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Destination guide

Head to the historical city of Lakeside

The area's architecture and history are just some of the reasons to come on holiday to Lakeside. This city's lake, beaches and forests draw many visitors. Take in top local attractions such as Indiana Dunes National Park and Lake Michigan. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Things to do

Activities and attractions in and around Lakeside

Do you want to discover things to do during your stay? Venture out of your cosy holiday rental and experience everything that Lakeside has to offer. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Local (5.2 mi / 8.3 km)
  • Round Barn Winery (11.9 mi / 19.1 km)
  • Shady Creek Winery (12 mi / 19.2 km)
  • Washington Park Zoo (14.7 mi / 23.7 km)
  • Round Barn Union Pier Tasting Room (1.5 mi / 2.4 km)
  • Captain Mike's Fun Park (6.8 mi / 10.9 km)
Natural features

Exploring the natural features in Lakeside

Whether you're looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Lakeside. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Indiana Dunes National Park (24.6 mi / 39.6 km)
  • Warren Dunes State Park Beach (5.1 mi / 8.2 km)
  • New Buffalo Public Beach (5.3 mi / 8.5 km)
  • Warren Dunes State Park (6.3 mi / 10.1 km)
  • Weko Park (7.8 mi / 12.5 km)
  • Washington Park Beach (14.7 mi / 23.6 km)
How to get there

Travelling to and around Lakeside

Fly into Chicago Midway Airport (MDW), the closest airport, located 55.4 mi (89.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into South Bend, IN (SBN-South Bend Intl.), which is 21 mi (33.8 km) away.

What are the top holiday 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 favourite 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 holiday rental for you.

What are the top-rated holiday 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 favourite 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 favourite 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 centre 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 holiday rental gives you a taste of high-class living and comes with a firepit, beauty services and more.

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

Share your holiday 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 holiday 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 holiday 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 favourite with guests.
  • Spend lazy holiday 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 favourite 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 65null to 75null. 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 holiday rentals.

What are the best large family holiday 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 holiday 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.

Can I find family cabin rentals in or near Lakeside?

Escape the daily grind and treat the people you love to a different sort of holiday. Stay in one of these family cabin rentals in or near Lakeside and get the camping experience — but with all the comforts of home!

  • "Cabin - Inspired By Renewal, Designed W" - Located about 4 miles northeast of the centre of Lakeside, this family-friendly retreat offers amenities like childrens activities and a garden.
  • "Mi Wine Trail - Tiny Cabins - Big Experiences" - Gather up the troops and spend a few nights or more at this inviting rental, which is around 2 miles to the northeast of Lakeside. You'll have access to free toiletries, a microwave oven and a great deal more.

For more options, use the search bar at the top of the page and adjust the filters to find the Lakeside holiday rental that's perfect for your needs.