Lakeside Vacation Rentals

Compare 10 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

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Lakeside vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
The Gatehouse on Orchard Beach
3 Bed | 2 Bath | Sleeps 8

The Gatehouse on Orchard Beach - Lakeside, MI

$868 avg / night
(excludes fees and taxes)
4.57 (23)
Friendly Farms
3 Bed | 3.5 Bath | Sleeps 6

Friendly Farms - Lakeside, MI

$704 avg / night
(excludes fees and taxes)
4.76 (21)
Lake Michigan Adventures
2 Bed | 1.5 Bath | Sleeps 4

Lake Michigan Adventures - Lakeside, MI

$361 avg / night
(excludes fees and taxes)
4.26 (19)
Turner Cottage
3 Bed | 2 Bath | Sleeps 8

Turner Cottage - Lakeside, MI

$395 avg / night
(excludes fees and taxes)
4.65 (23)
Four Seasons Retreat
3 Bed | 2 Bath | Sleeps 6

Four Seasons Retreat - Lakeside, MI

$597 avg / night
(excludes fees and taxes)
4.67 (12)

View 5 more homes

Recent Lakeside vacation rental reviews

Clean, had everything we needed.
Debbie H. | May 2025
Incredible space for a getaway. Beautifully appointed home on a secluded and nature-filled lot. Some noise pollution from nearby train. Overall I would book again.
Charlotte S. | Apr 2025
One word….magic. Can’t say enough great things about The Gatehouse. We keep coming back for the peace and tranquility. Clean, simple, comfortable. Beach and cabana are the best!
Carmen T. | Apr 2025
Lakeside Frequently Asked Questions

Yes, 25 of our Lakeside homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 73 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!