Lakeside Vacations from $305

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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.
HoteLumiere at the Arch - A Caesars Rewards Destination

HoteLumiere at the Arch - A Caesars Rewards Destination

4 out of 5
Downtown St. Louis
Price was $412, price is now $305 per person
$305
per person
Jan 29 - Jan 31
found 18 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to St. Louis (STL)
13.2/10 Exceptional! (1,001 reviews)
Very nice and convenient location

Reviewed on Oct 29, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $767, price is now $507 per person
$507
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
18.4/10 Exceptional! (1,600 reviews)
Very comfortable and clean. Charming place with character

Reviewed on Nov 18, 2025

Westgate Branson Lakes Resort

Westgate Branson Lakes Resort

4 out of 5
Price was $838, price is now $624 per person
$624
per person
Jan 12 - Jan 16
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (SGF)
16.4/10 Exceptional! (849 reviews)
Was way more than we expected at a great price!!

Reviewed on Nov 17, 2025

Days Inn by Wyndham Branson Ozarks

Days Inn by Wyndham Branson Ozarks

2 out of 5
Branson Meadows
Price was $750, price is now $561 per person
$561
per person
Jan 12 - Jan 16
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (SGF)
17.2/10 Exceptional! (456 reviews)
Yes to both but I asked for no stairs. I had lots of stair, which confined me to the room. I have knee and leg problems. I can't do stairs. So while my family was out enjoying the city. I had to stay behind and play on my phone.

Reviewed on Nov 14, 2025

Stormy Point Village Resort

Stormy Point Village Resort

4 out of 5
Price was $925, price is now $702 per person
$702
per person
Jan 12 - Jan 16
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (SGF)
17.6/10 Exceptional! (1,035 reviews)
This was the perfect fit for our family!

Reviewed on Nov 16, 2025

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Discover the most popular places to visit in Lakeside

Bagnell Dam

4/5(176 reviews)

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

Willmore Lodge

4/5(26 reviews)

Take the family on an outing to Willmore Lodge during your trip to Lake Ozark. Wander the area's lakeside or simply enjoy one of its lively bars.

Willmore Lodge

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
$90 nightly
The price is $99 total per night from Nov 20 to Nov 21
$99 total
Nov 20 - Nov 21
Total with taxes and fees
7.2/10 Good! (1,071 reviews)
This resort had amazing staff members. It was a very clean environment. Our room had a beautiful view of the lake. We can’t wait to stay again and check out their Christmas events!

Reviewed on Nov 17, 2025

Lodge Of Four Seasons Golf Resort, Marina & Spa
Days Inn by Wyndham Osage Beach Lake of the Ozarks

Days Inn by Wyndham Osage Beach Lake of the Ozarks

2 out of 5
4755 Osage Beach Parkway Osage Beach MO
Fully refundableReserve now, pay when you stay
$61 nightly
The price is $66 total per night from Dec 1 to Dec 2
$66 total
Dec 1 - Dec 2
Total with taxes and fees
7/10 Good! (1,000 reviews)
All is good

Reviewed on Nov 11, 2025

Days Inn by Wyndham Osage Beach Lake of the Ozarks
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
$126 nightly
The price is $135 total per night from Dec 2 to Dec 3
$135 total
Dec 2 - Dec 3
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
We have the best time at MV! The staff were amazing especially Chyeal

Reviewed on Nov 13, 2025

Margaritaville Lake Resort Lake of the Ozarks
See all 3,827 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.

Find the Best Lakeside Vacation Packages

Lakeside Essential Information

Language
English
Currency
U.S dollars
Top Sights
Lake of the Ozarks and Bagnell Dam Viewpoint, Osage National Golf Club and The Ridge Golf Course

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Frequently asked questions

How much does a Lakeside vacation package cost?
Offering great value package deals from $305 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.