Where to stay around Lakeside?

Our 2018 property listings offer a large selection of 630 vacation rentals near Lakeside. From 419 Houses to 138 Bungalows, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Lakeside for a holiday or a weekend are on HomeAway.

What are the popular points of interest near where I can stay when traveling to Lakeside?

HomeAway offers a large selection of vacation rentals near lovely places in Lakeside. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Indiana Dunes National Lakeshore: 338 vacation rentals
  • Warren Dunes State Park: 620 vacation rentals
  • Sheridan Beach: 853 vacation rentals
  • Blue Chip Casino: 848 vacation rentals
  • Four Winds Casino New Buffalo: 890 vacation rentals

But there are many other points of interest around Lakeside listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Lakeside?

Yes, of course. HomeAway has 419 Houses in Lakeside. Our other popular types of vacation rentals in Lakeside include:

  • Bungalows: 138 rentals available
  • Cottages: 138 rentals available
  • Cabins: 138 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Lakeside?

Yes, you can select your preferred vacation rental with pool among our 183 vacation rentals with pool available in Lakeside. Please use our search bar to access the selection of vacation rentals available.

    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.

    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.

    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.

    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.

    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.