Holiday rentals with a kayak in Cook County

Find and book unique kayak rentals on Airbnb

Top-rated rentals with kayak in Cook County

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

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Top guest favourite

Home in Carol Stream

4.93 out of 5 average rating, 124 reviews

Lake Home Retreat! HotTub• FirePit• Kayak• 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

A black leather sofa sits adjacent to a round, gold accent table, providing a comfortable seating area. An open layout showcases a dining table set for four, with a colorful rug beneath. The kitchen is visible in the background, featuring wood cabinetry and stainless steel appliances.

Apartment in Des Plaines

Exquisite Haven:Beautiful 3bedroom 1.5bathTownhome

Welcome to this charming and spacious 3-bedroom, 1.5-bathroom apartment, designed to offer both comfort and style in a peaceful, convenient setting. As you step inside, you’ll be greeted by an open floor plan that effortlessly connects the living, dining, and kitchen areas. perfect for relaxation or entertaining guests. What truly sets this apartment apart is its perfect blend of comfort and functionality with an indoor Washer and dryer to yourself. Also there is private backyard for relaxation

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 van/Motorhome 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.

Superhost

The room features a queen size bed adorned with patterned bedding and surrounded by nature-themed decor. A sleek wall-mounted TV is positioned above the headboard, while vibrant red and geometric black accents create a modern atmosphere. Wooden floors complement the overall design.

Private room in Maywood

4.94 out of 5 average rating, 82 reviews

Everything You Need and a Little More

Vintage home with an eclectic touch of modern in a quiet family neighborhood on a tree lined block; very close to forest preserves, shopping, public transportation, and easy access to many hospitals (for medical students), Chicago, Forest Park, Oak Park, and O'Hare. Home will be shared with a married m/f couple (owners) and permanent female renter. There are 3 rooms total available in our home through Airbnb through separate listings. Generally, two bedrooms per bathroom.

Guest favourite

A wooden dock extends into the calm water, framed by lush greenery and trees. Two metal chairs sit on the dock, offering a serene spot to enjoy the lake views.

Home in Downers Grove

4.94 out of 5 average rating, 64 reviews

Lakefront View Getaway Home! Hot tub! Kayak!

INCREDIBLE 5,519 sq. LAKEFRONT HOME with GORGEOUS VIEWS. 30 Minutes Away From Downtown Chicago. 7 Bedrooms, 9 Beds, 2 Additional Sofa Beds & 4 Baths. Fits 20 guests by request. PRIVATE DOCK and PATIO/BACKYARD Right on BROOKERIDGE LAKE. UNICORN ISLAND FLOATING RAFT, KAYAK, PADDLE BOAT, FISHING & MORE. BrookeRidge Private Jet Airport in the Same Park. Indoor Entertainment Including POOL TABLE, AIR HOCKEY, PING PONG, DARTS, CARD GAMES, GAMING CONSOLE & KARAOKE 🎤

Top guest favourite

A glass of red wine is positioned in the foreground, reflecting the soft colors of the sunset over a calm lake. The shoreline is bordered by tall grasses, framing the tranquil water and vibrant sky.

Townhouse in Westmont

4.87 out of 5 average rating, 132 reviews

Westmont 3/2 duplex Fire sunsets, Firepit, lake

Near great shopping and dining. Enjoy wonderful sunsets and quiet lake activity. Fully Stocked 20 acres lake with a neighborhood beach next door. Easy commute to downtown while enjoying the peace and quiet. Feel like you are on vacation every day. Perfect for a staycation. Cleaned to Cdc standards. This duplex is a gem in Western suburbs! Pet friendly (fee). Fire pit (bring Wood), paddleboat, kayaks. Grill and fully stocked kitchen.

Guest favourite

The bedroom features a cozy bed dressed in blue and white patterns, complemented by a plush area rug. A large mirror and decorative furniture are present. Natural light enters through the windows, and a chandelier adds soft illumination overhead.

Private room in Franklin Park

4.94 out of 5 average rating, 269 reviews

Beautiful Master Clean & Safe Near Ohare Rosemont

・"The best place isn't the most luxury one, is the place where the host share everything." Bright and cheerful Room Furnished with all necessities for a short trip Private Bath-tub, Smart 50 Inch TV, Wifi,Parking, Near Bus Stop/Train Station Walking to Restaurants, Supermarket, 5 minutes drive to: " Rosemont Theater, Donal E Stephen Center, Fashion Outlet Shopping Mall, (ORD) O'Hare Airport, Casino & Allstate Arena",

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.

Flat 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.

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.

Flat in Forest Park

5 out of 5 average rating, 368 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.