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6 scenic lakeside retreats perfect for warm weather

Rent an artsy A-Frame, secluded cottage, or campy bunkhouse

A red cabin with a barn-like aesthetic, four rectangular windows, and two bay windows faces an open yard with a small paved sidewalk and ramp that follows the edge of the woods.
Just on the other side of the cottage are stunning views of Lake Michigan.

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When the weather gets warm, Chicago bursts with energy: There are weekly fireworks, street festivals, and a never-ending stream of events. Escaping to the quieter corners of the city, or visiting a secret park, may not be enough of a break from the crowds. What better place to cool off and relax than one of the region’s lakeside retreats?

While Door County and Indiana Dunes are perfect for summer, Lake Michigan isn’t the only place for a getaway. And just a few hours away is Chain O’ Lakes State Park.

Below, we’ve rounded up vacation rentals that will help you get some peace and quiet by the water. For more local travel, check out our map of small towns just a short drive away from Chicago.

A small white wood paneled cottage with three rectangular windows below the grey roof and a cedar wood door with two wider, green-trimmed windows below.
A recently renovated, 100-year-old home in Wisconsin.

Lakeview Cottage in Baileys Harbor in Door County, Wisconsin

This nautical-themed cottage in Door County is just on the edge of downtown, and has a view of Lake Michigan. There’s a brewery and coffee shop within walking distance, but with a vacation rental like this it’ll be hard to leave. The recent renovation of the century-old home features brand-new beds, a light-filled open kitchen, and a new flagstone patio. Sleeps up to eight at $370 per night.

A small green cabin with white trim windows and a red door. Painted canoe paddles and a white throw ring are decoratively hung on the side of the woodsy cabin.
The two-story bunkhouse nestled into a hill overlooks the lake.
Airbnb/Camp Wandawega

Camp Wandawega Top Bunkhouse in Elkhorn, Wisconsin

Camp Wandawega started out as a speakeasy, and eventually fell into the hands of the current owners, who have worked to restore the old cabins, houses and bunks on site. The 1920s bunkhouse is ideal for big groups, especially with so much to do around camp: There’s a treehouse lounge, grills and smokers, 25 acres of untouched woods, a private beach with rowboats, campfire pits, and retro Schwinn bikes. Sleeps up to 12 for $1,100 per night.

Tall trees shade a grassy backyard with Adirondack chairs, firepits, and a woven hammock. A grand two-story white and sky blue house overlooks the lake.
Hammocks and firepits—what more could you need?
Cypress Resort and Marine / Airbnb

Petite Lake house in Antioch, Illinois

Another easy, lakeside retreat. This property sits on a grassy hillside overlooking Petite Lake, part of the Chain O’ Lakes region. The cottages and lake house here were built in the 1900s which the family owners have rehabbed. There’s lots of campy fun—make s’mores around a campfire, take water skiing lessons, or rent a pontoon boat. Sleeps two for $150 per night.

An A-frame cabin with a red roof, black wood balcony, and brick chimney sits in the middle of a lush green forest with bright green ferns and tall trees.
The rental here has a private beach.

Artsy A-Frame in Sawyer, Michigan

This secluded A-Frame in Sawyer, Michigan will give you all the magic of the state’s sand dunes without the crowds. The home sits on a lush ravine with tall trees and small creek. You’ll have access to a private path that leads to a secluded half-mile stretch of beach. The home is great for families with an 10-seat indoor dining table, a ping-pong table, a fireplace, and screened-in porch. Sleeps up to 10 for $365 per night.

A bright pink house with white trim and two white balconies sits between two tall green trees.
This rental comes with a hot tub and golf cart.

Pink Cottage near Indiana Dunes

This eye-catching, newly built home in Long Beach, Indiana was made for a beachy getaway. The home is a half-mile from the lake, but you can drive a golf cart and park it right at the beach. The kitchen, with a large island and dining room table, is the perfect place to congregate for board games or happy hour. Retreat to the coach house, second-floor balcony, or hot tub for some quiet time. Sleeps up to 19 for $550 per night.

A red cabin with a barn-like aesthetic, four rectangular windows, and two bay windows faces an open yard with a small paved sidewalk and ramp that follows the edge of the woods.
Just on the other side of the cottage are stunning views of Lake Michigan.

Red cottage in Bridgman, Michigan

This private lakefront cottage sits all the way at the end of a road surrounded by a forest of tall trees. Each of the house’s levels has a living area and decks overlooking the wooded dunes, sandy beach, and calm water. Get toasty on cool nights in front of two wood-burning fireplaces or start enjoy a woodsy bonfire on the patio outside. The views are stunning here, and you’ll also get nearly 200-feet of Lake Michigan beach to yourself. Sleeps 10 for $520 per night.