Lakeside Vacations from $314

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon
    Better together
    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Lakeside Vacation

With a Lakeside vacation package, say goodbye to travel planning and hello to an effortless adventure. Every detail of your journey has been taken care of before you depart, so you can make the most of your time discovering this exciting city. Fill your schedule with tours of Four Winds Casino New Buffalo, New Buffalo Public Beach and Warren Dunes State Park Beach, some of the attractions you shouldn't miss during a trip to Lakeside. Browse Expedia's wide range of travel options and start planning your dream vacation to Lakeside today.

The Latest Lakeside vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG
Palmer House a Hilton Hotel
LondonHouse Chicago, Curio Collection by Hilton
Hotel Felix River North/Magnificent Mile
Hilton Chicago O'Hare Airport
Don't see what you're looking for?
See all available trips from Columbus to Lakeside
View all trips

Discover the most popular places to visit in Lakeside

Lakeside Hotel Deals

Blue Chip Casino Hotel and Spa
Blue Chip Casino Hotel and Spa
3.5 out of 5
777 Blue Chip Drive, Michigan City, IN
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $157 total per night from Jul 7 to Jul 8
$157 total
Jul 7 - Jul 8
Total includes taxes and fees
8/10 Very Good! (1,571 reviews)
"The property was very clean and the staff was professional and nice"

Reviewed on Jun 30, 2025

Blue Chip Casino Hotel and Spa
Four Winds Casino Resort – New Buffalo
Four Winds Casino Resort – New Buffalo
3.5 out of 5
11111 Wilson Road, New Buffalo, MI
$164 nightly
The price is $173 total per night from Jul 31 to Aug 1
$173 total
Jul 31 - Aug 1
Total includes taxes and fees
9.2/10 Wonderful! (1,349 reviews)
"Event was within the property. Lots to do with music/band playing by the pool and close to Lake Michigan."

Reviewed on Jun 30, 2025

Four Winds Casino Resort – New Buffalo
Baymont by Wyndham Michigan City
Baymont by Wyndham Michigan City
2.5 out of 5
4128 South Franklin Street, Michigan City, IN
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $90 total per night from Jul 6 to Jul 7
$90 total
Jul 6 - Jul 7
Total includes taxes and fees
5.6/10 (961 reviews)
Decent Hotel for the Price
"Overall, The Baymont is a decent choice if you’re looking for somewhere reasonably priced and convenient. It’s not a luxury experience by any means, but it’s functional and does the job for a short stay. There are certainly some areas that could be improved, but for the price, it’s not a bad ..."

Reviewed on Jul 2, 2025

Baymont by Wyndham Michigan City
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
Closest Airport
South Bend Intl. Airport (SBN)
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Warren Dunes State Park, Warren Dunes State Park Beach and Michiana Beach

More vacations you might like

Frequently asked questions

How much does a Lakeside vacation package cost?
Offering great value package deals from $314 on Expedia, you'll be pleasantly surprised at how much a vacation to Lakeside costs! Our packages make travel planning easier and save you more.
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're likely to find better prices on flights and accommodations during these months --- perfect for a budget-friendly break.
How many days is enough for Lakeside?
With a well-planned itinerary, you can easily hit the main Lakeside sights in a handful of 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?
Use Expedia's filters to find some great Lakeside package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Lakeside package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Lakeside vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Lakeside vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Lakeside?
Score amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Lakeside break.
Does Expedia offer Book Now, Pay Later Lakeside vacation packages?
Your Lakeside getaway should be an escape from your busy life, not a source of money-related stress. So to allow you a bit more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.