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

An outdoor patio is illuminated by string lights, creating a cozy ambiance. The hot tub is set against a backdrop of snowy ground, with comfortable seating arrangements nearby. The lake is visible in the background, enhancing the tranquil atmosphere.

Home in Carol Stream

Lake House Escape •Hot Tub, Bar, Fishing, Firepit

Visiting Chicago this holiday season? Stay somewhere that truly feels like home. We’re opening our personal lake home to guests & would love to welcome u! Tucked awayi n a peaceful neighborhood- the perfect place to gather w/ family, relax & enjoy beautiful lake views. Spend mornings w/ coffee on the deck, afternoons fishing, grilling & evenings soaking in the hot tub or sitting by the firepit. 1-acre fenced yard to enjoy-pets welcome Come settle in, make memories & enjoy our home as your own. ♡

LocationValueWifi

4.92 out of 5 average rating, 128 reviews

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 Plains

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

Top 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

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

LocationValueParks

4.94 out of 5 average rating, 101 reviews

Guest favourite

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

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.

ValueLocationHospitality

4.76 out of 5 average rating, 118 reviews

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

Family-Friendly Lake Home in Quiet Neighborhood

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!

ValueOutdoor spacesWalkability

4.93 out of 5 average rating, 67 reviews

Top guest favourite

Home in Des Plains

Home with spa by O'Hare Airport

Classic Chicago bungalow near downtown Des Plaines that has been remodeled for style and comfort. There is a 6-person spa (hot tub) with a full recliner seat in the backyard. Located directly next to a public park with large playground and basketball half court to entertain your family. Close proximity to multiple highways to quickly take you in any direction including into Chicago. The UP-NW Metra line is 1 mile away for easy access to downtown Chicago.

ValueOutdoor spacesCleanliness

5.0 out of 5 average rating, 17 reviews

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 West Town

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

ValueOutdoor spacesPets

4.87 out of 5 average rating, 233 reviews

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

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.

Outdoor spacesLocationGrill

4.87 out of 5 average rating, 133 reviews

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

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",

Outdoor spacesValueHot tub

4.94 out of 5 average rating, 274 reviews

Guest favourite

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

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.

LocationValueCheckout

4.74 out of 5 average rating, 46 reviews

Home in South Side

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.

LocationNearbyHospitality

New place to stay

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

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.

LocationValueQuiet

5.0 out of 5 average rating, 394 reviews