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


House rentals

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Lakeside vacation rentals for every getaway

Dog-friendly Hot tub Internet
Friendly Farms
3 Bed | 3.5 Bath | Sleeps 6

Friendly Farms - Lakeside, MI

$687 avg / night
Turner Cottage
3 Bed | 2 Bath | Sleeps 8

Turner Cottage - Lakeside, MI

$493 avg / night
The Gatehouse on Orchard Beach
3 Bed | 2 Bath | Sleeps 8

The Gatehouse on Orchard Beach - Lakeside, MI

$756 avg / night
Sunset Breeze
4 Bed | 3 Bath | Sleeps 10

Sunset Breeze - Lakeside, MI

$624 avg / night
Four Seasons Retreat
3 Bed | 2 Bath | Sleeps 6

Four Seasons Retreat - Lakeside, MI

$459 avg / night

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Recent Lakeside vacation rental reviews

We LOVED staying at the Gatehouse! It’s beautifully detailed with views of Lake Michigan. Can’t beat the short walk down to the beach! We walked for miles everyday and had gorgeous sunsets over the water. Orchard Beach is private and quiet. The people you come across are all very friendly. Another treat was to have a bonfire on the beach and sit in the private beach cabana, sheltered from the wind by a dune. Just Stunning. Can’t wait to return !
Carmen T. | Jan 2024
I stayed at The Gatehouse for a (much needed) solo pre-holiday get away. Everything was just perfect. The home has everything you need to relax, refresh, and recharge. The beach was impeccable, & the cabana was the perfect place to meditate for a bit. The home is fully stocked, SUPER clean, and the living room couch is unbelievably comfortable--I may have "accidentally" fallen asleep while reading on that couch! =) This stay was exactly what I needed to get ready for the holiday hustle & bustle. 10/10 recommend.
Kristen S. | Nov 2023
We loved this little house. We loved the access to the beach and the little shack was perfect for hanging out. House was very quiet and comfortable. Not ideal for large groups though. No indoor dining area. Not enough cups for 8 people even though the house sleeps 8. And the kitchen is not stocked well. It was extremely difficult to cook for 8 people with one medium sized pot. Also not enough towels or dishwasher fluid.
Joe S. | Oct 2023
Lakeside Frequently Asked Questions

Yes, 26 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. 87 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!