10 points of interest in this area
4/5(9,632 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
$85 nightly
The price is $100 total per night from May 4 to May 5
$100 total
May 4 - May 5
Total with taxes and fees
8.4/10 Very Good! (2,082 reviews)
Breakfast was fine. Did not like the $35.00 parking fee

Reviewed on Apr 4, 2026

Sonesta ES Suites San Antonio Downtown Alamo Plaza
Riverwalk Plaza

Riverwalk Plaza

4 out of 5
100 Villita Street San Antonio TX
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $117 total per night from Apr 12 to Apr 13
$117 total
Apr 12 - Apr 13
Total with taxes and fees
8/10 Very Good! (6,417 reviews)
Not sure how this hotel has a 8 star reviews. We had a huge cockroach in the room. Our shower was clogged twice and super dirty. Pictures make our room look decent but it is very old and outdated ( as well at the rest of the hotel beside the lobby ). We had a good view but it was ruined by ripped ...

Reviewed on Apr 4, 2026

Riverwalk Plaza
Crockett Hotel

Crockett Hotel

3 out of 5
320 Bonham San Antonio TX
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $123 total per night from May 3 to May 4
$123 total
May 3 - May 4
Total with taxes and fees
8.8/10 Excellent! (2,624 reviews)
We love historic hotels and understand they often come with issues. We overlook small inconveniences but do look for the staff to be present and courteous. The staff at the Crockett this weekend was hard to find and often less than friendly.

Reviewed on Apr 4, 2026

Crockett Hotel
See all 4,832 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.
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Discover the most popular places to visit in Oakland Estates

River Walk

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
River Walk in San Antonio, Texas

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 family-friendly 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 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: Botanical Garden Admission Ticket

San Antonio: Botanical Garden Admission Ticket

$18
per adult
San Antonio: Botanical Garden Admission Ticket
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.