Name: 1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Rating: 9.2

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.

Kinzie Hotel

Downtown Chicago

CA $1,158

per person

May 8 - May 13

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (2,091 reviews)

Clean room and great staff!

Reviewed on Mar 24, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,451

per person

Jun 4 - Jun 8

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (3,495 reviews)

The rooftop wasn’t open, everything else was great

Reviewed on Mar 24, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,510

per person

Jun 4 - Jun 8

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (2,401 reviews)

I love everything!! It was a beautiful experience. Second time staying.

Reviewed on Mar 24, 2026

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

CA $1,474

per person

Jun 4 - Jun 8

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (1,021 reviews)

I would have rated all 5 star but the restaurant Atwood was closed and we weren’t notified in time to change plans! The staff and (Mr.Brown ) were extremely accommodating! It was my bday and they decorated our room with all sorts of goodies including a hand made stuffed wash cloth doggie! Our housekeeper was amazing too! The room decor is such fun and extremely clean! The only drawback is the rooms are very small and some not configured well! All and all it’s a wonderful place to experience!!!!🍍

Reviewed on Mar 18, 2026

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Lakeside Hotel Deals

Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location

Lakeside MI

10/10 Exceptional! (138 reviews)

Great place. Beautiful home and perfect location to New Buffalo, Lakeside, and other places. The owner was very responsive and helpful. Strongly recommend this home.

Reviewed on Nov 9, 2025

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Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!

Lakeside MI

9/10 Wonderful! (50 reviews)

Really liked the layout, the added privacy of the studio was great though it could use a microwave, table or desk and a place to put clothes. The beach is great and the kayaks are a great added bonus.

Reviewed on Sep 25, 2025

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

Lakeside MI

9.2/10 Wonderful! (66 reviews)

Great property. Just as advertised. Hope to come back soon

Reviewed on Sep 26, 2025

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See all 1,829 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.