Lakeside vacation rentals

We found 844 vacation rentals — enter your dates for availability

Select from 44 homes, 21 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?
The most sought-after types of vacation rentals in Lakeside are cottages. Ready for more choices? Vrbo has plenty of options to match our guests’ diverse needs, so you’ll see vacation homes in loads of sizes and shapes. The ideal home away from home is waiting for you — get yours today.
How much does it cost to rent a vacation rental in Lakeside?
Several factors affect how much you’ll pay for a vacation rental in Lakeside, like the type of property, length of stay and season. Still, all our vacation homes have one thing in common — unbeatable value. Simply add your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Lakeside?
Prices for beach houses in Lakeside vary depending on the style and size of the property and when you plan to travel. All you need to do is enter your travel dates into Vrbo and how many guests to view available options and prices. From there you can use our filters to narrow your search by nearby activities, amenities, ratings and more.
Are there pet-friendly vacation rentals in Lakeside?
Good news! Yes. You can pick from 61 vacation rentals that cater to pets in Lakeside. Several of our pet-friendly vacation rentals come with space outdoors for your furry pal to have fun in, special dog beds, complimentary treats and proximity to parks or green space. Apply the “Pets allowed” filter to find a vacation home on Vrbo that’s pawfect.
Can I rent a house with a pool in Lakeside?
Add an extra layer of fun to your trip by booking your crew into one of the 10 houses with a private pool in Lakeside. Use our handy search filter to find the kind of property you want on Vrbo, and then spend lazy days splashing around in a swimming pool that’s all your own.
What are popular rental amenities in Lakeside?
Some of the most popular rental amenities people prefer in Lakeside include a sauna, a firepit and an electric car charging station. Whether you’re vacationing with family, your besties or even pets, Vrbo vacation homes provide the best amenities for chilling out with the people you cherish the most.
Are there large group vacation rentals in Lakeside?
You can choose from 25 vacation properties in Lakeside that can accommodate a group of 10 or more people. Whether you’re planning a family trip or a celebration like a birthday, there’s plenty of space to get your favorite people together under one roof.
Are there vacation rentals in Lakeside that welcome kids?
Lakeside has 61 family-friendly vacation rentals. And finding a stay that welcomes youngsters is simple with Vrbo’s “Properties good for families” filter. As well as having the whole place to yourselves, you’ll have access to amenities and perks such as bunk beds, kitchens and yards.
What are the top attractions for families in Lakeside?
If you’re seeking some fun for the whole family near the center of Lakeside, plan a visit to Burnison Galleries.
Can I find two-bedroom vacation rentals in Lakeside?
Lakeside has 12 two-bedroom properties for you to select from. Go for a vacation home with all the comfort and space you’re looking for at an attractive price on Vrbo.
Are there vacation rentals with WiFi in Lakeside?
You’ll have a choice of 19 vacation rentals with WiFi in Lakeside. If you’d like to disconnect from daily life on your escape, but still need to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Lakeside?
Select your travel dates and then use our filters to see vacation rentals with air conditioning in Lakeside on Vrbo. With 60 air-conditioned properties available, you can enjoy a cool and comfy break.
How old do you have to be to rent a vacation rental in Lakeside?
You should check with the Lakeside vacation home you want on Vrbo as age restrictions differ. However, generally it’s 16, 18 or 21.
How long can I rent a vacation rental in Lakeside for?
It all depends on the Lakeside property. To view all available options offering extended stays, just enter your travel dates and number of people into Vrbo. You can enjoy having the whole place to yourself, as well as amenities such as air conditioning, a kitchen and an outdoor space where your little ones can play. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.
Does Vrbo offer discounts for vacation homes in Lakeside?
On Vrbo, we’ve got some incredible discounts and bargains for Lakeside. Browse our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re planning a mini vacay or a much longer stay, Vrbo has lots of options for every budget and style.

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