Vacation rentals with a kayak in Cook County

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

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

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

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!

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.

Family Friendly Farmhouse + Arcade + Creek View!

Welcome to our beautifully renovated modern farmhouse! This thoughtfully refreshed unit offers two bedrooms, two bathrooms, a modern kitchen with quartz countertops, brand-new appliances, and a welcoming coffee bar. Enjoy a 55” TV, electric fireplace, PAC-MAN arcade game, dedicated workspace, and a full laundry room. Step outside to a large yard with scenic creek views, a kids’ swing set, a relaxing fishing spot, and a charming patio—perfect for unwinding or making memories with family.

Luxury Lakefront Retreat w/ Chicago Skyline Views

Luxury Lakefront Retreat with Chicago Skyline Views & Sauna Welcome to a refined lakefront escape designed for guests who value privacy, comfort, and unforgettable scenery. This modern home is directly on the water, offering uninterrupted views of Lake Michigan and the Chicago skyline. Thoughtfully designed for families, couples, and professionals, this property delivers a peaceful, upscale experience in one of the most scenic waterfront locations in the area.

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 🎤

Near Lake & Museum • Modern • Game Area

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.

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.

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.

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.