Lakeside Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Lakeside

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! (151 reviews)
"Fun cottage with great character and plenty of room to entertain. Pet friendly and Bill’s communication was top notch. Can’t wait to get back."

Reviewed on 12 Oct 2026

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Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location
Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

3.5 out of 5
11111 Wilson Road New Buffalo MI
Fully refundableReserve now, pay when you stay
The price is €92 per night from 4 Nov to 5 Nov
€92
4 Nov - 5 Nov
includes taxes & fees
Four Winds Casino Resort – New Buffalo
See all 1,900 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 holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Lakeside costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Lakeside?
To pick up cheap Lakeside holiday packages, plan your trip outside of peak periods like public holidays and major festivals. You'll generally find lower prices and better availability when it's less busy.
How many days is enough for Lakeside?
Typically, a handful of days is enough to check out the major attractions during your Lakeside holiday. But if you'd like to have some time to kick back or go on day tours, think about extending your itinerary.
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 holiday package as early as possible.
Is it cheaper to book a Lakeside holiday as a package?
Expedia holiday 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 holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday 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.
How to plan a trip to Lakeside?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Lakeside.
  2. Set your budget: Factor in costs such as flights, food and transportation when calculating how much to set aside for your trip to Lakeside. Then, pick a hotel that fits your budget, whether that's a wallet-friendly stay or a high-end getaway.
  3. Decide your trip length: Think about how long you'd like to spend exploring Lakeside. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick a Lakeside holiday package that brings all your bookings together.

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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.