Lakeside Vacation Rentals

Compare 8 vacation rentals.
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Make Lakeside your next getaway

Explore our Lakeside, MI vacation rentals & cabins

Explore Lakeside house rentals, and more

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House rentals

View 8 House rentals

Lakeside vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Lakeshore Haven
3 Bed | 2 Bath | Sleeps 8

Lakeshore Haven - Lakeside, MI

$352 avg / night
(excludes fees and taxes)
4.5 (2)
The Gatehouse on Orchard Beach
3 Bed | 2 Bath | Sleeps 8

The Gatehouse on Orchard Beach - Lakeside, MI

$705 avg / night
(excludes fees and taxes)
4.46 (26)
Painted Porch Cottage
2 Bed | 1 Bath | Sleeps 4

Painted Porch Cottage - Lakeside, MI

$293 avg / night
(excludes fees and taxes)
4.0 (6)
Friendly Farms
3 Bed | 3.5 Bath | Sleeps 6

Friendly Farms - Lakeside, MI

$476 avg / night
(excludes fees and taxes)
4.78 (23)
Lakeside Living
2 Bed | 1 Bath | Sleeps 4

Lakeside Living - Lakeside, MI

$176 avg / night
(excludes fees and taxes)
4.56 (9)

View 3 more homes

Recent Lakeside vacation rental reviews

Perfect sized home. Great parking. Awesome screen porch. Great to have a washer and dryer. Tons of kitchen item options. Beds are firm.
Troy N. | Oct 2025
Appears this house has been recently remodeled. Great location on Lake shore right across from the entrance to the beach. Everything you need is in the house. Bring k-cups for the coffee machine. Would definitely return.
William G. | Oct 2025
Very close to the designated private beach. Clean, old-school cottage with charm. Very close to Red Arrow Highway, so you have a very short drive to all the nearby restaurants & local attractions. Seamless check-in process, good value overall.
Robert H. | Oct 2025
Lakeside Frequently Asked Questions

Yes. 65 of our Lakeside vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Lakeside vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Lakeside team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Lakeside, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Situated on the shores of Lake Michigan, the aptly named Lakeside offers comfortable and family-friendly accommodations in a cozy waterfront community. Our Lakeside, MI vacation rentals are the perfect spot to bring your family, and with St. Joseph about a thirty-minute drive north, you’ll never be short on things to do. Pier Street Beach, a public access beach, sits right in the middle of Lakeside, making it an ideal spot for fun in the sun. Outdoors enthusiasts will love exploring Grand Mere State Park, a bit north of town, and Warren Dunes State Park. Whether you’re traveling from Chicago or somewhere else, you’ll find yourself refreshed by a stay in one of our Lakeside, MI cabin rentals or vacation homes. Book today!