Vacation rentals with a kayak in Cook County

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Top-rated accommodations with a kayak in Cook County

Guests agree: these accommodations with a kayak are highly rated for location, cleanliness, and more.

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Top guest favourite

A warm living room features a brick fireplace as the focal point, framed by two arched windows allowing natural light. Comfortable seating arrangements include a plush sofa and armchairs, complemented by a wooden coffee table. A children's playhouse adds a touch of whimsy to the space.

Home in Carol Stream

4.93 out of 5 average rating, 123 reviews

LakeHome Cozy Retreat! HotTub •FirePit•Bar•Fishing

Come enjoy our beautiful home it's the perfect place to relax, unwind & enjoy peaceful lake views. Whether you’re fishing, soaking in the hot tub or sipping coffee on the deck, it’s a quiet home away from home on a serene cul-de-sac. Enjoy stunning views of the lake while grilling or relaxing by the firepit on the beautifully landscaped patio & in the hot tub 🥂 🐶 Up to 2 furry babies are welcome & they’ll love the almost 1-acre fenced yard! 🌅 See weekly & monthly discounts for longer stays

Guest favourite

A cozy sleeping area features a spacious bed with an intricately patterned quilt. Natural light filters in through window frames, illuminating the room's warm wood accents. A kitchenette is adjacent, showcasing a coffee maker and a compact stove beneath overhead storage.

Camper/RV in Willow Springs

4.95 out of 5 average rating, 91 reviews

Wander Willow Springs Glamping Retreat

Nestled in the serene landscapes of Willow Springs, the Wander Willow Springs RV offers a peaceful and immersive getaway. Relax in a cozy, fully-equipped stationary RV. Unwind in nature's embrace, just 1 block from Chicagoland's largest forest preserve. Immerse yourself in the tranquility of your surroundings while savoring a cup of coffee on the outdoor patio w/fire pit, explore the forest's miles of hiking and biking trails or the village's charm from the comfort of your own private retreat

A modern farmhouse exterior is surrounded by vibrant greenery, showcasing large windows that invite natural light. The welcoming entrance features a contemporary design with black fencing, and a paved driveway provides ample space for parking.

Home in New Lenox

4.72 out of 5 average rating, 98 reviews

Family Friendly Farmhouse + Arcade + Creek View!

Welcome to your modern farmhouse retreat, freshly renovated with comfort and style in mind. This updated 2 bed, 2 bath unit features a sleek kitchen with quartz countertops, new appliances, and a cozy coffee bar. Relax with a 55 inch TV, electric fireplace, or PAC MAN arcade. A workspace and laundry add convenience. Outside, enjoy a spacious yard with creek views, swing set, patio, and private fishing spot. Perfect for families, couples, or extended stays seeking comfort, fun, and relaxation.

Guest favourite

The exterior of a two-story brick home is viewed from a well-maintained lawn. A wooden deck extends from the house, with surrounding greenery complementing the serene lake in the background under a clear blue sky.

Home in Prospect Heights

4.92 out of 5 average rating, 64 reviews

Bike & Kayak: Lakefront Prospect Heights Home

2 Soccer Goals w/ Soccer Balls | BBQ Ready | 2 Mi to Train Station | < 30 Mi to Chicago Explore nature or suburban and city attractions when you stay at this lakefront vacation rental in Prospect Heights. Located 2 miles from the train and less than 30 miles from Chicago, the 4-bedroom, 3.5-bath home makes it easy to access endless activities. Take the kayaks out on the lake across the street, stroll through The Grove, book a tee time at Old Orchard Country Club, or cool down at Lions Pool!

Top guest favourite

A bright living space features a spacious sectional sofa accented with blue and white cushions. A round coffee table sits atop a decorative rug. A large clock adorns the wall, while a dining area with a wooden table and chairs is visible in the background.

Guest suite in Arlington Heights

4.95 out of 5 average rating, 76 reviews

Cozy Chicago Suburban Apartment

Welcome to our cozy apartment, perfect for solo travelers or couples looking for a comfortable stay in the quiet Northwestern suburbs of Chicago. Located in a quiet and serene neighborhood, this apartment offers easy access to all the best restaurants, cafes, and shops. Just 23 mins away from O’hare International Airport, 15 mins to Schaumburg Convention center & Woodfield Mall, and about 40 mins from the Chicago Downtown. Lake Arlington is a 10 mins walk away for Kayak and park activities.

Top guest favourite

A living area features exposed brick walls and polished hardwood floors. A comfortable sofa along with two wooden side tables, each topped with a lamp, is positioned for relaxing. Large windows allow natural light to fill the space, providing views of the outdoors.

Guest suite in Chicago

4.88 out of 5 average rating, 199 reviews

The Huron Haven

A beautiful, one-of-a-kind, hidden gem in the heart of River West. Private entry. Front & Back Patios. Full office space. Large Living Room. Exposed brick walls, 11.5’ tall ceilings. Large barn doors lead from the living room / office to a large master bedroom with large modern bathroom. The bedroom has French doors which open to private balcony with a beautiful back patio, dining space, and thriving garden. On Property Parking

A cozy living area features a green sofa with accent pillows, complemented by two mustard-yellow chairs and a glass coffee table. Natural light illuminates the space, highlighting the hardwood floors and decorative wall art. Built-in shelves display books and plants, contributing to a welcoming atmosphere.

Apartment in Glen Ellyn

4.7 out of 5 average rating, 37 reviews

Enchanting 2 BR + Office/BR in Heart of Town

Enjoy a charming experience at this centrally-located maisonette in the heart of Glen Ellyn. Built in the early 1900's, the 2nd floor apartment features natural sunlight, hardwood floors, built-in shelves, and cozy nooks. Centrally located, walk to all the restaurants, shops, and bars the village has to offer. Less than a block from the apartment, the metro stop is just a 40 minute ride into downtown Chicago.

Home in Chicago

4.56 out of 5 average rating, 18 reviews

Near Lake & Museum • Modern • Game Area

Welcome to 76th Chicago 535 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. Stylish South Shore Escape | Walk to Lake, Near Hyde Park & Downtown. Welcome to your home away from home in South Shore, Chicago, just a 5-minute walk to Lake Michigan and a quick drive to Hyde Park, the Museum of Science and Industry, and the future Obama Presidential Library.

Top guest favourite

A spacious bedroom features a large bed with dark bedding and decorative pillows. A wooden bookshelf filled with books stands against one wall, while sunlight filters through a window adorned with light curtains. A vintage dresser and bedside table complete the welcoming space.

Apartment in Forest Park

5 out of 5 average rating, 367 reviews

Like a Treehouse!

If you're coming to Illinois for any medical procedure that's no longer available in your home state, reach out to us about discounts. You'll feel like you're in a tree house in our 850 sq ft coach house, above our workshop/garage, behind our home in historic Forest Park, right next to Oak Park. Just 8 miles west of Downtown Chicago, convenient to I-290 and the Blue Line train.

The living room features a cozy seating arrangement, including a sectional sofa and two accent chairs. Large windows with sheer curtains allow natural light to enter, creating a bright atmosphere. A circular coffee table sits on a dark area rug, enhancing the contemporary decor.

Apartment in Des Plaines

4.17 out of 5 average rating, 18 reviews

Charming Retreat In the Heart of Des Plaines

Welcome to the Charming Retreat on Oakwood Avenue in the Heart of Des Plaines . This inviting property offers a peaceful retreat for family adventurers, couples, solo travelers, and business travelers seeking a serene, contemporary and comfortable space. Step inside and discover a hotel-like atmosphere where every detail has been thoughtfully considered.

Guest favourite

Four kayaks in bright colors—red, yellow, and blue—are positioned on the lush green lawn. The kayaks are neatly arranged, with the serene Marquette Park lagoon visible in the background, framed by trees and greenery.

Home in Gary

4.94 out of 5 average rating, 204 reviews

Kayaker's Dune Cottage

Tucked in among the Indiana Dunes National Park, this charming split-level ranch home is only a short walk from the beach and backs up to the Marquette Park lagoon. Kayakers can launch right from the backyard! We provide 5 kayaks (3 adult, 2 child), life jackets, and paddles to our visitors.