Vacation rentals with a kayak in Cook County

Find and book unique kayak rentals on Airbnb

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

Apartment in Chicago

4.96 out of 5 average rating, 79 reviews

The Holiday House by the Lake! 2br/2bth

Come enjoy the holidays at this incredibly festive and modern 2 br/2 bth garden unit steps from the beach! Large kitchen, perfect for entertaining. Bth 1 has body sprays & rain head shower and Bth 2 has a jetted bath. Walking distance to local bars, restaurants, Loyola & the Red line train stop. Garage parking is avail for $25 per night. You must reserve at the time of booking by sending a request as spaces are limited. Large vehicles may not fit-please send host vehicle’s model name/size

Top guest favourite

Home in Carol Stream

4.92 out of 5 average rating, 114 reviews

LakeHome Retreat- Hot Tub • Fire Pit • Bar & Games

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

Condo in Chicago

4.82 out of 5 average rating, 51 reviews

Cozy Kitties in the City 1BR by Park/Sox/Transit

This is my personal home in an 1890s Worker's Cottage, originally built for laborers in the Chicago Stockyards. It's offered below the going rate because looking after 2 friendly cats is part of the deal. This arrangement is not for everyone, but it comes with laughs and snuggles. Picture directions + all supplies provided. Great neighborhood with lots of green space - walk to everything you need! Super fast WiFi Free parking; Get downtown in 20 min by L train or via any of 5 nearby buses

Guest favourite

Camper/RV in Willow Springs

4.94 out of 5 average rating, 90 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

Guest favourite

Guest suite in Arlington Heights

4.93 out of 5 average rating, 55 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

Apartment in Chicago

4.94 out of 5 average rating, 87 reviews

Top Floor Portage Park Lookout

Welcome to our bright, and spacious top floor apartment in Chicago. Enjoy the park vibes while being centrally located to all that the city offers. Just minutes away from O'hare airport and public transportation, enjoy exploring Chicago's downtown and the hip shops, dining, and culture in surrounding neighborhoods like Avondale and Logan Square. Stylishly decorated, our open-concept space offers a large bedroom and a fully equipped kitchen. Book now for a perfect Chicago experience!

Superhost

Home in Downers Grove

4.94 out of 5 average rating, 48 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 🎤

Superhost

Home in Chicago

New place to stay

Walk to the Lake! Grill, Fireplace, Sleeps 12

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. Perfect for group stays, business travelers, or relaxing getaways, this stylishly updated space offers modern comfort in a peaceful neighborhood steeped in Chicago history.

Top guest favourite

Townhouse in Westmont

4.87 out of 5 average rating, 130 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.

Apartment in Glen Ellyn

4.68 out of 5 average rating, 31 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

Apartment in Forest Park

5 out of 5 average rating, 333 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.

Home in New Lenox

4.79 out of 5 average rating, 75 reviews

Family Friendly Farmhouse + Creek View!

Welcome to our totally remodeled modern farmhouse! The space features two bedrooms, two bathrooms, modern kitchen with quartz countertops, new appliances, and coffee bar. Additionally, it has a 55” tv, electric fireplace, PAC Man arcade, dedicated work space + laundry room. You’ll enjoy the large yard, creek view, kids swing-set, fishing spot, kayaks, & beautiful patio.