Discover a selection of 1,000 vacation rentals in Lakeside, MI 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 private pools. Prices start at $205 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

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.

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

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.

What are the top vacation rentals in or near Lakeside?

Whatever you're looking for in a getaway, you'll find a rental property in or around Lakeside that's right up your alley. Why not try these on for size?:

  • "5 Min. Walk To Mckinley St. Beach" is a favorite with guests. Around 2 miles from Lakeside, it has 2 bedrooms and loads of handy amenities, including children's games and a nearby waterfront.
  • Alternatively, make your home away from home at "It's A Dog's Life" - Unleash Your Fun Here". Located around 2 miles from the heart of Lakeside, it has 3 bedrooms and comes with a theme park and golf.

For even more great options, use the search bar at the top of the page to find the perfect Lakeside vacation rental for you.

What are the best tiny house vacation rentals in or near Lakeside?

You need only open the door to our tiny house vacation rentals in Lakeside to figure out that great things really do come in small packages. Ingeniously designed to maximize space, these fun-sized digs promise a big vacation experience:

  • Enjoy a simpler way of life at "Perfect For Two A Little Hideaway In The Woods. Tiny House". Amenities at this gem in Sawyer include heating, internet services and more.
  • "Modern Minimalist Tiny House" comes with plenty of conveniences, such as an electric kettle and a kitchen. Located in Sawyer, you'll be able to live large in this small but cleverly designed hideaway.

What are the top-rated vacation rentals for weekend getaways in or near Lakeside?

Escape the hustle and bustle of everyday life at one of our weekend getaways in or near Lakeside. Whether you'd like to hang out with buddies or spend treasured time with the fam, there'll be something to suit your style. Try these top-rated properties on for size:

  • "Walk To Private Beachfire Pit" is around 2 miles southwest of Lakeside and will be just the thing to refresh your spirit. You'll enjoy the convenient amenities here, including nearby birdwatching activities and winery tours.
  • "Stones Throw' Lakeside Home - Walk To Marina + Town" is another fantastic option to consider. It's located about 6 miles to the southwest of Lakeside and features a firepit, a TV and more.

Can I find studio apartments for rent in and around Lakeside?

Studio apartments may be small, but they pack a big punch when it comes to convenience and location. Put your bags down at one of these terrific studio apartments in and around Lakeside:

  • One of our favorite properties is "Perfect For Two A Little Hideaway In The Woods. Tiny House". Book a few nights or longer at this popular apartment and you'll have access to free toiletries and spa and beauty services.
  • An equally fantastic option is "Adorable Cottage New Buffalo, Mi. Near Grand Beach. 1 Bedroom". Don't be fooled by its modest size — this comfortable apartment is packed with handy amenities like a hair dryer, a bicycle and lots more.

Can I find short term rentals in or near Lakeside?

Whether you're looking for a chic apartment or a house big enough to fit the family, you'll find the perfect place on Vrbo. Sneak in a mini break at one of these favorite picks in or near Lakeside:

  • If you can only spare a few nights, "Book A Winter Getaway Warm Up By The Fireplace" is an excellent choice. It's not far from the center of Lakeside, so you'll be near all the best sights.
  • "Luxury Cottage With Pool; 2022 Summer Weekly Rentals Only" is also ideally located. Settle in here and discover why many guests rate this property highly.

What are the best romantic weekend getaways in or near Lakeside?

Nothing says "I love you" like a romantic weekend escape. If you're eager to spend a couple of nights away with your sweetheart, we've got some romantic getaways in and around Lakeside that will set your hearts aflutter:

  • Put on some soft music and slow dance the nights away at "5 Min. Walk To Mckinley St. Beach". Around 2 miles from Lakeside, this property has everything you could want for a couple's weekend away, including a fireplace and a nearby bay.
  • Another place where you can enjoy a few dreamy days together is "It's A Dog's Life" - Unleash Your Fun Here". Around 2 miles from Lakeside, a fireplace and beauty services add to the atmosphere here.

Are there mansions for rent in or near Lakeside?

You'll find some spectacular mansions for rent in and around Lakeside. If you're on the lookout for somewhere with plenty of space as well as that extra wow factor, these stunners will not disappoint:

  • Charm, elegance and oodles of character — "Lakefront Mansion With Heated Pool 9bedroom Modern Home On Private Sandy Beach" has it all. Approximately 2 miles southwest of Lakeside and offering beauty services and a swimming pool, this place is hard to beat.
  • Another popular option is "Lake Michigan Mansion And Coach House". Around 25 miles to the northeast of Lakeside, this opulent vacation rental gives you a taste of high-class living and comes with a firepit, beauty services and more.

What are the best large group vacation rentals in or near Lakeside?

Share your vacation and boost your odds of having fun. Whether you're planning an active escape with friends or a family reunion, you'll have your pick of large group vacation rentals in and near Lakeside:

  • Offering privacy, space and comfort, you'll get your guests' tick of approval at "New, Luxury Magnolia - Style Cottage". Up to 12 people can stay at this retreat which has 4 bedrooms, a swimming pool and a garden. You'll discover it around 6 miles to the southwest of Lakeside.
  • Invite as many as 12 of your dearest friends to "Relax And Enjoy. Walk To Beach And Restaurants" and fill its spaces with love and laughter. This popular option has 4 bedrooms and is around 6 miles to the southwest of central Lakeside. It's packed with features to keep your large group comfortable and content, such as a swimming pool and a fireplace.

What are the best houses for rent with a pool in or near Lakeside?

Of all the amenities a vacation rental can have, a pool delivers the most fun. Take a peek at these houses for rent with a pool in or near Lakeside and spend your days splashing around. Just remember to bring your unicorn floatie:

  • Get comfortable at "Beautiful Lake Michigan Beach House Near Beach Only 1 Hr 15 Mins From Chicago", where your biggest priority will be spending time in the pool. Amenities such as a barbecue grill and towels help make this retreat a favorite with guests.
  • Spend lazy vacation days splashing about or simply unwinding by the water at "Perfect For Two A Little Hideaway In The Woods. Tiny House". This property is also a firm favorite and features a stereo, a toaster and more.

Wondering what the weather's like in Lakeside? It has a humid continental climate, with average temperatures in summer ranging from 65 ºF to 75 ºF. If you're searching for more inspiration on where to stay in this popular destination, use the search bar at the top of the page and adjust the filters to check out our entire selection of Lakeside vacation rentals.

What are the best large family vacation rentals in or near Lakeside?

Whether your idea of the perfect escape is out in the country or on the beach, you'll have so much more fun if you share it with loved ones. Settle into one of these large family vacation rentals in or near Lakeside and bring the whole crew:

  • Invite your nearest and dearest to "Stones Throw' Lakeside Home - Walk To Marina + Town", which has 3 bedrooms that sleep up to 8 guests. This retreat is around 6 miles to the southwest of Lakeside and features amenities such as on-site watersports and childrens activities.
  • "Luxury Cottage With Pool; 2022 Summer Weekly Rentals Only" is another excellent option. It's about 6 miles to the southwest of Lakeside, has 4 bedrooms and accommodates up to 8 guests. Handy amenities here include a barbecue grill and a kitchen.

If you're looking for family-friendly attractions around the area, you have plenty of choice. Surfari Joe's Indoor Wilderness Water Park, Galien River County Park and Kids Quest promise lots of fun for young and old.