Vacation rentals with a kayak in Cook County

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Top-rated kayak rentals in Cook County

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Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 75 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

Condo 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 favorite

Camper/RV in Willow Springs

4.94 out of 5 average rating, 79 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 favorite

Home in Prospect Heights

4.91 out of 5 average rating, 56 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!

Guest favorite

Guest suite in Arlington Heights

4.92 out of 5 average rating, 53 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 favorite

Home in Carol Stream

4.92 out of 5 average rating, 111 reviews

LakeHouse Stay! Hot Tub-Bar-Kayak-pool table-darts

Our beautiful home is the perfect place to gather with friends & family, relax, refresh, fish, have fun with your loved ones. It's the perfect home away from home with great views of the lake and on a quiet cul-de-sac. Stunning views of the lake while grilling or the firepit from the completely upgraded patio & the hot tub 🥂 🐶Up to 2 furry babies are allowed & they'll love the almost 1 acre fenced-in yard! (pet fee is extra & must be included at time of booking)

Guest favorite

Home in Downers Grove

4.93 out of 5 average rating, 43 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 🎤

Guest favorite

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.

Superhost

Apartment in Glen Ellyn

4.71 out of 5 average rating, 28 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 favorite

Apartment in Forest Park

5 out of 5 average rating, 321 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.

Guest favorite

Home in New Lenox

4.82 out of 5 average rating, 71 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.

Home in Westmont

4.74 out of 5 average rating, 34 reviews

Cozy 5-bedroom with lake views and spacious deck

Enjoy vacation views in the western suburbs, when you book this spacious 5 bedroom 2.5 baths. Conveniently located between Oak Brook, Hinsdale and Clarendon Hills, you'll find no shortage of parks, restaurants and entertainment nearby. With a fully stocked kitchen, office space, a 2-car garage and child-friendly rooms, this property is a fantastic fit for your family!