Lakeside vacation rentals

We found 859 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Select from 47 homes, 23 cottages, and other vacation rentals in Lakeside to find one that's perfect for your trip. Vacation rentals provide the amenities you need and want for your family, friends, or furry companion, like WiFi and cable TV. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

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Head to the historic city of Lakeside

The area's architecture and history are just a few of the reasons to vacation in Lakeside. This city's lake, beaches and forests draw many visitors. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

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.

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.

Traveling to and around Lakeside

Fly into South Bend Intl. Airport (SBN), the closest airport, located 21 mi (33.8 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Chicago Midway Airport (MDW), which is 55.4 mi (89.2 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Lakeside?

Houses are the most popular style of vacation rental in Lakeside, according to our data. Even if you've got something else in mind, Vrbo has properties in all shapes and sizes. Filter our options to find your ideal match.

How much does it cost to rent a vacation rental in Lakeside?

A range of things can determine the price of a vacation rental in Lakeside, including the season, type of property and length of stay. Still, all our vacation homes have something in common — excellent value. Simply add your travel dates to find your perfect match.

How much does it cost to rent a beach house in Lakeside?

Prices for beach houses in Lakeside may differ depending on the style and size of the property and time of year you're traveling. Simply enter your travel dates into Vrbo and the number of guests to view your vacation rental options and prices. From there you can use the filters to tailor your search by ratings, nearby activities, amenities and more.

Are there pet-friendly vacation rentals in Lakeside?

With 62 properties that host four-legged guests, your furry buddy can join in on your Lakeside getaway. Use the filter tool to search our pet-friendly vacation rentals and find your pawfect vacation home on Vrbo.

Can I rent a house with a pool in Lakeside?

Add an extra layer of fun to your getaway by booking your group into one of the 12 houses with a private pool in Lakeside. Use our search filter to find properties with pools on Vrbo, then spend your days playing and splashing in a swimming pool that's only for you.

What are popular rental amenities in Lakeside?

A firepit, a beach view and an electric car charging station top the list of most popular rental amenities in Lakeside. Whether you plan to travel solo, with a partner or as a family group, Vrbo will help you find a vacation rental that suits your style with all the options you need.

Are there large group vacation rentals in Lakeside?

Lakeside has 27 vacation homes that can accommodate 10 or more guests. These properties come with all the space you need to share good times with family and friends.

Are there vacation rentals in Lakeside that welcome kids?

With 62 family-friendly vacation rentals available in Lakeside, now is an awesome time to introduce the little ones to the thrills of travel. Just click on our "Properties good for families" filter box to find stays that feature conveniences perfect for vacationing families, like extra bedrooms, backyards, bunk beds and entertainment areas.

What are the top attractions for families in Lakeside?

Keep your kids entertained at these fantastic family-friendly attractions in Lakeside:

  • New Buffalo Public Beach
  • Michiana Beach
  • Cherry Beach

Can I find two-bedroom vacation rentals in Lakeside?

Take your pick of 12 two-bedroom vacation properties in Lakeside. Settle the kids into the second room or maybe fill it with a couple of your best friends. There's enough space for whoever's fortunate enough to be joining your adventure.

Are there vacation rentals with WiFi in Lakeside?

You can choose from 17 vacation rentals with WiFi in Lakeside. If you want to disconnect from daily life on your vacation, but still want to be connected to the internet, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Lakeside?

You'll have a choice of 60 Vrbo vacation homes with air conditioning in Lakeside giving you that cooling breeze and extra bit of comfort. Simply enter your desired travel dates and then take advantage of our filter tool to help you book properties with air conditioning.

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