Lakeside Vacation Packages

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Your Lakeside Vacation

With everything organized before you take off, our Lakeside vacation packages mean you can focus more on enjoying your getaway. Whether you're staying in the neighborhood of Timberlake Village, which is good for views, or another part of town, this fun city offers a world of discoveries. If a sightseeing tour is on the agenda during your trip to Lakeside, swing by popular attractions like Bagnell Dam, Lake of the Ozarks and Bagnell Dam Viewpoint and Osage National Golf Club. Expedia is here to help you escape your routine. Tailor your vacation to Lakeside to suit your style of travel, whatever that may look like.

Top Lakeside Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo St Louis - Central West End by IHG

Hotel Indigo St Louis - Central West End by IHG

3.5 out of 5
Central West End
Price was CA $1,155, price is now CA $881 per person
CA $881
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
8.2/10 Very Good! (1,000 reviews)
Just a really cool place. One of the cleanest hotels I've stayed in i St Louis. Everyone was really friendly.

Reviewed on Feb 6, 2026

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was CA $2,070, price is now CA $1,197 per person
CA $1,197
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
9.2/10 Wonderful! (1,600 reviews)
Great room and friendly staff in a nice area. Will come again.

Reviewed on Feb 11, 2026

Hotel Saint Louis, Autograph Collection

Hotel Saint Louis, Autograph Collection

4 out of 5
Downtown St. Louis
Price was CA $1,779, price is now CA $1,349 per person
CA $1,349
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
8.8/10 Excellent! (458 reviews)
Property and room was really nice. I will be staying here in the future

Reviewed on Nov 25, 2025

Hilton Garden Inn St. Louis/O'Fallon MO

Hilton Garden Inn St. Louis/O'Fallon MO

3 out of 5
Price was CA $1,440, price is now CA $1,132 per person
CA $1,132
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
8.8/10 Excellent! (705 reviews)
Everything was great. The hotel smelled very fresh and clean when we walked into the lobby. The room was clean. Staff was friendly

Reviewed on Feb 11, 2026

The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Price was CA $1,236, price is now CA $988 per person
CA $988
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
9.4/10 Exceptional! (425 reviews)
Very friendly and helpful front desk staff and restaurant staff. Lovely experience!

Reviewed on Feb 4, 2026

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Lakeside Hotel Deals

Lodge Of Four Seasons Golf Resort, Marina & Spa

Lodge Of Four Seasons Golf Resort, Marina & Spa

4 out of 5
315 Four Seasons Dr. Lake Ozark MO
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Feb 15 to Feb 16
CA $118
CA $161 total
Feb 15 - Feb 16
includes taxes & fees
7.2/10 Good! (1,096 reviews)
We have stayed here many times for gymnastics, just love it. The only issue I have ever had was this time at check in, when I book I normally choose the outside lake view lodging but Robert was not having it. When I asked he was very condescending about it. It was a busy check in and he was training ...

Reviewed on Feb 6, 2026

Lodge Of Four Seasons Golf Resort, Marina & Spa
Margaritaville Lake Resort Lake of the Ozarks

Margaritaville Lake Resort Lake of the Ozarks

3 out of 5
494 Tan Tar A Drive Osage Beach MO
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Mar 15 to Mar 16
CA $169
CA $210 total
Mar 15 - Mar 16
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
Amenities

Reviewed on Feb 9, 2026

Margaritaville Lake Resort Lake of the Ozarks
The Resort at Lake of the Ozarks

The Resort at Lake of the Ozarks

3 out of 5
3080 Bagnell Dam Blvd Lake Ozark MO
Fully refundableReserve now, pay when you stay
8/10 Very Good! (568 reviews)
Yes

Reviewed on Feb 8, 2026

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The Resort at Lake of the Ozarks
See all 3,766 properties in Lakeside
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 Lakeside

Paradise Parasail Inc.

Catch an event at Paradise Parasail Inc., and enjoy other activities in Lake Ozark such as boating. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

Paradise Parasail Inc.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.