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*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Top Lakeside Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
CA $1,257
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
Great stay in an elegant mostly residential building. Smooth check in, but had to fill out a few forms. Very nice staff. Young building with lots of dogs yay!
Reviewed on Sep 24, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,348
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,681 reviews)
Clean room, helpful, friendly staff. Plenty of eats and shopping & things to do for kids.
Reviewed on Sep 24, 2026
Ready to book your vacation to Lakeside?
Lakeside Hotel Deals
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Lakeside MI
9.2/10 Wonderful! (70 reviews)
"Great location and wonderful property. The amenities were great. We visit this area annually and this is my favorite."
Reviewed on Sep 13, 2026
Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location
Lakeside MI
10/10 Exceptional! (149 reviews)
"What a lovely cottage! We felt at home right away. The gardens around the house added to the character and charm. Great decor throughout. We would love to stay here again should we return to the area."
Reviewed on Sep 22, 2026
Four Winds Casino Resort – New Buffalo
11111 Wilson Road New Buffalo MI
Fully refundableReserve now, pay when you stay
CA $125
CA $145 total
Sep 29 - Sep 30
includes taxes & fees
9.4/10 Exceptional! (2,210 reviews)
"I had a wonderful stay! The room was exceptionally clean, comfortable, and inviting, and I really appreciated how thoughtfully the amenities were provided. The staff was friendly, welcoming, and attentive throughout my stay, which made the experience even better. Everything felt well cared for, and ..."
Reviewed on Sep 24, 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 $1,137 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.
Explore a world of travel with Expedia
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- Lovely recently Built NB Home
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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.
