Lakeside Vacations from $275

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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.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $456, price is now $275 per person
$275
per person
Jul 11 - Jul 13
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,649 reviews)
Nice property in the St. Louis area! Very clean and luxurious feel to it. Very safe area as it is up in the mountains and away from the city, police department is even next door. Everything is in walking distance. Our room had a very comfortable king size bed, a couch, nice chair with foot stool, desk with computer chair, fridge and small microwave. The continental breakfast even had Jimmy Dean sausage, egg and cheese biscuits. We were only there one night so we didn't get to enjoy any of the onsite amenities. It is rated as a destination and venue for weddings, etc.

Reviewed on May 17, 2026

Westgate Branson Lakes Resort

Westgate Branson Lakes Resort

4 out of 5
Save 100% on your flight
Price was $1,919, price is now $932 per person
$932
per person
Jul 26 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (SGF)
8.4/10 Very Good! (942 reviews)
My wife loves water views...I chose the Villa with a lake view. The unit was modern and fulfilled our needs. We were close to Branson (15 minutes) so it was convenient to get anywhere. It would be easy to rate it 5 stars, but I deducted a star because they use the cheapest tissue products available. You will probably want to bring your own. Other than that, you'll really enjoy it.

Reviewed on May 20, 2026

Westgate Branson Woods Resort and Cabins

Westgate Branson Woods Resort and Cabins

3.5 out of 5
Shepherd of the Hills
Save 100% on your flight
Price was $1,617, price is now $842 per person
$842
per person
Jul 26 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (SGF)
8.4/10 Very Good! (1,032 reviews)
Didn't like that the room was on an upper floor, 16 steps up and down every time you left the room. Amenities in room were excellent

Reviewed on May 21, 2026

Residence Inn by Marriott St Louis Downtown

Residence Inn by Marriott St Louis Downtown

3 out of 5
Midtown
Price was $908, price is now $638 per person
$638
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to St. Louis (STL)
7.8/10 Good! (1,001 reviews)
Suite was well stocked with utensils etc. The room was clean. Staff was nice. Pool was small and our bathroom door in our room didn’t latch, which was tough with 2 toddlers waddling about.

Reviewed on May 20, 2026

Rock Lane Resort & Marina

Rock Lane Resort & Marina

4 out of 5
Price was $1,431, price is now $1,099 per person
$1,099
per person
Jul 26 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (SGF)
7/10 Good! (70 reviews)
Beautiful view from room, clean room and excellent price. Will recommend to friends

Reviewed on Apr 24, 2026

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Discover the most popular places to visit in Lakeside

Lake of the Ozarks

Bagnell Dam

4/5(178 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
綺麗なゴルフ場

The Cove Golf Course

Play a round of golf at The Cove Golf Course and enjoy other activities in Village of Four Seasons such as boating. While you're in the area, stroll along the lakeside.

The Cove Golf Course

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

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
$140 nightly
The price is $153 total per night from May 25 to May 26
$153 total
May 25 - May 26
Total with taxes and fees
7.4/10 Good! (1,122 reviews)
"Classic ozark property. Beautiful view. Will definitely stay there again!"

Reviewed on May 17, 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
$219 nightly
The price is $234 total per night from May 25 to May 26
$234 total
May 25 - May 26
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
"The room and service was great. My only complaint is that is very difficult to unload and unload. Both myself and my 3vyear old grandaughter fell in rocks on sidewalks before we could make it to the room. There was nothing to load luggage on. We had 4 kids so it was multiple trips. It is difficult ..."

Reviewed on May 22, 2026

Margaritaville Lake Resort Lake of the Ozarks
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
$70 nightly
The price is $76 total per night from Jun 2 to Jun 3
$76 total
Jun 2 - Jun 3
Total with taxes and fees
7.4/10 Good! (305 reviews)
"Excellent property , i liked the big rooms"

Reviewed on May 21, 2026

Inn at Grand Glaize
See all 4,084 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 $275 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.