Beachfront holiday rentals in Cook County

Historic Coach House in Evanston Near Beach & Town

Stay in the Coach House of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire coach house which is renovated and includes a large bedroom with king bed and desk, a sun-filled living room/dining room, a full bath with claw-foot soaking tub and shower and a kitchen with amenities. The space can be equipped with an air mattress for an extra guest. Also available is a 3rd floor guest suite in the main house . Extra

Buena Vida Casa

Welcome to Buena Vida House. Step into a beautifully updated oasis where every detail has been thoughtfully designed to create a peaceful, stylish getaway. This all-new unit features fresh finishes, modern comforts, and a unique blend of beachy and boho vibes. Wake up just steps from the lakefront, ideal for morning jogs or simply soaking in the beauty of Chicago shoreline. This one-of-a-kind space offers comfort, charm, and convenience in one of Chicago’s most walkable and scenic neighborhoods

Steps from the beach and a mile from National Park

Perfect for family or friends to relax and enjoy Indiana’s Dunes National Park! The Holliday House is a 2022 custom built home with lake views and a beach path just STEPS from the front door! This 2000 sq ft open concept design features 3 bedrooms and 3 bathrooms, 16’ ceilings, open great room with beautiful indoor/outdoor kitchen, custom dining seating for 8, and loft hammock. Hosts live next door and are easily available if needed! Everything is on the 1st floor except for the 3rd bedroom.

Stone Mansion Sleeps 10-20 Free parking & TV

Giant, 4 bedroom, 2,300 square feet apartment on 2nd floor, near Red Line Train, bars, cafe's, shopping, restaurants, Lakefront and everything else Chicago has to offer. Large living room with bar area, TV and fridge for socializing before hitting the town. Dining room has a large table and 8 chairs. 4 bedrooms with 2 private rooms with king beds and one with a double bed. 4 futons for in the living room for extra sleeping space two (2) parking spots in the west facing garage on premises.

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

Smart Home, Hot Tub, direct Beach/Nat’l Park access, luxury amenities

The Addition at Villa Santorini offers relaxed luxury, where soaring ceilings, expansive views, and curated amenities invite you to unwind and slow down. Perfect for small family gatherings, a romantic retreat, or time with close friends, this inviting space makes everyone feel at home. With Lake Michigan and the Indiana Dunes National Park right outside and Chicago just 40 minutes away, this peaceful and convenient home base provides the ideal setting (and permission) to recharge in style.

Beachfront- Lake Michigan- 2bd/2bath -Heated Pool

Lake Michigan - Beachfront w/heated in-ground Pool - Indiana Dunes National Park - Private Basement Guest Suite- 2 Bedroom/2 Bathrooms-Newly Renovated and Beautifully Decorated- Heated In ground Pool* Below Deck at Waters Edge has everything you need to have a comfy and relaxing stay with your family or friends. Hiking, Beaches, X-Country Skiing and so much more! Less than an hours drive to Chicago. *Heated Pool Open from Mid-May to Mid Oct. Pool closed until Mid-May 2024.

Miller Mermaid Suite-100 yds from the beach!

100 yds from the beach, the cozy MERMAID SWEET awaits you and is well suited for a young family or 2-3 adult friends. This artsy basement open studio space includes a private entrance, kitchenette, unique art & a cozy reading/sleeping nook! Enjoy beautiful sunsets from the upstairs deck. BBQ on the grill. Visit local restaurants, shops & galleries. Hike wooded trails & swim by sandy, dune-grass beaches. . House-trained dogs welcome! Sorry no cats (allergies)

Pool & Beach Haven-private pool, steps to beach!

Come enjoy this beautiful newly renovated home with large in ground pool steps from the beach & Lake Michigan. Spacious patio with various seating areas to relax, enjoy cocktails & dining by the pool. You will be so thrilled to be <100 steps to our lovely beach-with private beach entrance at end of the block. National Park a mile away! 1/2 day at the beach, 1/2 day by your private pool? Luxurious decisions…What more can you dream of for a vacation or retreat?