Discover a selection of 500 vacation rentals in Lakeside that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $186 per night, and houses and cabins are popular options for a stay in Lakeside. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Lakeside
Destination guide

Enjoy the small-town retreat of Lakeside

For a weekend of relaxation, take a trip to the small beachfront community of Lakeside. Located on the shores of Lake Michigan, the town is just a stone’s throw away from the thriving metropolis of Chicago. Visitors come here to experience the crystal waters and restful quiet that Lakeside vacation rentals can offer. Much of the Lakeside beach access is private, meaning you won’t have to deal with an overload of people while working on your tan. If you’re looking for more than some fun in the sun, you can also check out the area’s nearby wineries.

Things to do

Relaxation reigns supreme in Lakeside

While chilling on the beach is the main attraction of Lakeside vacation rentals, the area also has several wineries. On the outskirts of town is St. Julian Winery, which offers a variety of ciders, red wines, white wines, and spirits. Also nearby is Round Barn, a winery, distillery, and brewery that lets you sample up to six wines or spirits at a time. Other activities near Lakeside include teeing off for a round of golf at the Chikaming Country Club or taking a gamble at Four Winds Casino.


Quiet beaches and quaint shops in Lakeside

There are plenty of activities in Lakeside to keep you happy, whether you’re on a romantic couple’s getaway or a large family vacation. Many people prefer to simply lounge on the area’s private beaches, enjoying the sun or cooling off in the water. The water is also great for fishing, boating, and kayaking if you get tired of taking it easy. Water not your thing? Skip the beaches and head Downtown to experience Lakeside shopping. You’ll be able to hit up antique stores and other small, country shops.


Savor your days in the sun at Lakeside

A typical Lakeside weather forecast in the summer is bright and warm, with average temperatures in July reaching around 80 degrees. Because of this, if swimming and water sports are your game, you’ll want to search for Lakeside vacation rentals in June through August. Late spring and early fall can be just as pleasant without quite as much heat, with average highs in April and October reaching the 60s. Visiting during these times is a great option if you just want to lounge on the beach without getting wet.

Natural features

Beaches, birding, and parks in Lakeside

With acres of waterfront surrounded by lush green trees, Lakeside is an idyllic paradise for those craving relaxation. Terrain is mostly flat and easily walkable by foot, meaning you can leave the car parked. While most of the Lakeside beaches are private, you can access public beaches at nearby New Buffalo and Warren Dunes State Park. Warren Dunes State Park also features a number of waterfront hikes spread out over an expanse of 1,952 acres. Bird lovers staying in Lakeside can rejoice, as there are 353 different bird species throughout the entire Harbor County area to observe.

How to get there

Transportation options to and around Lakeside

Fly into South Bend, IN (SBN-South Bend Intl.), the closest airport, located 21.1 mi (33.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Chicago, IL (MDW-Midway Intl.), which is 55.6 mi (89.5 km) away.

How many vacation rentals are available around Lakeside?

Our 2021 property listings offer a large selection of 625 vacation rentals around Lakeside. From 582 house rentals to 124 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.