Lakeside Vacations from $359

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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.

The Latest Lakeside vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton St. Louis Airport

Hilton St. Louis Airport

3.5 out of 5
Woodson Terrace
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
7.6/10 Good! (1,006 reviews)
Nothing exciting, no options for food except restaurant on site. Need car to eat elsewhere. I want to recognize Rowanda from housekeeping who was able to get me a functional coffee machine the last day. There are other hotels nearby to consider next time.

Reviewed on Aug 4, 2025

White House at Grand Central

White House at Grand Central

4 out of 5
Grand Center
per person
Oct 23 - Oct 27
found 2 hours ago
Roundtrip flight included
New York (JFK) to St. Louis (STL)
8.6/10 Excellent! (114 reviews)
It was very clean and nicely decorated. The house is a cool old building. The AC worked great (important, as it was super muggy outside.) I was only there for a couple nights but I think it would have worked well for a longer stay.

Reviewed on Jul 9, 2025

Greenstay Hotel & Suites

Greenstay Hotel & Suites

2.5 out of 5
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (SGF)
8.6/10 Excellent! (1,478 reviews)
We stayed here one night. Checked in late. No other guests at the desk when I walked in. Wasnt greeted when I walked in. Got to the counter and I thought the lady behind the desk was finishing up a task so I approached and stood there. When I looked at her, she was just staring at me like “what do you want”. Still no greeting. So I then said “Oh, checking in”. So already I’m not pressed. The room was fine for one night. Mattresses are old and need to be replaced.

Reviewed on Aug 7, 2025

Hilton Garden Inn St. Louis/O'Fallon MO

Hilton Garden Inn St. Louis/O'Fallon MO

3 out of 5
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.8/10 Excellent! (692 reviews)
The food in the restaurant was terrable. I had the meat balls and I could not eat them

Reviewed on Jun 30, 2025

Hampton Inn By Hilton St Louis Airport

Hampton Inn By Hilton St Louis Airport

2.5 out of 5
Woodson Terrace
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.2/10 Very Good! (40 reviews)
Easy airport access, parking, dining and you may catch some live music next door.

Reviewed on Aug 10, 2025

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Discover the most popular places to visit in Lakeside

Bagnell Dam

You can find out about the history of Lakeside with a trip to Bagnell Dam. Amble around this family-friendly area's lakeside and enjoy its lively bars.

Bagnell Dam

Lake of the Ozarks and Bagnell Dam Viewpoint

Learn about the local history of Lakeside when you spend time at Lake of the Ozarks and Bagnell Dam Viewpoint. While you're in the area, wander around the natural setting.

Lake of the Ozarks and Bagnell Dam Viewpoint

Osage National Golf Club

Play a round of golf at Osage National Golf Club and enjoy other activities in Lake Ozark such as boating. Wander the lakeside in this family-friendly area.

Osage National Golf Club

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
$122 nightly
The price is $132 total per night from Sep 7 to Sep 8
$132 total
Sep 7 - Sep 8
Total includes taxes and fees
7/10 Good! (1,001 reviews)
Weekend getaway
"The hotel is clean, but definitely dated. Fun quarky things about it :) we enjoyed our stay. The bed was super comfy. We only were able to see 2 restaurants open… the HK one was not our favorite, it was pricey and frozen food :/ The food we had at the pool (nachos) were pretty good. HUGE portion ..."

Reviewed on Aug 4, 2025

Lodge Of Four Seasons Golf Resort, Marina & Spa
Inn at Grand Glaize

Inn at Grand Glaize

2 out of 5
5142 Osage Beach Pkwy, Osage Beach, MO
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $91 total per night from Aug 11 to Aug 12
$91 total
Aug 11 - Aug 12
Total includes taxes and fees
7.2/10 Good! (192 reviews)
"Two thumbs up"

Reviewed on Aug 1, 2025

Inn at Grand Glaize
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
$166 nightly
The price is $178 total per night from Sep 8 to Sep 9
$178 total
Sep 8 - Sep 9
Total includes taxes and fees
8.2/10 Very Good! (1,003 reviews)
"We loved staying at this resort! It has everything you need and the staff is very friendly and helpful! We will be back again soon!"

Reviewed on Jul 31, 2025

Margaritaville Lake Resort Lake of the Ozarks
See all 3,749 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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Frequently asked questions

How much does a Lakeside vacation package cost?
Offering great value package deals from $359 on Expedia, you'll be thrilled with how little a vacation to Lakeside costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Lakeside?
If you'd like to score a cheap Lakeside vacation package, consider planning a trip in November, December and January. You'll generally find better prices on flights and accommodations during these quieter months — ideal for a budget-friendly break.
How many days is enough for Lakeside?
With a well-planned schedule, you can easily hit the main Lakeside attractions in a few days. But if you prefer to explore off the beaten track or go on day tours, think about booking your Lakeside vacation for longer.
How to find the best Lakeside package deals?
Finding a cheap Lakeside package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, add a few filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most economical Lakeside package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Lakeside vacation as a package?
You can enjoy significant savings on your Lakeside break by booking a personalized vacation package. Check the "Package" heading, then enter your destination and travel dates to see some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Lakeside?
Score incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Lakeside trip.
Does Expedia offer Book Now, Pay Later Lakeside vacation packages?
If you're like us, you love discovering new places but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Lakeside vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.