Lakeside Vacation Rentals

Compare 9 vacation rentals. Enter your trip dates to get started.
USA > Michigan > Lakeside

Make Lakeside your next getaway—choose from 9 great vacation rentals

Explore our Lakeside, MI vacation rentals & cabins

Explore Lakeside house rentals, and more


House rentals

View 9 House rentals

Lakeside vacation rentals for every getaway

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

Friendly Farms - Lakeside, MI

$516 avg / night
Four Seasons Retreat
3 Bedroom | 2 Bath | Sleeps 6

Four Seasons Retreat - Lakeside, MI

$545 avg / night
The Gatehouse on Orchard Beach
3 Bedroom | 2 Bath | Sleeps 8

The Gatehouse on Orchard Beach - Lakeside, MI

$682 avg / night
Lake Michigan Adventures
2 Bedroom | 1.5 Bath | Sleeps 6 (4 Adults Max)

Lake Michigan Adventures - Lakeside, MI

$309 avg / night
Hygge House
2 Bedroom | 2 Bath | Sleeps 6

Hygge House - Lakeside, MI

$359 avg / night

View 4 more homes

Recent Lakeside vacation rental reviews

Mitchell H. | Sep 2022
Have stayed in winter & summer & this home lives up to its “cozy” name. Looking forward to another stay any time of year. Love the fireplace in the winter months & the large backyard in the warmer ones. The photos on the listing don’t lie what’s in & out of the home.
Carolyn M. | Sep 2022
A belated review but our family of five loved our stay at Friendly Farms! The fire pit and s’mores were a huge hit- the hot tub may have been an even bigger hit. Everything was cozy and comfortable and the location to local spots, beaches and more was great. We’ve already told friends about it and hope to come back again sometime!
Caitlin M. | Sep 2022
Lakeside Frequently Asked Questions

Yes, 31 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. 112 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!