Lakeside Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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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.
Top Lakeside Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,856
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Family friendly, beautiful views. Easy public transportation available.
Reviewed on Aug 7, 2026
Holiday Inn Chicago O'Hare – Rosemont by IHG
CA $1,063
per person
Oct 2 - Oct 6
just found
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,097 reviews)
The front desk staff were exceptional and went above and beyond to make our stay comfortable. They were friendly, attentive, and always willing to help. Their excellent service and warm hospitality truly made a difference. Highly recommended!
Reviewed on Aug 7, 2026
Ready to book your vacation to Lakeside?
Lakeside Hotel Deals
Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location
Lakeside MI
10/10 Exceptional! (145 reviews)
"We had such a wonderful week at your home! The house had everything we needed and more. My kids had a magical time exploring the home, the cool yard, and the unique screened in summer home. We hope to be back in the future! Thank you for the core memories!"
Reviewed on Aug 1, 2026
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Lakeside MI
9.4/10 Exceptional! (68 reviews)
"Great place to stay - especially for a large family or friend group. Steps from the beach. Outstanding communication from property owner."
Reviewed on Jun 16, 2026
Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
Lakeside MI
9/10 Wonderful! (52 reviews)
"Host was very quick to respond & helpful. Beach was gorgeous! Home was very clean. The grill & fireplace were a great bonus for fun. Shops & restaurants in walking distance on a nice trail."
Reviewed on Jul 28, 2026
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.
Stay near popular Lakeside attractions
Eleanor O'Connor Wilson Woods Preserve
You can take time to visit Eleanor O'Connor Wilson Woods Preserve during your travels to Lakeside. Stroll along the lakeside or discover the area's sunsets.
Burnison Galleries
You can spend time studying the exhibits at Burnison Galleries in Lakeside. Stroll along the beautiful beaches or visit the casinos in this romantic area.
Frequently asked questions
How much does a Lakeside vacation package cost?
You'll find cheap prices from CA $809 on Expedia for your Lakeside getaway. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Lakeside costs.
What are the cheapest months to go to Lakeside?
Plan your trip for the off-peak season and you're likely to get cheap Lakeside vacation packages. Bear in mind that public holidays and major local events can impact prices, so do a little research before booking.
How many days is enough for Lakeside?
Lakeside vacations come in many shapes and sizes, but to get a true feel for this destination, we think 3 days is a good ballpark. In this timeframe, you can fit in major attractions like Warren Dunes State Park Beach and New Buffalo Public Beach and track down some underrated spots. Don't miss out on neighbourhoods such as Gordon Beach and Harbert either. If you're smart with your time, you may even be able to take a day trip outside of Lakeside too.
How to find the best Lakeside package deals?
Use Expedia's filter tool to find some tempting Lakeside package deals. When you begin 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 trip for midweek, or search for Lakeside package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Lakeside vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component individually. And you'll still get the freedom to create a tailored Lakeside vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Lakeside?
If you have your Lakeside travel dates confirmed, book as early as you can to grab some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Lakeside?
- Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to visit Lakeside.
- Set a budget: Factor in expenses like flights, transportation and food when working out how much to put aside for your trip to Lakeside. Then, choose a property that suits your budget, whether that's a wallet-friendly option or a high-end retreat.
- Work out your trip length: Consider how much time you want to spend exploring Lakeside. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
- Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Lakeside vacation package that brings all your bookings together.
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- Two separate updated secluded cottages for one price. near beach & restaurants
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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.
