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259 Lakeside Holiday Accommodations is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews.
Compare Lakeside holiday accommodations from 6 rental sites including HomeAway, TripAdvisor, and more, from $50 a night.

Lakeside Information

About Lakeside

Located on the shores of Lake Michigan, the town of Lakeside in Berrien Country is part of what is known as Harbor Country, a small area with eight charming towns of Lakeside, New Buffalo, Union Pier, Harbert, Warren Dunes, Sawyer, Three Oaks, and Michiana. Lakeside is known for its lovely scenery and rustic lifestyle, which provide great reasons for a weekend getaway. Lakeside is located in the southwest corner of Michigan and is very close to Chicago. This has made Lakeside a popular destination for Chicago residents since the 1920s. True to its name, Lakeside sits on the shores of Lake Michigan, with slightly warmer weather than Chicago. Visitors can drive to freshwater beaches to build sandcastles or go swimming.

Things to do in Lakeside

If you’re visiting Lakeside in the warmer months of the year, go to the beach! You’ll have a lovely time sitting in the warm sand relaxing or reading, and cooling off with a swim in the lake. Walk around the town center to see the coffee shops and boutiques, or to treat yourself to some ice cream in the afternoon.

Visitors can also take a boat out on the water (weather permitting) and spend the afternoon sailing. If you are interested in exploring the shoreline or are looking for more of an active day, go kayaking along the lake or in one of the nearby rivers. Even in lower temperatures, a walk along the sandy dunes is always a pleasant and relaxing time.

Avid golfers should check out the Chikaming Country Club, a well-maintained 18-hole course that has been open since 1913 and is currently managed by John Phillips, PGA. Once you have played through Chikaming, explore Whittaker Woods Golf Club or Grand Beach Golf Course just a couple of miles south.

Day Trips From Lakeside

For a nearby day trip, tourists have the opportunity to visit the 1,950-acre Warren Dunes State Park. The park is open throughout the entire year and has numerous small paths for walking (bikes are not permitted). In addition to the usual beachside activities, visitors have the freedom to choose to hang-glide in the park, where sand dunes can be as tall as 240 feet.

Finally, visitors can also explore any of the other eight towns of Harbor Country, all of which are along a fifteen-mile stretch on the shores of Lake Michigan. Each town is quaint and full of rustic charm, and most of them are tiny enough for the visitors to see within one day.

Lakeside Accommodations

Lakeside has many different accommodation options including cottages and vacation rentals that make for the perfect big city getaway. Most of these accommodations include top notch amenities such as a hot tub, fireplace, and hammocks. Visitors can also opt for bed and breakfast establishments, inns, and small hotels. Try to stay as close to the lake as possible so that you can watch the magnificent sunset.

Transportation In Lakeside

Visitors to Lakeside will need to bring their own car or rent one from the nearest rental service. Alternatively, biking is a great way to explore the green countryside of Lakeside and Harbor Country. A backroads bikeway system of 20 paved bike trails offers cyclists the option to go on self-guided tours ranging from 5 to 60 miles.

Vacation Rentals in Lakeside

Looking for the perfect vacation rental for your Lakeside getaway?’s got you covered. Whether you’re seeking a vacation home, cabin rental or cottage, Lakeside offers 259 affordable vacation home rentals to choose from, with far more amenities, space and comforts than the average hotel room. Select from 234 properties with high-speed WiFi Internet, 53 full with jacuzzi and pool, and homes complete with outdoor patio, great for entertaining with guests. Whatever your needs, find the perfect home rental that best matches your accommodation style and budget.

For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $25 a month. Save hundreds with affordable vacation rentals on and, in many cases, book directly online so you’re all set to go. Lakeside has 259 gorgeous homes with 79 pet-friendly rentals to choose from, perfect for your dog or cat. Check out our vacation rental listings now to get the latest deals, and book the right vacation home rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with

Search properties from 6 vacation rental sites in Lakeside where the top providers in that area are HomeAway, TripAdvisor, and There are 220 HomeAway rentals, 20 TripAdvisor short term rentals and 7 vacation rentals.