Lakeside Vacations

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Find the Best Lakeside Vacation Packages

Lakeside Hotel Deals

1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More

1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More

Lakeside MI
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1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location

Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location

Lakeside MI
10/10 Exceptional! (152 reviews)
"This was a beautiful property. It truly is unique and one of a kind. I would like to go back in the summer and enjoy the screened in cottage a little bit more. The area is beautiful, and we went at the perfect time of year to see all the leaves change, the weather was outstanding. Truly everything ..."

Reviewed on 6 November 2026

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Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location
Four Winds Casino Resort ā€“ New Buffalo

Four Winds Casino Resort ā€“ New Buffalo

3.5 out of 5
11111 Wilson Road New Buffalo MI
Fully refundableReserve now, pay when you stay
The price is AEDĀ 327 per night from Nov 16 to Nov 17
AEDĀ 327
AEDĀ 380 total
16 Nov - 17 Nov
includes taxes & fees
Four Winds Casino Resort ā€“ New Buffalo
See all 1,911 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.

Stay near popular Lakeside attractions

Burnison Galleries

Burnison Galleries showcases diverse works from regional artists in a welcoming Lakeside setting. Browse the curated collection at your leisure, with no admission fee required for this cultural Michigan experience.
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Frequently asked questions

How much does a Lakeside vacation package cost?
You'll find cheap prices 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 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?

  1. Pick the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to visit Lakeside.
  2. 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.
  3. 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.
  4. 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.