The Best Vacation Rentals to Book in Illinois

Serenity 41W is a spacious, sleek townhouse on the Illinois River
Serenity 41W is a spacious, sleek townhouse on the Illinois River | Courtesy of Serenity 41W / Expedia
Photo of Rosanna Stevens
9 November 2021
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From the Chicago skyscrapers on the shores of Lake Michigan to quaint villas along the Illinois River, visitors to the Prairie State have a great choice of vacation venues, with townhouses that place you next to the action, riverside villas with the marina lifestyle and contemporary homes for group trips. Whether you’re looking for a base in the city or a waterside haven, here’s our pick of vacation rentals in Illinois – bookable on Culture Trip.

Three-level Bucktown home, for outdoor dining and stylish living space

Lounge at Three-level Bucktown home vacation rental in Bucktown, Illinois
Courtesy of Three-level Bucktown home / hotels.com

The large double bedrooms in this house in this stylish Bucktown home are spread over two floors with varnished wooden floors and stylish touches, roll-top baths and exposed brickwork. Downstairs, watch dinner come together while perched at the kitchen island – or on warmer days, the garden with outdoor kitchen and seating area is the perfect place to gather. Guests in search of a Chicago deep dish will love the proximity to the much-loved family-owned restaurant My Pi Pizza.

Toes in the Water, for riverfront family living

Room at Toes in the Water vacation rental in Heritage Harbor, Illinois
Courtesy of Toes in the Water / Expedia

As the name suggests, this fun, nautical-inspired home on the banks of the Illinois River in Heritage Harbor is perfect for dipping your toes in the water. Bunk beds in the second bedroom make this vacation rental ideal for small families, and with on-site amenities including an outdoor pool, there is plenty to do other than watch the boats go by from the deck. You’ll find everything you need to cook family dinners here – or try the Red Dog Grill on the marina for a night out.

Harbor Haven, for a couples getaway

Living space at Harbor Haven vacation rental in Heritage Harbor, Illinois
Courtesy of Harbor Haven / Expedia

Escape to the waterfront for a couples getaway in Heritage Harbor. Accommodating four guests, this vacation rental in Illinois with two double bedrooms and two bathrooms has chunky rustic furniture and a quaint kitchen with a dining table under a hand-blown pendant light. Lounge the day away on a pontoon boat or sit around the firepit, before coming back for a drink on the deck.

Sunriver, for the rolling views

Exterior of Sunriver vacation rental in Heritage Harbor, Illinois
Courtesy of Sunriver / Booking.com

Buttercup yellow and sitting on a lawn that rolls down to the water, this quiet one-bedroom vacation rental in Heritage Harbor lives up to its name. Watch the sun setting behind the river bend from the deck or curl up on the squishy corner sofa and catch up on a box set. It’s even pet-friendly, so furry friends can join in the fun.

Windy City Wanderer, for seeing the sights of Chicago

Living space at Windy City Wanderer vacation rental in Lincoln Park, Chicago, Illinois
Courtesy of Windy City Wanderer / Hotels.com

This two-bedroom apartment is conveniently located if you’re looking for a vacation rental close to DePaul University. Memory foam beds, exposed brickwork and a compact kitchen dining area make it a cozy place to stay with a lot to explore nearby. Sports fans can catch a game of baseball at Wrigley Field – or explorers can head to Lincoln Park Zoo or the Chicago History Museum.

Kindred Spirit #7P, for river-based adventures

Exterior of Kindred Spirit #7P vacation rental in Heritage Harbor, Illinois
Courtesy of Kindred Spirit #7P / Booking.com

Sleeping up to six guests in two double bedrooms and an extra sofa bed, this comfortable home in Heritage Harbor is ideally placed for all the activities on offer. For the adventurous, there’s kayaking, kite flying, hiking and even skydiving. Or take a more sedated approach and spend the afternoon craft beer or wine tasting. And when you just want some me time, chill at home and watch the world go by from your sunny porch – it’s your vacation, after all.

Casa Margarita #224, for light and stylish living on the water

Lounge at Casa Margarita #224 vacation rental in Ottawa, Illinois
Courtesy of Casa Margarita #224 / Expedia

The teal wooden fronting on this vacation rental perfectly reflects the river, and the interior has been given just as much thought. A light and airy spot, Casa Margarita is a two-bedroom, two-bathroom vacation rental on the water’s edge. Open-plan living, neutral earthy tones and elegant design touches such as wooden floors, paneled doors and linen headboards make this a stylish home from home.

Harbor Master Villa #230, for its prime position

Exterior of Harbor Master Villa #230 in Ottawa, Illinois
Courtesy of Harbor Master Villa #230 / Booking.com

Watch the comings and goings in the marina from this one-bedroom villa, wandering straight out onto your private deck from bed. Downstairs, a kitchen with breakfast nook and cozy sitting room makes this vacation rental the perfect spot for two – but with the option of inviting a friend to stay on the sofa bed and enjoy the views with you.

Serenity 41W, for a townhouse on the water

Bedroom at Serenity 41W vacation rental in Ottawa, Illinois
Courtesy of Serenity 41W / Expedia

Spacious and contemporary, this townhouse on the Illinois River close to Ottawa sleeps up to eight people and delivers everything you want from a vacation. All bedrooms have a view of the water and there’s even a bar for fixing sundowners to enjoy on the large deck. This vacation rental comes with parking and enough attractions and activities nearby to keep everyone entertained – including kayaking, fishing and boat trips.

River House, for group getaways

Lounge space at River House vacation rental in Ottawa, Illinois
Courtesy of River House / Expedia

This pet-friendly riverfront home offers plenty of living space for larger groups. A double-height kitchen and living area complete with a chandelier and open fireplace seem like the center of the action – until you discover the games room upstairs with its own bar, plump sofas and card table. For quieter moments, bask in the sunny reading nook overlooking the water, or on the rear deck that backs onto it.

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